💖100 worst romantic comedies of all time

Warner Bros.

#100. Her Alibi (1989)

- Director: Bruce Beresford
- Stacker score: 44.6
- IMDb user rating: 5.8
- Metascore: 24
- Runtime: 94 minutes

A "bad" mystery writer (Tom Selleck) gets swept up by the affections of Nina (Paulina Porizkova), a beautiful immigrant he presumes is wrongfully accused of murder until a series of failed gimmicks raise doubts in this forgettable 1989 farce. Roger Ebert gave it a half-star, calling it "endless, pointless, and ridiculous." It grossed only $18 million at the domestic box office.

Gold Circle Films

#99. Over Her Dead Body (2008)

- Director: Jeff Lowell
- Stacker score: 44.6
- IMDb user rating: 5.2
- Metascore: 30
- Runtime: 95 minutes

The plot revolves around a ghost (Eva Longoria) trying to sabotage a relationship between her former fiance (Paul Rudd) and a psychic (Lake Bell). Critics called it a lightweight "Ghost" and found the pacing slow, the plot implausible, and the characters lacking in charm. Making only $7.6 million, this one vapored off the mortal plane without leaving much of a trace.

Universal Pictures

#98. Nutty Professor II: The Klumps (2000)

- Director: Peter Segal
- Stacker score: 44.6
- IMDb user rating: 4.4
- Metascore: 38
- Runtime: 106 minutes

Fewer things seem more incompatible than Eddie Murphy's juvenile sense of humor and a love story. But the producers of "Nutty Professor II: The Klumps" were determined to try and wed the two. The end result was a film that critics called "shrill, obnoxious, unfunny, and nearly unwatchable." Even Janet Jackson's sweet portrayal of a DNA researcher who is head over heels for Murphy's Professor Klump wasn't enough to save this one.

Columbia Pictures

#97. Zookeeper (2011)

- Director: Frank Coraci
- Stacker score: 44.6
- IMDb user rating: 5.2
- Metascore: 30
- Runtime: 102 minutes

Kevin James—is there an actor alive whose box office success is more incongruous with critics' distaste for his movies? In this PG rom-com, James plays a kindly zookeeper who discovers animals can talk—and offer courtship advice—when he considers quitting his job, and his wards are forced to break their code of silence. Film critic Leonard Maltin thought it was a step up from James' previous project, "Paul Blart: Mall Cop," but the majority of reviewers disagreed. The picture grossed $80.4 million domestically, less than its production budget, but strong overseas numbers brought its international total to a profitable $169.8 million worldwide.

Twentieth Century Fox

#96. Just Married (2003)

- Director: Shawn Levy
- Stacker score: 44.6
- IMDb user rating: 5.4
- Metascore: 28
- Runtime: 95 minutes

The late Brittany Murphy stars with Ashton Kutcher in this lovable 2003 comedy about two newlyweds navigating the realities of holy matrimony on their honeymoon while a number of issues bubble up—some funny, some not. A box office success, critics were not impressed with the predictable storyline, and both actors earned Razzie Award nominations individually and as a couple.

Columbia Pictures

#95. Bewitched (2005)

- Director: Nora Ephron
- Stacker score: 44.6
- IMDb user rating: 4.8
- Metascore: 34
- Runtime: 102 minutes

On paper, "Bewitched" seems to have all the right ingredients for a successful rom-com: an experienced writer and director (Nora Ephron), a talented and exciting cast (Will Ferrell, Nicole Kidman, Shirley MacLaine, Michael Caine, Jason Schwartzman, Kristin Chenoweth, and Steve Carell) and a unique storyline inspired by the classic sitcom of the same name (a washed-up actor discovers his cute new co-star is a witch). But in the end, the film was missing that little bit of magic that would have taken it from theoretically great to actually great. The New York Times called it "an unmitigated disaster," and fans lamented its lack of direction and reliance on special effects over quality performances.

Universal Pictures

#94. Little Fockers (2010)

- Director: Paul Weitz
- Stacker score: 44.6
- IMDb user rating: 5.5
- Metascore: 27

The third installment in the "Meet the Parents" franchise, "Little Fockers" reunites the original cast for one last family row. Critics complained that the film— which was commercially quite successful, bringing in more than $310 million at the box office worldwide—was too formulaic, and its jokes too tired.

Columbia Pictures

#93. Mr. Deeds (2002)

- Director: Steven Brill
- Stacker score: 44.6
- IMDb user rating: 5.8
- Metascore: 24
- Runtime: 96 minutes

In this Frank Capra remake, a small-town man is left the keys to the kingdom after the death of a wealthy relative and must sort out who loves him for him and who loves him for his money. Starring Adam Sandler and Winona Ryder, the film was disparaged by critics for the way it dumbed down its source material, taking the story from smart to barely watchable.

The Cannon Group

#92. King Solomon's Mines (1985)

- Director: J. Lee Thompson
- Stacker score: 44.0
- IMDb user rating: 5.2
- Metascore: 29
- Runtime: 100 minutes

Richard Chamberlain plays an explorer who has been hired by a beautiful young woman (Sharon Stone) to help her find her father, an archaeologist who has been kidnapped for his extensive knowledge of the fabled King Solomon's mines. An adaptation of the classic Victorian novel of the same name, the film takes a much lighter, wackier approach than any of its predecessors in an attempt to capture the same audiences that loved "Indiana Jones." Unfortunately, these efforts didn't pay off, and audiences dubbed the movie laughable and unconvincing.

Universal Pictures

#91. Head Over Heels (2001)

- Director: Mark Waters
- Stacker score: 44.0
- IMDb user rating: 5.4
- Metascore: 27
- Runtime: 86 minutes

This is essentially "Rear Window" with a female lead who falls in love with the guy she thinks she's seen commit a murder. Freddie Prinze Jr. was way too bubbly to inject the necessary darkness into the alleged killer character, and critics wrote the film off as a disposable teen date movie. It brought in only $10.4 million at the domestic box office.

New Line Cinema

#90. The Bachelor (1999)

- Director: Gary Sinyor
- Stacker score: 44.0
- IMDb user rating: 5.0
- Metascore: 31
- Runtime: 101 minutes

A commitment-phobic man is forced to settle down if he wants to keep his massive inheritance in this 1999 flop. Chris O'Donnell stars as the eponymous bachelor, with Renée Zellweger as his tired-of-waiting girlfriend. Despite a handful of celebrity cameos (Brooke Shields, Jennifer Esposito, Mariah Carey in her big-screen debut), the movie was a commercial disappointment, barely breaking even and earning reviews like "cliched" and "generic."

Regency Enterprises

#89. First Daughter (2004)

- Director: Forest Whitaker
- Stacker score: 44.0
- IMDb user rating: 5.0
- Metascore: 31
- Runtime: 106 minutes

The daughter of the President of the United States (Katie Holmes) falls in love with her college RA who, unbeknownst to her, is an undercover secret service agent tasked with her protection. Critics made unfavorable comparisons to the conceptually similar (but slightly less awful) "Chasing Liberty" from the same year. They declared the picture too saccharine for viewers outside the tween girl demo. The movie grossed $10.6 million.

Universal Pictures

#88. The Perfect Man (2005)

- Director: Mark Rosman
- Stacker score: 44.0
- IMDb user rating: 5.4
- Metascore: 27
- Runtime: 100 minutes

Before "catfishing" came into the cultural lexicon, this movie showed viewers what it meant. Holly (Hilary Duff) is sick of dealing with the fallout of her mother's failed relationships, so she creates a fictional online persona to court her mom in the hopes it will raise her mom's standards in men. When her mother (Heather Locklear) becomes invested in the romance, Holly must produce a real man to fill the shoes of the virtual suitor she's created. Critics rolled their eyes at the overly sentimental dialogue and obvious pandering to the tween crowd. The picture grossed a disappointing $19.8 million.

Universal Pictures

#87. Because I Said So (2007)

- Director: Michael Lehmann
- Stacker score: 44.0
- IMDb user rating: 5.5
- Metascore: 26
- Runtime: 102 minutes

Diane Keaton, in what film critic Richard Roeper singled out as the worst performance of her career, plays a meddlesome mother intent on setting her daughter (Mandy Moore) up with Mr. Right. Panned as a cliché, sappy, superficial chick flick, the film was dumped in the typically undesirable early February release window of 2007. Even so, ticket sales around Valentine's Day were strong enough that the movie was marginally profitable, raking in $42.7 million domestically. In retrospect, it's difficult to know who to pity more, the lonely hearts who saw this one solo or the significant others who were dragged out for date night.

Panorama Films

#86. Zoolander 2 (2016)

- Director: Ben Stiller
- Stacker score: 44.0
- IMDb user rating: 4.7
- Metascore: 34
- Runtime: 101 minutes

The original "Zoolander" might be a cult classic, but its sequel will hardly attain the same status. From its ridiculous plotline (Derek and Hansel on a mission to track down a mysterious agent who's killing the world's pop stars) to its laundry list of recycled jokes, there's a lot to criticize in this long-awaited follow-up. Even the dozens of celebrity cameos it so proudly boasted couldn't save it from its own lack of charm, creativity, or bizarre pacing.

Fox 2000 Pictures

#85. Chasing Papi (2003)

- Director: Linda Mendoza
- Stacker score: 43.5
- IMDb user rating: 4.7
- Metascore: 33
- Runtime: 80 minutes

"Chasing Papi" is a rom-com that feels as if it were intended more to appease the male gaze than to entertain viewers with its story. Three beautiful women (Sofía Vergara, Roselyn Sanchez, and Jaci Velasquez) discover they're all dating the same cosmetics salesman and must decide between fighting to be his one true love or keeping the friendship that's begun to develop between the trio. There's nothing overtly offensive about the film, but its unoriginal plot line, bland humor, and focus on its characters' looks over their identities don't do much to recommend it either.

Fred Films

#84. Blithe Spirit (2020)

- Director: Edward Hall
- Stacker score: 43.5
- IMDb user rating: 5.4
- Metascore: 26
- Runtime: 99 minutes

Based on the classic Noël Coward play of the same name, "Blithe Spirit" is about a writer who, after a seance gone wrong, finds himself trapped in a love triangle with the spirit of his dead first wife and his very alive second wife. The British film had a star-studded cast—Dan Stevens, Isla Fisher, Leslie Mann, Judi Dench, Emilia Fox—but failed to capture the kooky spirit of its source material, leaving many viewers with the feeling that it was a missed opportunity rather than the roaring success they'd hoped it would be.

Sherwood Productions

#83. Blame It on Rio (1984)

- Director: Stanley Donen
- Stacker score: 43.5
- IMDb user rating: 5.8
- Metascore: 22
- Runtime: 100 minutes

An aging executive played by Michael Caine is surprised to find the attractive daughter of his best friend coming on to him during vacation. Caine churned out a lot of movies in the '80s, and this release is one of his least distinguished outings. It managed to double its budget in domestic returns of $18.6 million, even though critics found the script creepy in its endorsement of dirty-old-man behavior. The film has not aged well and probably wouldn't have a chance of being made today.

Mandeville Films

#82. Beverly Hills Chihuahua (2008)

- Director: Raja Gosnell
- Stacker score: 43.5
- IMDb user rating: 3.9
- Metascore: 41
- Runtime: 91 minutes

A rom-com for the younger set, this Disney classic follows a spoiled Chihuahua who, after being dognapped, must find her way back to her owner with the help of her new paramour. Drew Barrymore and George Lopez voice the besotted canines, while Jamie Lee Curtis and Piper Perabo step in as their human owners. The storyline and humor are no worse than in any other kid-friendly, animated film, but the cultural stereotypes blatantly employed by the filmmakers left many audience members walking away with a bad taste in their mouths.

Ethea Entertainment

#81. He's All That (2021)

- Director: Mark Waters
- Stacker score: 43.5
- IMDb user rating: 4.4
- Metascore: 36
- Runtime: 88 minutes

TikTok star Addison Rae leads the cast of this gender-swapped remake of the 1990s classic "She's All That." Critics' biggest complaint with the Netflix original is that it didn't do enough to switch up the storyline, leaving the film to feel uninspired and repetitive rather than new and fresh, a fact that was only compounded by Rae's flat performance. One particularly harsh reviewer declared the film "unwatchable for anyone over 11 years old."

Miramax

#80. View from the Top (2003)

- Director: Bruno Barreto
- Stacker score: 43.5
- IMDb user rating: 5.3
- Metascore: 27
- Runtime: 87 minutes

An aspiring stewardess (Gwyneth Paltrow) juggles grueling flight training with the romantic pursuit of a law student (Mark Ruffalo). Critics found the low stakes better suited to a straight-to-video release and criticized technical elements of the film, such as its editing, as amateurish. The release, initially scheduled for 2001, was pushed back two years in the wake of 9/11 to put some distance between the national tragedy and the film's subject matter. The film, which grossed $15.6 million domestically, never made back its production budget.

Gladden Entertainment

#79. Mannequin (1987)

- Director: Michael Gottlieb
- Stacker score: 43.5
- IMDb user rating: 5.9
- Metascore: 21
- Runtime: 90 minutes

Campy is perhaps the best word to describe this 1987 rom-com about an artist who falls in love with a mannequin that is inhabited by the spirit of a woman from Ancient Egypt. "Mannequin" did decently well commercially, pulling in $6 million over the course of its opening weekend, but critics hated it for its bizarre storyline and complete lack of humor. Roger Ebert gave the Kim Cattrall and Andrew McCarthy flick a measly half-star, declaring it "dead" with a wake that lasted one-and-a-half hours.

Columbia Pictures

#78. Saving Silverman (2001)

- Director: Dennis Dugan
- Stacker score: 43.5
- IMDb user rating: 5.8
- Metascore: 22
- Runtime: 90 minutes

When J.D. Silverman (Jack Black) gets engaged to a manipulative, controlling woman, his best friends from childhood (Jason Biggs, Steve Zahn) go to great lengths to keep him from walking down the aisle. With humor aimed squarely at teen boys—there are lots of crude sex jokes, bathroom-related gags, and gratuitous torture moments—the film failed to land with its intended audience. Earning $26 million worldwide, it only squeaked past its production budget at the box office and many of its reviews were filled with notes like "mean-spirited" and "a terrible waste of assets."

Touchstone Pictures

#77. When in Rome (2010)

- Director: Mark Steven Johnson
- Stacker score: 43.5
- IMDb user rating: 5.5
- Metascore: 25
- Runtime: 91 minutes

Top critics didn't care for the dullness and lack of depth in this Kristen Bell and Josh Duhamel-led Disney flick. Bell is a New Yorker who has given up on romance until she throws some "magic" coins into a fountain in Rome and finds herself with many strange suitors to choose from. Dax Shepard (Bell's off-camera husband), Will Arnett, and Jon Heder all throw their hats in the ring, and some viewers found it hard not to like Bell's performance, but ultimately, the film's over-reliance on clichés left critics wanting more.

Semtex Films

#76. Filth and Wisdom (2008)

- Director: Madonna
- Stacker score: 42.9
- IMDb user rating: 5.3
- Metascore: 26
- Runtime: 84 minutes

Madonna's directorial debut, "Filth and Wisdom" was widely panned as "dumb and tacky." The comedy-drama follows three flatmates who spend their days toiling away in dead-end jobs (including ones in the sex work industry) while dreaming of bigger things. An incoherent and amateur effort, the movie premiered at the Berlin Film Festival before its limited theater run, where it earned just over $22,000 domestically.

Blue Angel Film

#75. Miss Conception (2008)

- Director: Eric Styles
- Stacker score: 42.9
- IMDb user rating: 4.6
- Metascore: 33
- Runtime: 104 minutes

In this bizarre 2008 release, Heather Graham plays a 30-something woman who discovers she has just one month left to get pregnant. When her boyfriend is unwilling to father her child, she embarks on a desperate quest to find a co-parent. A misconceived attempt to capitalize on the baby craze of the late '00s, the film feels outdated and cloddish and wound up only earning $2,134 at the domestic box office.

Absolute Entertainment (II)

#74. Molly (1999)

- Director: John Duigan
- Stacker score: 42.9
- IMDb user rating: 5.8
- Metascore: 21
- Runtime: 102 minutes

"Molly" is the type of movie that would almost certainly be boycotted by thoughtful moviegoers everywhere if it were released today. It follows a young autistic woman who finds herself living with her older bachelor brother after the institution she had been raised in unexpectedly shuts down. With both parties ill-prepared for this transition, they agree to an experiment that will make Molly more "normal," and chaos proceeds from there. Cliché, offensive at times, and poorly acted, the film only brought in $17,000 at the box office and remains one of the biggest misses of Elisabeth Shue's career.

Capital Arts Entertainment

#73. The Perfect Holiday (2007)

- Director: Lance Rivera
- Stacker score: 42.9
- IMDb user rating: 4.7
- Metascore: 32
- Runtime: 96 minutes

Gabrielle Union, playing a single mom, and Morris Chestnut, playing an aspiring musician, fall in love with the help of two Christmas angels (Queen Latifah and Terrence Howard) in this holiday-themed flop. Critics argued that the family-friendly story was too packed with clichés, pointless drama, and mediocre humor to be worth watching and pointed them elsewhere, leaving the film to earn only $5.8 million at the box office.

New Line Cinema

#72. Town & Country (2001)

- Director: Peter Chelsom
- Stacker score: 42.9
- IMDb user rating: 4.5
- Metascore: 34
- Runtime: 104 minutes

One of the biggest flops in movie history, "Town & Country" only earned $10 million against its $90 million budget. The film—which stars Warren Beatty, Diane Keaton, Goldie Hawn, and Garry Shandling—follows two aging couples who see their marriages tested by various infidelities. After spending three years in production (filming began in 1998 and didn't wrap until 2000), the finished product felt disjointed and choppy thanks to its dozens of rewrites and re-shoots, a fact that critics and audiences alike were quick to pick up on.

New Regency Pictures

#71. Simply Irresistible (1999)

- Director: Mark Tarlov
- Stacker score: 42.9
- IMDb user rating: 5.2
- Metascore: 27
- Runtime: 96 minutes

Sarah Michelle Gellar stars as an heiress to a restaurant who is blessed with magical cooking and seduction abilities by a crab in a tuxedo. The title begs for oppositional review bylines, which critics were eager to deliver given that the plot never rises above its absurd premise. Domestic grosses of $4.4 million reflected a disconnected marketing campaign. A somewhat ominous movie poster featured Gellar pouting in front of a full moon, a tableau that was perhaps attempting to recall her iconic TV role in "Buffy The Vampire Slayer" but wasn't in the least bit reflective of the film's goofy tone.

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Walt Disney Pictures

#70. Confessions of a Teenage Drama Queen (2004)

- Director: Sara Sugarman
- Stacker score: 42.9
- IMDb user rating: 4.6
- Metascore: 33
- Runtime: 89 minutes

Lindsay Lohan and Megan Fox star as high school rivals in this classic teenage comedy. Many of the film's detractors cited its predictable hijinks, juvenile acting, and cliché plot points as reasons for labeling it unwatchable fluff, but its intended audience didn't seem to mind those things, buying enough tickets to earn it a respectable $33.3 million at the worldwide box office.

Innis Lake Entertainment

#69. No Stranger Than Love (2015)

- Director: Nick Wernham
- Stacker score: 42.4
- IMDb user rating: 4.9
- Metascore: 29
- Runtime: 89 minutes

IndieWire wrote that "No Stranger Than Love," a film about a woman who loses her beau to a mysterious pit that opens up in the middle of her living room, "has a hole where its heart should be." Alison Brie plays art teacher Lucy, a woman who every man in town is seemingly in love with, and her performance is the only redeemable aspect of this poorly paced rom-com. Ultimately, the surreal components of the story are introduced far too late in the run time for this plotline to really gel.

Universal Pictures

#68. Stroker Ace (1983)

- Director: Hal Needham
- Stacker score: 42.4
- IMDb user rating: 4.8
- Metascore: 30
- Runtime: 96 minutes

Burt Reynolds, once one of Hollywood's biggest heartthrobs and most sought-after actors, blamed "Stroker Ace" for the demise of his career. The film, which sees Reynolds play a NASCAR driver who is at odds with his fried-chicken sponsor and desperate to seduce his new public relations manager, was a massive flop upon its release. The New York Times called it "the must-miss movie of the summer," and critics complained that it was too boring and uninspired to merit even a single viewing.

New Line Cinema

#67. New Year's Eve (2011)

- Director: Garry Marshall
- Stacker score: 42.4
- IMDb user rating: 5.6
- Metascore: 22
- Runtime: 118 minutes

This 2011 schlock-fest features an ensemble cast including Jessica Biel, Halle Berry, Michelle Pfeiffer, Abigail Breslin, Robert De Niro, and Josh Duhamel in a tale of intertwining love stories set on Dec. 31 in Manhattan. This was an obvious retread of "Love Actually," but bereft of that film's heart or humor, and critics saw straight through the producers' cynicism, warning audiences to seek other holiday options. Domestic gross was $54.5 million, a poor showing for such a star-studded picture.

Fox 2000 Pictures

#66. Bride Wars (2009)

- Director: Gary Winick
- Stacker score: 42.4
- IMDb user rating: 5.4
- Metascore: 24
- Runtime: 89 minutes

Two best friends (Kate Hudson and Anne Hathaway) become engaged in a bridezilla showdown when, due to a clerical error, they accidentally schedule their weddings on the same day. This 2009 movie drew plenty of ire from critics who, fed up with the overdone wedding movie genre, pounced on the film's superficiality and disdain for its audience. Said audience showed up anyway, netting the picture a profitable $115 million worldwide.

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Unity Productions

#65. Private School (1983)

- Director: Noel Black
- Stacker score: 41.8
- IMDb user rating: 5.2
- Metascore: 25
- Runtime: 89 minutes

"Private School" has a threadbare plot and seems to only exist as a vehicle for the writers' crude and derogatory sex jokes. Ostensibly, the film, which was targeted at teens, is about a young couple seeking to lose their virginities to one another. In reality, however, it feels like an awkward 80-minute stand-up set, replete with plenty of nude shots, full of content that Roger Ebert dubbed "anti-woman." It's no surprise that women (the primary audience from rom-coms) haven't flocked to this one in the 40 years since its release.

Warner Bros.

#64. License to Wed (2007)

- Director: Ken Kwapis
- Stacker score: 41.8
- IMDb user rating: 5.2
- Metascore: 25
- Runtime: 91 minutes

A reverend (Robin Williams) puts an engaged couple through the wringer in his grueling marriage preparation course. John Krasinski of the American version of "The Office" plays the aspiring groom alongside Mandy Moore as his would-be bride. Williams' performance was phoned in, and the script is predictable and unfunny. The film saw a domestic gross of $43.8 million.

Columbia Pictures

#63. The Bounty Hunter (2010)

- Director: Andy Tennant
- Stacker score: 41.8
- IMDb user rating: 5.5
- Metascore: 22
- Runtime: 110 minutes

The plot of this 2010 film is a grab bag of recycled concepts: A bounty hunter (Gerard Butler) is tasked with bringing in his bail-skipping ex-wife (Jennifer Aniston) but instead finds himself caught up in her attempt to solve a high-profile murder. Critics dismissed the film as assembly-line Hollywood product and snubbed the phoned-in performances. Even so, the film made $67.1 million at domestic box offices, turning a profit.

J2 Pictures

#62. An Invisible Sign (2010)

- Director: Marilyn Agrelo
- Stacker score: 41.3
- IMDb user rating: 5.3
- Metascore: 23
- Runtime: 96 minutes

Unlike poetry or art, math isn't generally a subject that incites feelings of love or romance, so it seems an odd theme to center a rom-com around. Still, the producers of "An Invisible Sign" decided to try it anyways with this movie about a woman (Jessica Alba) who uses her passion for math to reconnect with life and possible love interests after her father's sudden illness. Reviewers called the film boring and uneven, a failed attempt to marry logic with love.

Davis Entertainment

#61. A Little Bit of Heaven (2011)

- Director: Nicole Kassell
- Stacker score: 41.3
- IMDb user rating: 6.2
- Metascore: 14
- Runtime: 106 minutes

"A Little Bit of Heaven," a dramatic tear-jerker about a woman who finds love for the first time right after being diagnosed with terminal cancer, would fit right in with the stories in Nicholas Sparks' back catalog. But unlike Sparks-based movies, which are generally well-received by die-hard rom-com watchers, this film suffered from a lack of chemistry between its main actors (Kate Hudson and Gael García Bernal), odd tone discrepancies, and an oversentimental perspective on life, sexuality, and love. It was so bad—only earning just over $15,000 at the domestic box office—that reviewers dubbed it "a little bit of hell."

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Columbia Pictures

#60. Did You Hear About the Morgans? (2009)

- Director: Marc Lawrence
- Stacker score: 41.3
- IMDb user rating: 4.9
- Metascore: 27
- Runtime: 103 minutes

A Manhattan alpha couple gets a second chance to repair their flailing marriage when they're relocated to a tiny town in Wyoming through witness relocation. (Yes, it's a plot that sounds like the kind of movie you might see parodied in a Judd Apatow comedy.) Critics acknowledged moments of on-screen charm between leads Hugh Grant and Sarah Jessica Parker, but overall consensus was that the movie was cynical studio dreck. The domestic gross of $29.6 million was nothing to write home about, but the film performed well overseas and brought in a total of $85.3 million internationally.

A Happy Place

#59. On the Line (2001)

- Director: Eric Bross
- Stacker score: 40.8
- IMDb user rating: 4.1
- Metascore: 34
- Runtime: 85 minutes

A weak "Serendipity" rework starring an 'N Sync heartthrob, "On the Line" follows a shy advertising executive as he searches for a woman he had a chance encounter with on Chicago's L train system. Lance Bass takes the lead, with Emmanuelle Chriqui playing his soulmate, and Joey Fatone playing one of his many roommates. The film's unbelievable plotline failed to entice its intended teenage audience to part with its hard-earned money, leaving it to earn just over $4.4 million at worldwide box offices, despite a $16 million budget.

Gladden Entertainment

#58. Mannequin: On the Move (1991)

- Director: Stewart Raffill
- Stacker score: 40.8
- IMDb user rating: 4.4
- Metascore: 31
- Runtime: 95 minutes

Why producers felt that making a sequel to a film as awful as the original "Mannequin" would be a good idea is unclear, but make one they did. In the follow-up, a young department store employee (William Ragsdale) falls in love with a wooden mannequin (Kristy Swanson), who is actually a medieval peasant woman that has fallen under a 1,000-year curse. The Los Angeles Times called the film "insipid to the extreme," and seemingly no one was impressed by its recycled plot points, tired jokes, and oddly frantic pacing.

The Guber-Peters Company

#57. Who's That Girl (1987)

- Director: James Foley
- Stacker score: 40.8
- IMDb user rating: 4.8
- Metascore: 27
- Runtime: 92 minutes

Madonna has tried to launch her film career multiple times with very little success. "Who's That Girl" is yet another of the pop star's early attempts to establish herself as a serious actress. In the film, she plays a street-smart woman who has been falsely accused of murdering her boyfriend. After being released from prison, she convinces the uptight lawyer tasked with getting her back to her hometown to help her prove her innocence. Along the way, they fall in love. Madonna's horrible overacting and the film's clumsy jokes led critics to universally pan it following its 1987 release.

Columbia Pictures

#56. Whatever It Takes (2000)

- Director: David Raynr
- Stacker score: 40.8
- IMDb user rating: 5.5
- Metascore: 20
- Runtime: 94 minutes

A young James Franco and Shane West couldn't save this teen update of the classic Cyrano de Bergerac tale, in which nerdy West falls for the cute, popular girl in school, and Franco looks for help from West to get the attention of his best friend and fellow nerdy pal, Maggie (Marla Sokoloff). Critics panned it, and the movie was a commercial flop, bringing in only $8.7 million at domestic box offices, well below its $32 million budget.

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Lionsgate

#55. Good Luck Chuck (2007)

- Director: Mark Helfrich
- Stacker score: 40.8
- IMDb user rating: 5.6
- Metascore: 19
- Runtime: 96 minutes

This film gave a lot of ammunition to members of the "Dane Cook isn't funny" bandwagon. The premise is actually chuckle-worthy: A serial dater who was hexed by a goth girl into perpetual singledom as a 10-year-old must try to make an adult relationship with a sexy penguin specialist work. Unfortunately, due to the lack of comedic chops in the cast, the movie was slammed by critics and by countless road comics who, jealous of Cook's stardom, slagged it off in clubs around the country. Cook's fan base showed up anyway, and the film raked in $35 million in domestic box offices to turn a profit.

Lionsgate

#54. Killers (2010)

- Director: Robert Luketic
- Stacker score: 40.8
- IMDb user rating: 5.4
- Metascore: 21
- Runtime: 100 minutes

Katherine Heigl plays a newlywed who discovers her husband (Ashton Kutcher) is an assassin, a revelation that throws their marriage into turmoil. This "Mr. & Mrs. Smith" lite turned off critics with its warmed-over plot and plain dullness. The picture made $47 million at domestic box offices, a figure dwarfed by the conceptually similar Tom Cruise/Cameron Diaz double-header "Knight and Day," which was released in the same month and proved a big commercial hit.

Open Road Films (II)

#53. Mother's Day (2016)

- Director: Garry Marshall
- Stacker score: 40.2
- IMDb user rating: 5.6
- Metascore: 18
- Runtime: 118 minutes

In the same vein as "Valentine's Day" and "New Year's Eve," "Mother's Day" follows a group of seemingly unconnected people as they set out to celebrate their moms. Directed by Gary Marshall (his last film before his death in July 2016), the movie boasts a star-studded ensemble cast including names like Julia Roberts, Jennifer Aniston, Kate Hudson, Jason Sudeikis, Timothy Olyphant, and Jon Lovitz. Poorly written, with overpacked plot lines and jokes that verge on racist, the movie was a miss for both audiences and critics alike.

Touchstone Pictures

#52. Cabin Boy (1994)

- Director: Adam Resnick
- Stacker score: 39.7
- IMDb user rating: 5.2
- Metascore: 21
- Runtime: 80 minutes

When a movie's main character is described by critics who enjoyed it as unpleasant, despicable, and loathsome, it's hard to imagine that it's going to find a wide audience. That was certainly the case with "Cabin Boy," a fantasy comedy story by "Late Night with David Letterman" writers Chris Elliott and Adam Resnick. Even the film's original slapstick and sight gags weren't enough to redeem the bizarre tale of a privileged prep-school graduate who finds himself working (and falling in love) aboard a fishing boat with a … well … "filthy" name.

Eddie Murphy Productions

#51. Vampire in Brooklyn (1995)

- Director: Wes Craven
- Stacker score: 39.7
- IMDb user rating: 4.6
- Metascore: 27
- Runtime: 100 minutes

Comedy-horror rarely works as a mashup. For every "American Werewolf in London," there are dozens of misfires that fail to balance the competing requirements of the two genres. This is one of those. Eddie Murphy plays a vampire named Maximillian, who tries to seduce a detective while sabotaging the romantic advances of her longtime partner. Horror veteran Wes Craven directed but failed to provide any real scares. Critic Roger Ebert wrote of the film: "To call this a comedy is a sign of optimism; to call it a comeback for Murphy is a sign of blind faith." Audiences were at least curious enough that the film pulled in a haul just shy of $19.8 million, but it was poorly regarded and has not stood the test of time.

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DreamWorks

#50. Surviving Christmas (2004)

- Director: Mike Mitchell
- Stacker score: 39.7
- IMDb user rating: 5.4
- Metascore: 19
- Runtime: 91 minutes

In a plot that calls for way too much suspension of disbelief from the outset, a wealthy but alienated ad exec (Ben Affleck) bribes a family (with a dad played by James Gandolfini) to pose as his own so that he doesn't have to spend Christmas alone. The story pivots when the family's eldest daughter (Christina Applegate) arrives late and throws a new romantic wrench into his fantasy. Predictable and humorless complications ensue. Amazingly, the WGA lists four screenwriters for this trainwreck. An $11.7 million domestic box office sale made for a disappointing holiday haul.

Joseph Hamilton International Productions

#49. The Pirate Movie (1982)

- Director: Ken Annakin
- Stacker score: 39.1
- IMDb user rating: 5.3
- Metascore: 19
- Runtime: 98 minutes

The vast majority of "The Pirate Movie" happens in a dream sequence, a twist that turns many viewers off to even the best stories. Unfortunately, the film also lacked a solid plot—it follows a couple who meet at a pirate festival in Australia and who turn out to have also been pirates in a past life—the musical rom-com had two strikes against it before it even hit theaters. Its third strike came when viewers realized it was a thinly veiled knockoff of the play "The Pirates of Penzance," something the marketing hadn't been clear about.

New Line Cinema

#48. Sex and the City 2 (2010)

- Director: Michael Patrick King
- Stacker score: 39.1
- IMDb user rating: 4.5
- Metascore: 27
- Runtime: 146 minutes

The critics who were lukewarm on the first big-screen adaptation of the hit HBO show really sank their teeth into its sequel. And at a running time of almost two-and-a-half hours, the film served up plenty of fodder for their criticisms. Most reviewers agreed that Carrie (Sarah Jessica Parker) and her crew of Manolo-heeled NYC gal pals had long overstayed their welcome and warned that only diehard fans need consider lining up for this pointless and thinly plotted coda to their saga. It still made a boatload—$290.7 million worldwide—but by this point, the loft salary requirements of its stars had produced a budget that exceeded its return.

Cinejota Filmproduktionsgesellschaft mbH & Co.

#47. Undiscovered (2005)

- Director: Meiert Avis
- Stacker score: 38.6
- IMDb user rating: 4.2
- Metascore: 29
- Runtime: 97 minutes

Four aspiring performers try to get their careers off the ground in this 2005 drama. The basic story is one that has been told time and time again, and "Undiscovered" had nothing new to offer to the conversation, nor did it tap into the emotions of its audience in any real way. Despite its enticing preview and interesting casting choices (Ashlee Simpson's first big screen role), the movie set a record for second-weekend drop-offs, with an 86.4% decrease in ticket sales.

Morgan Creek Entertainment

#46. Juwanna Mann (2002)

- Director: Jesse Vaughan
- Stacker score: 38.6
- IMDb user rating: 4.7
- Metascore: 24
- Runtime: 91 minutes

An urban spin on a "Tootsie"-style gender-switch plot, "Juwanna Mann" stars longtime character actor Miguel A. Núñez Jr. in his first and last leading role. The story's about a hot-tempered basketball player who gets booted from the league and decides to don some fake breasts and eyelashes to try his luck on the women's side of the game. He lands a spot on a team, but his plan gets thrown into turmoil when he starts to fall for a no-nonsense coach, played by Vivica A. Fox. Critics found it simplistic and unoriginal, and its $13.57 million domestic box office haul didn't cover its production budget. Nevertheless, in a 2015 TMZ interview, Núñez claimed a Juwanna Mann sequel was in the works, but IMDb provides no corroboration for this claim.

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New Line Cinema

#45. Even Cowgirls Get the Blues (1993)

- Director: Gus Van Sant
- Stacker score: 38.6
- IMDb user rating: 4.3
- Metascore: 28
- Runtime: 106 minutes

This film, based on a beloved Tom Robbins novel with strong feminist themes, was supposed to be indie director Gus Van Sant's triumphant follow-up to "My Own Private Idaho." It's a movie with a lot of intriguing ingredients: Uma Thurman stars as a woman who uses her unusually large thumbs to hitchhike her way across the country, winding up at a ranch staffed by cowgirls. There she has a love affair with the ranch's leader, played by Rain Phoenix (sister to Joaquin and River Phoenix). Despite the caliber of the source material and edgy (for 1993) exploration of gay themes, critics found little value in the finished product. Van Sant had no feel for the subject matter and drew out confusing and sometimes embarrassing performances from his actors. Box office receipts fell shy of $2 million.

Lakeshore Entertainment

#44. The Next Best Thing (2000)

- Director: John Schlesinger
- Stacker score: 38.6
- IMDb user rating: 4.6
- Metascore: 25
- Runtime: 108 minutes

Madonna and Rupert Everett star in this comedy about a straight woman and a gay man who decide to conceive and raise a child together. Critics found the delivery heavy-handed and the tear-jerker moments forced. The $15 million domestic box office receipts did little to convince producers that Madonna was a bankable star outside the music business.

Twentieth Century Fox

#43. Say It Isn't So (2001)

- Director: J.B. Rogers
- Stacker score: 38.6
- IMDb user rating: 5.0
- Metascore: 21
- Runtime: 95 minutes

The Farrelly Brothers produced this 2001 romantic comedy, directed by J.B. Rogers, who had previously worked with them as a first assistant director. Gilly (Chris Klein) and Jo (Heather Graham) are enjoying a passionate love affair when they find out they're actually brother and sister and have to break things off in a hurry. But when he finds out their supposed blood relation is a lie perpetuated by a meddling third party, Gilly must rush to stop Jo's marriage to "the wrong guy." The incest humor creeped out critics and audiences, and overall, the movie lacked the charm, humor, and originality of the brothers' earlier sleeper hit "There's Something About Mary." The box office total was $12.3 million, with a $25 million production budget.

Warner Bros.

#42. Summer Catch (2001)

- Director: Michael Tollin
- Stacker score: 38.6
- IMDb user rating: 5.0
- Metascore: 21
- Runtime: 104 minutes

Another Freddie Prinze Jr. rom-com, this time pairing the actor up with Jessica Biel. The story, a classic "Lady and the Tramp" setup, has Prinze Jr.'s blue-collar baseball player character falling for an unattainable upper-crust girl with a controlling father. The critics' consensus was that there wasn't enough baseball for a baseball movie and that the romance lacked sufficient flavor or complication to draw interest. Worldwide box office receipts were a just below $20 million.

FTM Productions

#41. Serving Sara (2002)

- Director: Reginald Hudlin
- Stacker score: 38.6
- IMDb user rating: 5.3
- Metascore: 18
- Runtime: 99 minutes

Joe, played by Matthew Perry, gets more than he bargained for when he's tasked with serving divorce papers to the elusive Sara (Elizabeth Hurley). The typical romantic comedy plot plays out, and opposites end up attracting without much regard for originality or humor. As bland as this movie is, the off-screen events surrounding its production made for juicy tabloid fodder. Perry landed in rehab for painkiller addiction during production, and later Hurley's boyfriend accused Perry of impregnating her (a claim was later discredited through blood tests). If only the script had been as intriguing.

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Touchstone Pictures

#40. Cocktail (1988)

- Director: Roger Donaldson
- Stacker score: 38.6
- IMDb user rating: 5.9
- Metascore: 12
- Runtime: 104 minutes

"Cocktail" is one of those rare films that was a huge failure with critics but a massive hit with audiences. It follows a business school student in NYC who turns to bartending in order to fund his education. After a falling out with his mentor, he flees to Jamaica, where he falls in love and learns some hard life lessons. Critics argued that the film was shallow and vapid, with little to say about either love or materialism, but fans disagreed, flocking in the thousands to see Tom Cruise in action and earning the film $78.2 million at the box office.

Electric Eye Entertainment Corporation

#39. Delgo (2008)

- Directors: Marc F. Adler, Jason Maurer
- Stacker score: 38.0
- IMDb user rating: 4.3
- Metascore: 27
- Runtime: 94 minutes

The first computer-animated movie to make our list, "Delgo" is a fantasy film aimed at adult audiences. A "Romeo and Juliet" story about two young beings from enemy alien races who fall in love, the film utilized the voices of Freddie Prinze Jr. and Jennifer Love Hewitt to bring its main characters to life. Audiences complained that the story felt like a mashup of elements from existing fantasy tales and that the dull voice acting did little to bring any of those pieces to life. Unsurprisingly, the film bombed at the box office, earning just over $500,000 on its opening weekend, which Yahoo! Movies (via SlashFilm) explained meant that an average of just two people attended each showing.

2DS Productions

#38. Bad Johnson (2014)

- Director: Huck Botko
- Stacker score: 38.0
- IMDb user rating: 4.5
- Metascore: 25
- Runtime: 88 minutes

When a womanizer realizes his wish for his penis to leave him alone has come true after it falls off and takes on human form, he must figure out how to be a "real man" without his manhood. The plot of "Bad Johnson" is so thin it would have been better suited as a four-minute SNL skit than a full-length feature film. To flesh out the lackluster story, writers padded the movie with cringey jokes and eye-rolling sex metaphors, which only left audiences wholly disappointed in the project and desperate for something of substance to cling to.

TriStar Pictures

#37. Look Who's Talking Now (1993)

- Director: Tom Ropelewski
- Stacker score: 38.0
- IMDb user rating: 4.4
- Metascore: 26
- Runtime: 96 minutes

By now, we've probably all seen those Twitter threads about what would happen if AI were put in charge of writing our movies and novels. "Look Who's Talking Now" is probably the closest thing we currently have to an answer—an incongruent assortment of plotlines and thoughts that only vaguely resemble a story. John Travolta and Kirstie Alley reprise their role as the Ubriacco parents, only this time it's not their infants who are talking but their dogs, who are voiced by Danny DeVito and Diane Keaton. Audiences hated the movie just as much as critics did, and the finale of the "Look Who's Talking" series only netted $10.3 million at the box office against its $20 million-plus production budget.

Photo 12 / Alamy Stock Photo

#36. Lost & Found (1999)

- Director: Jeff Pollack
- Stacker score: 37.5
- IMDb user rating: 5.0
- Metascore: 19
- Runtime: 100 minutes

David Spade plays a restaurateur who steals a woman's dog in the hopes of returning it to impress her, but his plan to win her affection backfires. The thin premise is good for about 15 minutes of comedy before the film devolves into meanness, stupidity, and ripping off jokes from superior rom-coms such as "There's Something About Mary." Spade, as co-writer of the script, was doubly implicated in this flop, which grossed only $6.5 million. The poster, in a self-aware nod to its leading man's public image as a weaselly lech, features the SNL veteran holding the stolen mutt in front of his crotch with the tagline: "One of these dogs must be Spade."

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MGM

#35. Van Wilder: The Rise of Taj (2006)

- Director: Mort Nathan
- Stacker score: 37.5
- IMDb user rating: 4.8
- Metascore: 21
- Runtime: 97 minutes

The first misstep "Van Wilder: The Rise of Taj" made was naming the film after a character that wasn't actually in it. A follow-up to the 2002 release "National Lampoon's Van Wilder," this film didn't actually center around Ryan Reynold's character but had a new lead in Kal Penn. The second misstep it made was not including a single original plot element, instead recycling storylines that have been used in a half-dozen "National Lampoon" films previously. Between mishandling fan expectations and underdelivering in terms of content, it's not surprising that this ranks as one of the worst rom-coms of all time.

Yari Film Group (YFG)

#34. The Accidental Husband (2008)

- Director: Griffin Dunne
- Stacker score: 37.5
- IMDb user rating: 5.5
- Metascore: 14
- Runtime: 90 minutes

A talented cast—including Uma Thurman, Jeffrey Dean Morgan, Colin Firth, Sam Shephard, and Isabella Rossellini—is wasted on this lifeless rom-com. A radio talk show host (Thurman) who advises a woman to break off her engagement must then contend with reprisal from the woman's jilted fiance (Dean Morgan). In a tried-and-true application of the well-worn formula, the two leads proceed to bicker their way to a love connection. It's in-flight movie caliber stuff at best, although perhaps more entertaining if you pretend Jeffrey Dean Morgan is playing a pre-zombie apocalypse version of his Negan character from "The Walking Dead."

PalmStar Media

#33. Some Kind of Beautiful (2014)

- Director: Tom Vaughan
- Stacker score: 37.0
- IMDb user rating: 5.7
- Metascore: 11
- Runtime: 99 minutes

Not a single character in "Some Kind of Beautiful" seems to have their head on straight. From the professor who regularly sleeps with his students (Pierce Brosnan), to the American exchange student (Jessica Alba) who willingly puts herself in a position to become pregnant with a child she doesn't seem to want, to the much-older stepsister (Salma Hayek) who falls in love with her younger sister's husband, all of the movie's characters spend the entire run time making awful choices. Even the producers seemed to know how big of a flop they had on their hands and chose to only release the film into a handful of theaters before sending it straight to on-demand.

DreamWorks

#32. Norbit (2007)

- Director: Brian Robbins
- Stacker score: 37.0
- IMDb user rating: 4.1
- Metascore: 27
- Runtime: 102 minutes

Eddie Murphy had an epic run of bad movies in the 2000s, and "Norbit" is perhaps the worst of the bunch. The conflict of the story centers on the title character trying to flee a bad marriage for greener romantic pastures. But his path to freedom requires standing up to his abusive, obnoxious spouse, also played by Murphy. As if the offensive fat-suit humor wasn't enough tastelessness for one film, Murphy also managed to jam in some cringeworthy racial humor in his third performance in the film as Mr. Wong, a walking Asian stereotype who displays blatant prejudice throughout the film. "Norbit" grossed over $95 million domestically, proving there's no accounting for (bad) taste.

Align

#31. Die in a Gunfight (2021)

- Director: Collin Schiffli
- Stacker score: 36.4
- IMDb user rating: 4.4
- Metascore: 23
- Runtime: 92 minutes

Pitched as an updated version of the "Romeo and Juliet" story, "Die in a Gunfight" follows two troubled kids as they form a relationship against the wishes of their respective families. The movie desperately wanted to be seen as edgy but, with the exception of several bloody scenes, didn't wind up doing anything groundbreaking with its source material. In fact, it fell so flat that ScreenRant called it "utterly empty, with poorly developed characters, clunky dialogue, and a disingenuous romance that attempts to be epic in nature."

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Columbia Pictures

#30. Spring Break (1983)

- Director: Sean S. Cunningham
- Stacker score: 35.9
- IMDb user rating: 4.9
- Metascore: 17
- Runtime: 102 minutes

Four guys—two nerds and two popular kids—wind up spending their spring break together, cavorting around Fort Lauderdale and trying to dodge an enraged father and a developer with an agenda. The plot is predictable, the writers' treatment of women and minorities despicable, and the jokes drier than they have any right to be. Despite its obvious negative, the movie somehow managed to bring in a mediocre $24 million at the box office.

Paramount Pictures

#29. The Honeymooners (2005)

- Director: John Schultz
- Stacker score: 35.3
- IMDb user rating: 3.4
- Metascore: 31
- Runtime: 90 minutes

A remake of the classic TV series, "The Honeymooners" stars Cedric the Entertainer and Mike Epps as working-class friends whose lives are anchored by their long-suffering wives (Gabrielle Union and Regina Hall). The problem with the film is that it takes sitcom elements and tries to jam them into a feature-length film. The result, despite the four writers' best efforts, simply didn't work, and audiences felt that the movie wasn't memorable, interesting, or entertaining.

Abbolita Productions

#28. Yoga Hosers (2016)

- Director: Kevin Smith
- Stacker score: 35.3
- IMDb user rating: 4.2
- Metascore: 23
- Runtime: 88 minutes

Often referred to as the lowest point of Kevin Smith's career, "Yoga Hosers" is a comedy spinoff of his 2014 horror film "Tusk." Starring Harley Quinn Smith and Lily-Rose Depp (the only bright spots in the entire mess), it follows two teenage convenience store clerks who are forced to kill their crushes in self-defense after realizing the boys are part of a Satanist cult. The movie is a grab bag of plot lines and tropes and feels more like the unhinged ramblings of the director than a cohesive story, intentionally told.

Alliance Atlantis Communications

#27. Slackers (2002)

- Director: Dewey Nicks
- Stacker score: 35.3
- IMDb user rating: 5.3
- Metascore: 12
- Runtime: 86 minutes

No relation to Richard Linklater's pioneering 1991 mumblecore flick "Slacker," this 2002 college comedy failed to rise above the glut of early 2000s teen gross-out fare. A geeky Jason Schwartzman blackmails a scheming Devon Sawa (and his two buddies) into setting him up with the girl he's obsessed with. Sawa's character falls for the girl in question (played by Jaime King), and hijinks ensue. This film was the product of the ill-fated Destination Films, a low-budget film company acquired by Sony Pictures Entertainment in 2001. Sony let this one sit on a shelf for a year before releasing it through their Screen Gems arm. A gem it was not, and it grossed $6.4 million against a $14 million production budget.

Fox 2000 Pictures

#26. All About Steve (2009)

- Director: Phil Traill
- Stacker score: 35.3
- IMDb user rating: 4.8
- Metascore: 17
- Runtime: 99 minutes

Sandra Bullock plays against type in this quirky comedy about a kooky puzzle maker who begins stalking a cameraman played by Bradley Cooper. The usually charming Bullock delivers a performance creepier than was perhaps intended, and critics lambasted the film for its odd, off-putting tone and unlikeable heroin. Nevertheless, the star power of the cast attracted a large enough audience that the film grossed over $40 million worldwide, more than doubling its production budget. Bullock famously attended the Razzie Awards ceremony and handed out copies of the movie to the audience after they awarded her Worst Actress for her performance in the film.

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IFC Films

#25. I Hate Valentine's Day (2009)

- Director: Nia Vardalos
- Stacker score: 34.8
- IMDb user rating: 4.7
- Metascore: 17
- Runtime: 98 minutes

IFC Films attempted to capitalize on the runaway success of "My Big Fat Greek Wedding" by re-teaming its co-stars Nia Vardalos and John Corbett for this 2009 rom-com. The concept and story are totally boilerplate: A woman with a "five-date max" rule is forced to reconsider when she meets a guy worth going the distance for. Critics thought the dating, as portrayed, was outdated and, at best, considered it a cheap guilty pleasure. Audiences barely noticed it: Domestic gross was at $11,004.

Mad Chance

#24. Behaving Badly (2014)

- Director: Tim Garrick
- Stacker score: 33.7
- IMDb user rating: 4.4
- Metascore: 18
- Runtime: 97 minutes

Tim Garrick confused irony and cynicism for comedy in the nihilistic teen flick "Behaving Badly." When a high schooler (Nat Wolff) discovers that his longtime crush (Selena Gomez) is finally single, he makes a bet with the local mobster's son (Nate Hartley) that he'll be able to sleep with her before the week is out. What follows is a chain of disasters and morally questionable events that supposedly lead to Wolff's character learning what it means to have a moral compass. Audiences felt that the film painted female sexuality as a black-and-white matter (i.e., sexually active equals bad, sexually pure equals good), which didn't ring true to them or entice them to buy tickets to the flop of a project.

Unified Pictures

#23. The Layover (2017)

- Director: William H. Macy
- Stacker score: 33.7
- IMDb user rating: 4.7
- Metascore: 15
- Runtime: 88 minutes

"The Layover" may call itself a romantic comedy, but at its heart, it's an attack on female friendship. When two women (Kate Upton and Alexandra Daddario) fall for the same guy (Matt Bar) while on vacation, they're prepared to throw away decades of friendship for an opportunity to sleep with him. The film definitely wouldn't pass the Bechdel Test, and audiences and critics alike were bored by its well-trodden subject matter.

Open City Films

#22. Down to You (2000)

- Director: Kris Isacsson
- Stacker score: 33.7
- IMDb user rating: 4.9
- Metascore: 13
- Runtime: 91 minutes

In an attempt at a teen version of "Annie Hall," this movie starred then-faves Freddie Prinze Jr. and Julia Stiles as a pair of teenagers struggling to navigate the trials and tribulations of young love in the Big Apple. An aimless story, adolescent dialogue, and lack of on-screen romantic chemistry drew a tepid response from critics, and the movie lost money for Miramax.

Dimension Films

#21. My Boss's Daughter (2003)

- Director: David Zucker
- Stacker score: 33.7
- IMDb user rating: 4.7
- Metascore: 15
- Runtime: 86 minutes

Ashton Kutcher plays a rookie executive who agrees to house-sit for his boss in the hopes of spending time with the man's attractive daughter (Tara Reid). Reviews declared the script crude and offensive. The film received three Razzie Award nominations, including Worst Actor (Ashton Kutcher), Worst Supporting Actress (Tara Reid), and Worst Screen Couple. The movie still managed to gross over $18.2 million worldwide, enough to cover its production budget and then some.

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Fuzzy Bunny Films (I)

#20. Crossroads (2002)

- Director: Tamra Davis
- Stacker score: 33.7
- IMDb user rating: 3.5
- Metascore: 27
- Runtime: 93 minutes

Three teenage girls set out on a cross-country road trip in this coming-of-age film written by none other than Shonda Rhimes. While the storyline itself isn't all that bad, critics weren't excited by the final product, calling it "a cliched and silly pop star vanity project… for Britney Spears fans only."

Paramount Pictures

#19. The Love Guru (2008)

- Director: Marco Schnabel
- Stacker score: 33.7
- IMDb user rating: 3.8
- Metascore: 24
- Runtime: 87 minutes

Prior to helming this Mike Myers flop, director Marco Schnabel's career was in dire straits. After being fired early on during the making of the Will Ferrell soccer comedy "Kicking and Screaming," Schnabel was having a hard time convincing any studio executive to let him make another movie. So when he was tapped by Myers, who knew him from his second unit director stint on "Austin Powers in Goldmember," he leaped at the opportunity to get back behind the camera. Unfortunately, Myers' new character, a hippie-ish love guru tasked with healing the marriage of a hockey player, failed to resonate with audiences. The movie—cheesy, juvenile, and grating—fell $20 million shy of recouping its budget. It remains Schnabel's sole IMDb credit as a director.

K. JAM Media

#18. Accidental Love (2015)

- Director: David O. Russell
- Stacker score: 33.2
- IMDb user rating: 4.1
- Metascore: 20
- Runtime: 100 minutes

This is a weird one. The story's about Alice, a soon-to-be-wed waitress (played by Jessica Biel) who, through a freak accident, ends up with a nail lodged in her head. The injury produces bizarre and hypersexual behavior that leads to Alice's fiance calling off their marriage. She rebounds into the arms of a senator (Jake Gyllenhaal) who helps empower her campaign for people with bizarre injuries. The film was directed and co-written by five-time Oscar nominee David O. Russell, who was so ashamed of his work on the flick that he abandoned it in its final stages and opted to be credited with a pseudonym. His instincts were on the money. The movie—which never opened beyond a limited release—saw $24,487 worldwide box office receipts and was panned by critics for its crudeness and messy, unsatisfying storytelling.

Chydzik Media Group

#17. Love, Wedding, Marriage (2011)

- Director: Dermot Mulroney
- Stacker score: 33.2
- IMDb user rating: 4.8
- Metascore: 13
- Runtime: 90 minutes

When a newly married marriage counselor throws herself into saving her parents' imploding union instead of focusing on her relationship with her new husband, things go south for both couples very quickly. Mandy Moore, Kellen Lutz, James Brolin, and Jane Seymour star in the too-ridiculous-to-believe movie, which grossed just over $500,000 at the box office worldwide.

J & C Entertainment

#16. In the Mix (2005)

- Director: Ron Underwood
- Stacker score: 32.6
- IMDb user rating: 2.9
- Metascore: 31
- Runtime: 95 minutes

Usher stars in this cliché-packed movie about a man who falls in love with the mobster princess he's been employed to protect. Dubbed inconsequential and dull, the movie offers nothing to set it apart from the dozens of other "wrong side of the tracks" romances that have hit the big screen in recent years. In the end, the film lost Lionsgate an estimated $15 million.

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Fox Atomic

#15. Miss March (2009)

- Directors: Zach Cregger, Trevor Moore
- Stacker score: 31.0
- IMDb user rating: 5.0
- Metascore: 7
- Runtime: 90 minutes

A high-schooler (Zach Cregger) falls into a coma on the eve of losing his virginity to his high school sweetheart (Raquel Alessi). When he wakes up four years later, he discovers she's gone on to a glamorous life as a Playboy centerfold. The premise might have worked if there was any subtlety to the execution, but this is another movie on this list that aims for scatological humor over character-driven comedy. The obligatory Hugh Hefner cameo wasn't enough to draw in audiences, and this flop didn't even manage to clear $5 million at the box office.

MGM

#14. Material Girls (2006)

- Director: Martha Coolidge
- Stacker score: 30.4
- IMDb user rating: 3.9
- Metascore: 17
- Runtime: 98 minutes

In this loose (emphasis on the loose) retelling of Jane Austen's "Sense and Sensibility," Hilary and Haylie Duff must save their reputations and their father's business after a scandal threatens to destroy everything. Intended for teenage audiences, the movie didn't concern itself with imparting serious lessons or stressing believability, which were both strikes against it as far as critics were concerned. Tween girls disagreed, spending $11.5 million on tickets at domestic box offices and another $12 million in DVD sales.

Hi-Rez Films

#13. Whipped (2000)

- Director: Peter M. Cohen
- Stacker score: 29.9
- IMDb user rating: 4.5
- Metascore: 10
- Runtime: 82 minutes

Tiresome, vulgar, and unfunny are the words critics most commonly use to describe "Whipped." When three friends fall for the same woman (Amanda Peet) their weekly bar hang goes from swapping stories about their sexual escapades to an all-out war over her affections. Fans seemed to agree with the critics' take, and the movie only earned $1 million more than its $3 million budget upon release.

Full Sail Films

#12. Larry the Cable Guy: Health Inspector (2006)

- Director: Trent Cooper
- Stacker score: 29.9
- IMDb user rating: 3.4
- Metascore: 21
- Runtime: 89 minutes

Now working as a health inspector, Larry the Cable Guy and his new partner must solve the mystery of a food poisoning epidemic while also solving the mystery of one another's hearts. Unfortunately, the crude humor of "Larry the Cable Guy" doesn't work for everyone, and many audiences were turned off by the film's jokes despite its half-decent storyline, as evidenced by its paltry $15.7 million box office draw.

Screen Gems

#11. Swept Away (2002)

- Director: Guy Ritchie
- Stacker score: 29.3
- IMDb user rating: 3.6
- Metascore: 18
- Runtime: 89 minutes

Writer and director Guy Ritchie's biggest mistake in his 2002 "Swept Away" remake? Casting his then-wife Madonna, who had already proven herself to be a less-than-inspiring actress, as the film's protagonist. Madonna plays a bougie socialite who falls in love with a deckhand after the two find themselves stranded on a desert island after a boat crash. The film was received so poorly it is often included in worst films of all time lists and grossed just a tenth of its budget back at the box office.

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Alive Films

#10. Cool as Ice (1991)

- Director: David Kellogg
- Stacker score: 28.8
- IMDb user rating: 2.9
- Metascore: 24
- Runtime: 91 minutes

Developed specifically to be Vanilla Ice's film debut, "Cool as Ice" sees the rapper play a motorcycle-riding bad boy who falls in love with an honor student. Their romance hits a speed bump when her father, who is in a witness protection program, finds himself on the run once again. Like many other celebrity vehicles, the film earned back just a fifth of its budget at the box office with critics citing the musician's lackluster performance as its main issue.

Twentieth Century Fox

#9. Two of a Kind (1983)

- Director: John Herzfeld
- Stacker score: 28.3
- IMDb user rating: 4.7
- Metascore: 5
- Runtime: 88 minutes

Following the massive success John Travolta and Olivia Newton-John had with "Grease," it's not surprising that studios would want to reunite the pair, thinking their chemistry would guarantee another box office smash. Unfortunately, they gave them this trainwreck of a plot to work with (he plays a robber, she a bank teller, and they must work together to find common ground lest God unleashes another Noah-level flood). Try as they might to turn this garbage into gold, the pair just couldn't make it work, and the movie was a critical failure (though its soundtrack was a commercial success).

HandMade Films

#8. Shanghai Surprise (1986)

- Director: Jim Goddard
- Stacker score: 26.1
- IMDb user rating: 3.2
- Metascore: 16
- Runtime: 97 minutes

Madonna strikes out yet again with "Shanghai Surprise." The singer plays a missionary nurse on the hunt for a supply of opium to ease the pain of her patients. Her then-real-life husband, Sean Penn, plays her love interest, a glow-in-the-dark tie salesman who agrees to help her find the illegal drug. The poorly written flop was produced by former Beatle George Harrison, but even his involvement couldn't save the corny film from the Razzie awards.

Big Screen Entertainment Group

#7. Dirty Love (2005)

- Director: John Asher
- Stacker score: 23.9
- IMDb user rating: 3.5
- Metascore: 9
- Runtime: 91 minutes

Jenny McCarthy wrote and starred in this miscalculated story of a girl who tries to reenter the dating world after a messy breakup. While some critics found McCarthy's on-screen presence charming, they were less impressed with her screenwriting abilities, particularly in the comedy department. Her then-husband John Asher directed the picture, and it's perhaps no coincidence that the couple divorced the month it was released. Critically panned and a bomb at the box office, this movie failed on all counts.

Revolution Studios

#6. Gigli (2003)

- Director: Martin Brest
- Stacker score: 23.9
- IMDb user rating: 2.6
- Metascore: 18
- Runtime: 121 minutes

One of the worst commercial flops in history, "Gigli" made back $7.2 million of its $54 million budget. The story follows a romance that develops between two kidnappers, and it was derided as bizarre and poorly paced by critics. The lack of on-screen chemistry between stars Ben Affleck and Jennifer Lopez—who, during filming, were involved in the highly publicized "Bennifer" romance—made for easy fodder for late-night comedians. Ben Affleck has acknowledged the poor quality of the film in several interviews.

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New Regency Pictures

#5. Date Movie (2006)

- Directors: Aaron Seltzer, Jason Friedberg
- Stacker score: 21.2
- IMDb user rating: 2.8
- Metascore: 11
- Runtime: 83 minutes

When the best blurb you can come up with for your movie poster is "from 2 of the 6 writers of Scary Movie," you know you've got a real gem on your hands. An extremely broad comedy that fails to be funnier than the movies it parodies, "Date Movie" focuses on the build-up to a wedding between a formerly overweight bride (Alyson Hannigan) and a (supposedly) charming Englishman (Adam Campbell). The movie grossed a respectable $48.5 million in domestic sales, but its poor critical reception ended any hopes Hannigan might have had for a movie career beyond the "American Pie" franchise.

Thinkfactory Media

#4. 10 Rules for Sleeping Around (2013)

- Director: Leslie Greif
- Stacker score: 20.1
- IMDb user rating: 3.6
- Metascore: 1
- Runtime: 94 minutes

For a sex comedy, "10 Rules for Sleeping Around" has very little sex and very little comedy. It follows two couples, one more sexually open and the other fairly straightlaced, who try and impart a few of their own beliefs on the other while at a party in the Hamptons. But rather than share any of those rules with us, or tell us any jokes to distract us from the fact that they aren't sharing those rules with us, the film just rambles and gives us scene after scene of poorly acted filler.

Point Park University

#3. Not Cool (2014)

- Director: Shane Dawson
- Stacker score: 20.1
- IMDb user rating: 3.6
- Metascore: 1
- Runtime: 93 minutes

YouTuber Shane Dawson directed and produced "Not Cool" for the Starz reality competition series "The Chair." Using the same screenplay as the other films in the competition, the movie follows a group of high school friends who reunite over their various colleges' Thanksgiving break. His version of the story is replete with raunchy jokes, profanity, ethnic stereotypes, and caricatures instead of characters. Critics hated it and slammed it as a terrible and vile piece of storytelling.

19 Entertainment

#2. From Justin to Kelly (2003)

- Director: Robert Iscove
- Stacker score: 17.9
- IMDb user rating: 1.9
- Metascore: 14
- Runtime: 81 minutes

Coming off their success as the winner and runner-up of American Idol's first season, Kelly Clarkson and Justin Guarini starred in this ill-fated musical rom-com that follows a college student (Guarini) on spring break in Florida, who falls for a waitress (Clarkson). A jealous friend, a lost phone number, and far too many song-and-dance tunes ensue. The film could not even crack $5 million at the worldwide box office on a $12 million budget.

Purple Pictures

#1. The Hottie & the Nottie (2008)

- Director: Tom Putnam
- Stacker score: 14.1
- IMDb user rating: 1.9
- Metascore: 7
- Runtime: 91 minutes

This 2008 Paris Hilton vehicle was a commercial and critical misfire, grossing less than $30,000 domestically. The plot centers on Paris Hilton, the titular "hottie," sexually blackmailing a potential suitor into finding a boyfriend for her homely best friend. Critics eviscerated the film for its over-reliance on gross-out humor and shallow subject matter. In 2010, Paris' wooden performance helped her to clinch the "Worst Actress of the Decade" win at the 30th annual Razzie Awards.

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