The 50 Worst Romantic Comedies

We have neither love nor laughs for these heartbreakingly bad movies.

Dec 05, 2012
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Every man has been dragged to a romantic comedy against his will. Most of us have been lured into multiple nights of romcoms, always believing that they will increase our chances of getting into a woman’s pants, and usually being wrong. There are those lovely times, however, when the movie itself is worth it, regardless of how things play out afterwards. But, we are not here today to talk about anything so enjoyable and hilarious as Annie Hall, Love Actually, and When Harry Met Sally. In fact, we want to explore films that are just the opposite.

These are films that might actually turn off or even repulse the viewer and turn down the heat in any room. There is no chance that these films will put your lady in the mood for love. We’ve taken a bullet for you all and identified the worst chick flicks, so you don’t have to chance sitting through one on your quest to unlock your lady’s chastity belt. These are The 50 Worst Romantic Comedies.

After you read this, you’ve got nothing to complain about if you end up watching one of these on one endlessly inane night your girl, because you have been warned.

Written by Brenden Gallagher (@muddycreekU)

50. Drive Me Crazy (1999)

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Director: John Schultz
Stars: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Mark Metcalf, Ali Larter
Lame Love Song: "I Want it That Way," The Backstreet Boys
Love Conquers: Vengeance against exes

Sabrina the Teenage Witch and the always engaging Vince from Entourage as high school soul mates? How could such a film go wrong? In any number of ways, it turns out.

This romcom flips the script established by films like She's All That, as this time she is the alpha female queen bee and he is the coffee shop dwelling misunderstood weirdo who needs a makeover. That's innovation for you, folks.

The film was originally titled Next to You, but was retitled to take advantage of the synergy that could be created with the Britney Spears song of the moment, Drive Me Crazy. It's awesome when individual pieces of art can work together across forms like that. Masterful.

49. You've Got Mail (1998)

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Director: Nora Ephron
Stars: Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey, Steve Zahn, Dave Chappelle, Jean Stapleton
Lame Love Song: "Anyone at All," Carole King
Love Conquers: E-mail

You've Got Mail's status as the longest infomercial ever is enough to earn the film a spot on the list, as the title itself is an AOL trademark. Shameless shilling aside, this film does not hold up well. The Internet has come a long since the dawn of instant messaging; advances in social media make Internet anonymity much more difficult.

In recent years, the film has become further antiquated, as Tom Hanks's character works for a bookstore mega-chain trying to run poor Meg Ryan out of business. The only reason to go in a bookstore these days is because your e-reader isn't working (or because you love the smell of dead trees). As technology marches forward, this film becomes more and more stale—sort of the opposite of a fine wine.

48. Runaway Bride (1999)

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Director: Gary Marshall
Stars: Julia Roberts, Richard Gere, Joan Cusack, Christopher Meloni, Donal Logue
Lame Love Song: "I Never Saw Blue LIke That," Shawn Colvin
Love Conquers: Commitment issues

There's nothing like a local news human interest story turned into a two-hour film. Though much strains the limits of credulity in this film, the thing that gets us most is that a national newspaper sends a columnist (Gere) to investigate a woman (Roberts) who has jilted guys at the alter three times—talk about a slow news day.

USA Today isn't exactly known for its trophy shelf of Pulitzers, but wasn't there an American Idol or The Voice recap article to run on the front page instead?

47. She's All That (1999)

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Director: Robert Iscove
Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Kevin Pollak, Anna Paquin, Kieran Culkin, Usher Raymond, Lil' Kim, Gabrielle Union
Lame Love Song: "Kiss Me," Sixpence None the Richer
Love Conquers: High school social hierarchy

She's All That makes the list not only for its poor quality, but the lasting impact the film had on romcom clichés. The movie reminded us that if only a girl were to take off her glasses and let down her ponytail, she might, in fact, be totally hot. This cliché innovation launched more copycats than the Unabomber (topical, we know), and the tween romcom landscape was never the same.

While high school boys are completely dense, it is hard to believe that their vivid masturbatory imaginations can't conjure up an image of a chick without glasses and with her hair down. But, hey, at least the film provides a positive message for young women. It is OK to be a little different, to march to the beat of your own drum—as long as you have a banging body underneath those paint-speckled overalls.

46. Home Fries (1998)

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Director: Dean Parisot
Stars: Drew Barrymore, Catherine O'Hara, Luke Wilson, Juke Busey, Shelley Duvall
Lame Love Song: "Magic Moments," Perry Como
Love Conquers: Rednecks

Breaking Bad mastermind Vince Gilligan wrote this script, proving true Groucho Marx's immortal words, "They can't all be gems." Putting your leading lady in bed with multiple men from the same family is a surefire way to earn worst romcom status, no matter how tight your writing chops. Even Gilligan's brilliance couldn't save this tale of a woman (Barrymore) who falls for the stepson (Wilson) of the dead guy she used to bone.

45. Maid in Manhattan (2002)

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Director: Wayne Wang
Stars: Jennifer Lopez, Ralph Fiennes, Natasha Richardson, Stanley Tucci, Amy Sedaris
Lame Love Song: "Come Away with Me," Norah Jones
Love Conquers: Social class

There is usually nothing romantic about the circumstance in which a rich politican ends up waking up with a maid in his hotel room. Though we aren't quite as put off by this film as we are by such real-life political sex scandals, it is close.

One of the most favorable reviews of the film at the time of its release came from Time Out, which called the film "painless." Though that is a positive review for a cancer procedure, it isn't enough to sell you on another romcom featuring the dynamic screen presence of "Jenny from the Block."

44. Employee of the Month (2006)

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Director: Greg Coolidge
Stars: Dane Cook, Jessica Simpson, Dax Shepard
Lame Love Song: "Can't Fight This Feeling," REO Speedwagon
Love Conquers: Working for a warehouse club chain

What Hollywood executive found Dane Cook and his trademark "shocker" gesture so charming that they thought that he would make a great leading man in a movie about employees at a fake Costco chain competing for the affections of a lady cashier? Unfortunately for Mr. Cook, and the sorry son a bitch who made a bet on him, while you can steal jokes, you can't steal dramatic talent.

To be fair, pairing him with co-star Jessica Simpson didn't help matters, as her only previous acting experience consisted of a guest spot on the Twightlight Zone reboot, Dukes of Hazzard, and playing herself in a reality show.

43. When in Rome (2010)

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Director: Mark Stephen Johnson
Stars: Kristen Bell, Josh Duhamel, Anjelica Huston, Will Arnett, Jon Heder, Dax Shepard, Danny DeVito, Bobby Moynihan, Kristen Schaal
Lame Love Song: "Honey Let me Sing You a Song," Matt Hines
Love Conquers: A magic fountain

Two of our least favorite romcom clichés are 1) making the main character an art gallery curator, architect, or interior designer—because these jobs are, like, artsy, but not, like, too artsy—and 2) making a hot actress clumsy so we feel like she is "just like us."

When in Rome does both. While many studio romcoms go back to the well of clichés, only truly awful films can combine such trite, stale plot points with an entirely stupid premise. When in Rome achieves the perfect combination of cliché and absurdity with its story of a young career woman (Bell) who finds herself pursued by numerous suitors after she steals coins from a magical fountain.

42. Made of Honor (2008)

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Director: Paul Weiland
Stars: Patrick Dempsey, Michelle Monaghan, Whitney Cummings, Sydney Pollack, Chris Messina
Lame Love Song: "Love Song," Sara Bareilles
Love Conquers: Platonic friendship

Sometimes it seems like Hollywood filmmakers think of the pun first and then create a concept for a film that fits their clever title. Made of Honor unfolds just how you would expect: Patrick Dempsey's character is asked to be the "maid of honor" for his best friend's wedding—only to discover that *gasp* he is love with her.

We think the story would be more interesting from the fiancé's point of view, as there would be numerous compelling questions to explore. What did dude expect to happen when his fiancée's "best friend" is a muscular, five-o'clock shadowed, wealthy guy? We all remember what Chris Rock said about platonic male/female friends....

41. Valentine's Day (2010)

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Director: Garry Marshall
Stars: Jessica Alba, Kathy Bates, Jessica Biel, Bradley Cooper, Patrick Dempsey, Jamie Foxx, Jennifer Garner, Topher Grace, Anne Hathaway, Ashton Kutcher, Queen Latifah, Taylor Lautner, Taylor Swift
Lame Love Song: "Jump Then Fall," Taylor Swift
Love Conquers: Valentine's Day

Casting directors Deborah Aquila and Tricia Wood must be the only people involved in this star-stuffed Love Actually rip-off with a sense of humor. It seems they took twisted pleasure in putting together the worst possible on-screen pairs Hollywood could muster.

Ashton Kutcher and George Lopez play best friends in this film, which would make for the most annoying fishing trip known to mankind. Taylor Lautner and Taylor Swift play love interests, which likely amounts to the most boring couple ever. In defense of the film, it did win a number of awards. Unfortunately, they were Teen Choice Awards, and the prestigious MTV Movie Award for Best Kiss.

40. Just Go with It (2011)

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Director: Dennis Dugan
Stars: Adam Sandler, Jennifer Aniston, Nicole Kidman, Nick Swardson, Brooklyn Decker, Dave Matthews, Kevin Nealon
Lame Love Song: "Every Breath You Take," Sting
Love Conquers: Lying

After The Waterboy, we knew it was only a matter of time until Adam Sandler was recognized as America's answer to Hugh Grant? And what better a romantic premise than a man who fakes being married in order to get hot women into bed?

The only reason we could find to watch this film is the presence of Brooklyn Decker. If that is a draw for you, might we suggest picking up a copy of the 2010 Sports Illustrated Swim Suit issue, in which she gives a far more credible performance as a woman wearing bikinis.

39. Chances Are (1989)

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Director: Emile Ardolino
Stars: Cybill Shepard, Robert Downey Jr., Ryan O'Neal, Mary Stuart Masterson
Lame Love Song: "Forever Young," Rod Stewart
Love Conquers: Incest

Rarely does an actor get one chance to star in a romantic comedy about misplaced souls. Robert Downey Jr. got to star in two: Heart and Souls, and this gem, Chances Are (drugs are one thing, but it's really impressive that he made a comeback from this dud).

Not only is Robert Downey Jr. a reincarnated soul here, but he also comes back as a young man who falls in love with a woman who he later finds out was his daughter in his previous life. Of course, he feels attracted to the daughter's mother, who was his wife back in the day.

Man, in Ancient Greece, you got your eyes poked out for this sort of thing. There's the decline of Western Civilization for you.

38. Fever Pitch (2005)

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Director: The Farrelly Brothers
Stars: Drew Barrymore, Jimmy Fallon, Jason Spevack, Jack Kehler
Lame Love Song: "Northern Sky," Nick Drake
Love Conquers: Baseball fanaticism

We'll never know what it was about Jimmy Fallon's constantly cracking-up sketch-ruining performances on SNL that made someone think he was leading man material. We have much love for his talk show, but wow, what a long, tortured road it was to get there.

Luckily, Fever Pitch (inspired by Nick Hornby's excellent book about being a lifelong Arsenal fan) and Taxi were enough to convince America that Fallon was not built to star on the silver screen. It surpassed no one that Fever Pitch, the story of a man who believes that the Boston Red Sox are more important than the woman he loves, but learns that they are of relatively equal importance, didn't turn Fallon into a latter-day Cary Grant.

37. Summer Catch (2001)

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Director: Michael Tollin
Stars: Freddie Prinze Jr., Jessica Biel, Matthew Lillard
Lame Love Song: "Over my Head," Semisonic
Love Conquers: Baseball

For five years or so, Freddie Prinze Jr. was a god. It is so easy to laugh, looking back on the films he made, but the man was a presence in the hearts and on the bedroom posters of pretty much every tween in the late '90s.

The problem, of course, was that his movies sucked, and when your movies suck you can go from box office glory to the George Lopez Show in no time. Though he's only be a hero to us writers of bad movie lists these days, the man was a king, even if for a brief, spiky-haired, cargo pant wearing, wallet-chain having moment.

36. Over Her Dead Body (2008)

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Director: Jeff Lowell
Stars: Eva Longoria, Paul Rudd, Lake Bell, Jason Biggs
Lame Love Song: "Love," Matt White
Love Conquers: The ghost of a jealous ex-girlfriend

This film does a service to humanity by bringing to light an issue that has been plaguing society: the dangers of ice sculpting while drunk.

Kate (Longoria) dies on what would have been her wedding night due to the actions of a negligent ice sculptor. Kate is not happy with her untimely demise, as anyone who suffers death by ice sculpture would rightly be, and does what any unhappy dead person does: haunts her fiancé, preventing him from dating other women.

We would have had an easier time with the film if the studio had kept the original title, which was (we swear) Ghost Bitch.

35. Monster-in-Law (2005)

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Director: Robert Luketic
Stars: Jennifer Lopez, Jane Fonda, Wanda Sykes, Adam Scott, Will Arnett, Elaine Stritch
Lame Love Song: "Everyday is a Holiday (with You)," Esthero
Love Conquers: The Mother-in-Law

"Bitchy Mother-in-Law" is probably one of our least favorite cinematic stereotypes. Not only does it invite performances as flat and predictable as the "manic pixie dream girl" or the "hooker with a heart of gold," but you can't help but feel bad for the actress playing the role.

Like Jane Fonda, the actress is usually an ex-bombshell who stopped working for a decade, and her only way back to Hollywood is to play a petulant battle-ax. Damn it, the woman won the Oscar for Best Actress—twice! She deserves better.

34. I Now Pronounce You Chuck and Larry (2007)

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Director: Dennis Dugan
Stars: Adam Sandler, Kevin James, Jessica Biel, Dan Aykroyd, Ving Rhames, Steve Buscemi, Rob Schneider, Rachel Dratch, Nick Swardson
Lame Love Song: "You're Beautiful," James Blunt
Love Conquers: Insurance fraud

I Now Pronounce You Chuck and Larry is impressive in just how far the film goes out of its way to be offensive. Granted, the premise is likely to offend the LGBT community no matter how you slice it. But, with flourishes like casting Rob Schneider as a character in yellow face, the film goes above and beyond to alienate any potential audience.

Original screenwriter Alexander Payne had his name removed from the script after he claimed Happy Madison "Sandlerized" it. It's been a long time since the one-two punch of Billy Madison and Happy Gilmore, Mr. Sandler. We're not sure if "Sandlerizing" even humors pre-pubescent boys anymore.

33. New Year's Eve (2011)

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Director: Garry Marshall
Stars: Michelle Pfeiffer, Zac Efron, Robert De Niro, Halle Berry, Cary Elwes, Alyssa Milano, Common, Jessica Biel, Seth Meyers
Lame Love Song: "Better Days," Goo Goo Dolls
Love Conquers: New Year's Eve

This is another one of those movies with 15 different romantic subplots and every available celebrity crammed into it. We can excuse a film built around an ensemble cast regarding Christmas or the aftermath of a war, there just aren't as many possible New Year's Eve romantic entanglements as this movie presents.

In our experience, either you get really drunk and hook up or you get really drunk and puke all over yourself after failing to hook up. Of course, a film about these two scenarios would likely be very short, which would have been a merciful relief for New Year's Eve's audiences.

On a sidenote, Robert De Niro's nurses in this film are Halle Berry and Alyssa Milano. We suspect writer Katherine Fugate raided our middle-school masturbation journal before writing this one.

32. Killers (2010)

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Director: Robert Luketic
Stars: Ashton Kutcher, Katherine Heigl, Tom Selleck, Catherine O'Hara, Rob Riggle
Lame Love Song: "Beauty in the World," Macy Gray
Love Conquers: Assassination attempts

There are few roles that Ashton Kutcher could be tapped for that are less believable than that of international assassin. Luckily, Kutcher will likely never be offered roles in any film adaptations of Shakespeare and Daniel Day-Lewis beat him out for the lead in Lincoln, so, hopefully, this is as ridiculous as it gets.

Our favorite performance of Kutcher's since That '70s Show is probably the camera commercials where he flirts with the hot chicks at the swanky party. It is no coincidence that these performances are also among his most brief.

31. Failure to Launch (2006)

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Director: Tom Dey
Stars: Matthew McConaughey, Sarah Jessica Parker, Zooey Deschanel, Justin Bartha, Bradley Cooper, Terry Bradshaw, Kathy Bates, Rob Corddry, Patton Oswalt
Lame Love Song: "Forget My Heart," Simon Steadman
Love Conquers: Living in your parents' basement


The thing we love about Matthew McConaughey (besides his stable of fine lady conquests) is that we keep getting older...and Hollywood continues to try to sell him to us as a romcom leading man.


The film is awful, but it does give us hope for all of the dudes we grew up with who are still living in their parents' basement. All they need is for their folks to hire an extremely attractive psychologist (Sarah Jessica Parker) to fake a relationship with them, manufacture a traumatic event in her life that they help her overcome, and transfer their dependence on their parents to her to really motivate them to get their own place.


We would try hiding their bong and blocking YouPorn on their browser first.


30. Return to Me (2000)

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Director: Bonnie Hunt
Stars: David Duchovny, Minnie Driver, Carrol O'Connor, Bonnie Hunt, David Alan Grier, James Belushi
Lame Love Song: "Angel Standing By," Jewel
Love Conquers: A heart transplant

You can learn so much about science simply by going to the movies. For example, did you know that if the woman you love dies, and happens to be an organ donor, you will fall in love with any woman who receives a heart transplant courtesy of your dead lover? It shocked us that sex addict David Duchovny taught us this and not our high school biology teacher.

We have since called the DOT and demanded that the "organ donor" designation be removed from our driver's licenses, because damn it, we aren't going to lose at the game of love twice. And what if your second lover dies and they give their heart to a new woman? You could be locked in an infinite loop of dying, heart transplanting girlfriends. As science marches forward, we sometimes have to ask ourselves, "At what cost?"

29. What Happens in Vegas (2008)

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Director: Tom Vaughan
Stars: Cameron Diaz, Ashton Kutcher, Rob Corddry, Jason Sudeikis, Treat Williams, Zach Galifianiakis, Qeen Latifah, Krysten Ritter
Lame Love Song: "Love," Matt White
Love Conquers: Greed

Judges have way too much power in movies. After accidental newlyweds (Ashton Kutcher!!! and Cameron Diaz) win big at a Vegas casino, a judge, played by Dennis Miller, rules they have to try to make their marriage work for six months, and if they don't, the money will be tied up in litigation.

Besides the dubious nature of tying someone's casino winnings up in litigation, the next question here is, why? While Dennis Miller is the most annoying conservative on Twitter, can't he justify his romanticized view on the sanctity of marriage some other way?

28. All About Steve (2009)

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Director: Phil Traill
Stars: Sandra Bullock, Thomas Haden Church, Bradley Cooper, Ken Jeong, DJ Qualls
Lame Love Song: "Drops of Jupiter," Train
Love Conquers: Stalking

Sandra Bullock certainly gave an awful performance in the film, but much love to Ms. Bullock for her performance following the release. Bullock attended the Razzies, accepted her "Worst Actress" award in person, gave a copy of the film to every audience member, and then went on to win the Best Actress Oscar for her lame white savior movie, The Blind Side, the next day.

An excerpt from Bullock's acceptance speech, "I'm willing to go through [the script] page by page, read the line the way I did it in the film, and if anyone wants to give me a line read of how I could've done it better.... We can do this till about 4 o'clock in the morning. Or you guys can just watch the movie and rethink your decision, and I'll show up next year and we can go out for a drink afterward." Bawse.

27. Beauty and the Briefcase (2010)

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Director: Gil Junger
Stars: Hillary Duff, Jaime Pressly, Jennifer Coolidge, Matt Dallas
Lame Love Song: "Prism of Love," Sly Silver & Sir Realist
Love Conquers: Corporate America

In Beauty and the Briefcase, Hillary Duff goes deep undercover for Cosmo to see what it's like to date a businessman. Now, remember, this was before Mad Men, so you couldn't just turn on the TV and see how wonderful a relationship with a corporate titan could be for a hot woman.

Duff's character's assignment is to "seek out a corporate job, and commence dating as many of her co-workers as possible"—because, you know, that's what a woman should use a corporate job opportunity to do. The similarities to Mad Men end there, unfortunately, as HIllary Duff fails to get into any drunken fist fights. It's too bad, because we would be all about that film, though we suspect such a film wouldn't be deemed "on-brand" for ABC Family.

26. Who's That Girl (1987)

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Director: James Foley
Stars: Madonna, Griffin Dunne, Haviland Morris, John McMartin
Lame Love Song: "What the World Needs Now is Love," Burt Bacharach
Love Conquers: Parole

Who's That Girl seemed destined to fail from the beginning. After the abysmal Shanghai Surprise, Warner Bros. wanted assurances that Madonna was "ready" to be a leading lady. Turns out she wasn't. (Nor has she ever cracked actor-musician double threat status.)

Granted, she wasn't helped by the plot, which featured a parolee falling in love with her tax attorney and scenes with a live cougar. But Madonna's indulgence in the worst of vanity vehicle clichés, like refusing to do more than one take, certainly couldn't have helped.

25. Kissin' Cousins (1964)

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Director: Gene Nelson
Stars: Elvis Presley, Arthur O'Connell, Glenda Farrell, Pamela Austin
Lame Love Song: "Tender Feeling," Elvis Presley
Love Conquers: Mistaken identity

Critics have given endless credit to Peter Sellers for playing multiple roles in Dr. Stangelove. What history easily forgets, however, is that Elvis Presley did it the same year. In Kissin' Cousins, Presley plays both an Air Force officer and his identical hillbilly cousin.

The title is slightly misleading, as the cousins do not kiss each other in a proto-Brokeback Mountain gay, incestual encounter, but rather, they kiss other women. And get this, the Air Force officer falls for a hillbilly woman, and the hillbilly cousin falls for a fiery service woman. If you like Presley here, you'll love him in his numerous other masterful cinematic performances including Clambake, Tickle Me, and Charro!

24. Simply Irresistible (1999)

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Director: Mark Tarlov
Stars: Sarah Michelle Gellar, Sean Patrick Flanery, Patricia Clarkson, Amanda Peet
Lame Love Song: "Every Little Thing (He) Does is Magic," Shawn Colvin
Love Conquers: A magic crab

A man sells Amanda (Sarah Michelle Gellar) a magical crab that can cast spells by waving its claw. At the same market where she purchases the crab, Amanda also meets the love of her life (Sean Patrick Flanery). For some reason, Gellar is endowed with magical culinary powers; for example, when she cries into food she is preparing...the person who eats it cries also! This is great, except that the man she loves thinks she might be a witch.

Unless you and the lady's date plans involve the smoking of some dank nuggs, we are going to recommend you pass on this one. So did Gene Siskel, who gave this film, the last he ever reviewed, a thumbs down.

23. Shanghai Surprise (1986)

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Director: Jim Goddard
Stars: Sean Penn, Madonna, Paul Freeman, Richard Griffiths
Lame Love Song: "Breath Away From Heaven," George Harrison
Love Conquers: Chinese Organized Crime

You are probably shocked to hear that Sean Penn and Madonna didn't exactly light up the screen together, even though they were newlyweds at the time. Things were far more exciting off-screen, as Penn landed in jail the year of film's release for assaulting a friend of Madonna's and attacking an extra on the set of At Close Range.

Though Sean Penn and Madonna didn't make it in the end, they were lucky enough to go on to have a number of destructive Hollywood relationships damaging the personal and professional lives of those involved.

22. Swept Away (2002)

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Director: Guy Ritchie
Stars: Bruce Greenwood, Madonna, Elizabeth Banks, Jeanne Tripplehorn, Adriano Giannini
Lame Love Song: "Fade into You," Mazzy Star
Love Conquers: A shipwreck


Madonna is the iron woman of awful romantic comedies. Her relationship with Sean Penn precipitated the terrible Shanghai Surprise, but the equally atrocious Swept Away was a creative collaboration between herself and husband Guy Ritchie a decade and a half later.


You have to give the Material Girl credit for persistence. No matter how often the world tells her that she is never going to be a leading lady, she turns around and manipulates a beau into a career-damaging cinematic endeavor. All of this while employing a sterilization team to protect her DNA, practicing Kaballah, and sometimes singing! Quite, umm, impressive?!


21. Grease 2 (1982)

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Director: Patricia Birch
Stars: Maxwell Caulfield, Michelle Pfeiffer, Lorna Luft, Maureen Teefy
Lame Love Song: "Girl for All Seasons," Dominic Bugatti & Frank Muskar
Love Conquers: High school social hierarchy


Though an informal poll of tween slumber parties agreed that Grease needed a sequel, we are pretty sure they would have tapped into their collective Ouiji boards to stop this film from seeing the light of day if they knew what would result.


Since almost no members of the original cast signed on, Grease 2 opted to tell the story of Sandy's English cousin (Caulfield), who was not even mentioned in the original. With songs like "Cool Rider" (which teaches him that he must become a cool biker to get the girl) and the biology-themed "Reproduction," it is a wonder that this musical didn't endure on high school and community theatre stages in the same way as the original.


20. Chasing Liberty (2004)

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Director: Andy Cadiff
Stars: Mandy Moore, Jeremy Piven, Stark Sands
Lame Love Song: "Who Needs Shelter," Jason Mraz
Love Conquers: The Secret Service

Some of you will remember 2004 as the year of Facebook's launch or the Athens Olympics. At Complex, we will remember 2004 as the year that gave us TWO films chronicling the love life of fictional first daughters.

We gave Chasing Liberty the edge over First Daughter because they went to the trouble to think of a pun for the title...and because Mandy Moore's performance in A Walk to Remember made us cry. [Ed. Note: The point of view expressed here does not represent that of anyone else on the Complex Pop Culture staff besides that of the author.]

19. First Daughter (2004)

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Director: Forest Whitaker
Stars: Katie Holmes, Michael Keaton, Lela Rochon, Marc Blucas
Lame Love Song: "The Way You Look Tonight," Matt Dusk
Love Conquers: The Secret Service

That's right, the other film about the "first daughter" falling in love is called First Daughter. This should tell you all you need to know about the originality of the film's storytelling. Things really went downhill for Katie Holmes after Dawson's Creek and flashing her breasts in The Gift, huh? It's a good thing that this film was the worst of it.... Too soon?

18. Dr. T and the Women (2000)

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Director: Robert Altman
Stars: Richard Gere, Helen Hunt, Farrah Fawcett, Laura Dern, Shelly Long, Tara Reid, Kate Hudson, Liv Tyler, Andy Richter
Lame Love Song: "She's Already Made Up Her Mind," Lyle Lovett
Love Conquers: Gynecology

With all the millions that Hollywood has to throw at projects, you'd think they could afford a guy to tell them that a romcom about a male gynecologist is an awful idea. If you don't have confidence in Richard Gere's abilities to pull off his role as an emo OB/GYN, reports that he "didn't understand the ending...until someone explained it to him" should set you at ease and rocket this bad boy right up your Netflix queue.

17. Boy, Did I Get a Wrong Number (1966)

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Director: George Marshall
Stars: Bob Hope, Elke Sommer, Phyllis Diller, Cesare Danova
Lame Love Song: n/a
Love Conquers: Adultery

A film about a man (Hope) who coaxes an actress-on-the-run (Sommer) to stay at his cabin to "protect her" and hide her from the rest of the world—if this film happens today, it is made for TV and premieres on Lifetime. Next time your grandfather crankily tries to tell you "they don't make movies like they used to," you can tell him you're OK with that.

16. Two of a Kind (1983)

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Director: John Herzfeld
Stars: John Travolta, Olivia Newton-John, Charles Durning, Oliver Reed, Scatman Crothers
Lame Love Song: "Ask the Lonely," Journey
Love Conquers: God's wrath


Five years after the release of Grease, someone decided that what Hollywood needed was another film starring John Travolta and Olivia Newton-John. With Newton-John fresh off "Let's Get Physical" and Travolta having just released Staying Alive, the shitty sequel to Saturday Night Fever, it was time to strike while the iron was luke-warm.


The film is about angels trying to get two humans to fall in love so that a vengeful God will spare a fallen world from a second flood. If there is a God, and he is on the edge in terms of his faith in the human race, we'd better hope he never sees this film.


15. Swing Your Lady (1938)

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Director: Ray Enright
Stars: Humphrey Bogart, Frank McHugh, Louise Fazenda, Mat Pendleton
Lame Love Song: "Yoo-Hoo," Al Jolson
Love Conquers: Professional wrestling

All you struggling actors out there, take note. Everybody starts somewhere. In 1938, less than five years before Bogart would star in the most romantic film of all time, he played a wrestling promoter in the Ozarks in this travesty.

You see, two professional wrestlers fall in love and won't fight. But, when the lady wrestler and female blacksmith's boyfriend shows up, things get really heated. Who better than Bogey to sort out this zany situation?

We are usually against remaking classic films, but if you could get Ashton Kutcher, the Rock, and Lucy Lawless for the remake, it might just sweep the Oscars.

14. The Beautician and the Beast (1997)

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Director: Ken Kwapis
Stars: Fran Drescher, Timothy Dalton, Ian McNeice
Lame Love Song: "Isn't it Romantic," Richard Rogers and Lorenz Hart
Love Conquers: The hardened heart of an Eastern European dictator

This film is often described as The King and I meets The Nanny, which is probably enough to get you bolting for the door. But, if you are a sucker for the age old "Eastern European dictator meets Long Island beautician" love story, this film just might be for you. 

The film is universally reviled, but director Ken Kwapis seems to actually have given a shit. He partnered with a dialect coach to create "Slovetzian," the official language of the film's fictional country, Slovetzia. One could argue that perhaps Mr. Kwapis would have done well to focus less on making up a language and more on filmmaking, but in this instance we'll opt to hate on the game and not the player.

13. The Bachelor (1999)

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Director: Gary Sinyor
Stars: Chris O'Donnell, Renee Zellweger, Artie Lange, Ed Asner, Hal Holbrook, James Cromwell, Mariah Carey, Sarah Silverman, Brooke Shields
Lame Love Song: "Your Love Keeps Lifting Me (Higher and Higher)," Jackie Wilson
Love Conquers: Money-grubbing scheming

There have been many awful romcoms through the ages, but, every so often, a love story emerges that is so distasteful all traces of love are absent. How do you do that?

Well, one way is to tell the story of an avowed bachelor and selfish prick (O'Donnell) who needs to find a bride in one day or lose his massive inheritance. Then, in a true stroke of mastery, have the climax involve dozens of money-grubbing would-be brides clawing over each other to marry said douche bag and then attempt to tear him limb from limb after being scorned.

But, at the end of the day The Bachelor was only one small step in the history of awful romcoms, and was truly a giant defeat for feminism.

12. Mannequin: On the Move (1991)

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Director: Stewart Raffill
Stars: Kristy Swanson, William Ragsdale, Meshach Taylor
Lame Love Song: "Nothing's Gonna Stop Us Now," Starship
Love Conquers: A ridiculous curse

You would think that a movie in which the leading lady is a mannequin (Swanson) would be awful. Not so fast. You see, she is the subject of a curse, and he is a reincarnated prince (Ragsdale) who has the power to lift the curse. And they have to contend with (we shit you not) an evil sorcerer by the name of Count Gunther Spretzle. Yeah, we would have preferred if it was just 120 minutes of mannequin as well.

11. My Boss's Daughter (2003)

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Director: David Zucker
Stars: Ashton Kutcher, Tara Reid, Molly Shannon, Terence Stamp, Andy Richter, Michael Madsen
Lame Love Song: "If I Had A Million Dollars," Barenaked Ladies
Love Conquers: His boss

You'll never guess what this one's about! And, would you believe it, the guy's boss (Stamp) is a total jerk! And the boss's daughter (Reid) has no idea that the employee (Kutcher at his worst/finest) has feelings for her!

There is something special about a film that offers nothing but hackneyed clichés, a film in which you can predict every turn of the plot, even down to the smallest moments. As you watch Kutcher's character deliver an impromptu mammogram to a stranger, you instinctively know that the boss's daughter will walk in mid-feel, suspecting the worst. The only thing you don't know before it happens is when you will simply give up and start begging for death's icy hand to put an end to your suffering.

10. Good Luck Chuck (2007)

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Director: Mark Helfrich
Stars: Dane Cook, Jessica Alba, Mackenzie Mowat, Dan Fogler
Lame Love Song: "I Want to Know What Love Is," Foreigner
Love Conquers: A "sexual good luck charm" jinx

Richard Roeper said this of Good Luck Chuck, the Dane Cook vehicle in which he plays a man who is saddled with a curse that every woman he has sex with will marry the next guy they date: "There is a scene in this movie where a penguin bites Dane Cook in the crotch. I'd like to find that penguin and buy it a drink." We think that about sums it up.

9. Mr. Wrong (1996)

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Director: Nick Castle
Stars: Ellen DeGeneres, Bill Pullman, Joan Cusack, Dean Stockwell, John Livingston, Robert Goulet
Lame Love Song: "I Want to Know What Love Is," Mick Jones
Love Conquers: A psychopath

Not even a film starring Dane Cook and Ashton Kutcher as brothers who both work as architects and are both in love with Katherine Heigl could kill a romcom as fast as Bill Pullman's turn as a stalking, kidnapping, jilted lover does here. Even the man who delivered the immortal presidential speech in Independence Day and the dancing talk show host herself couldn't save this awful film.

8. Dirty Love (2005)

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Director: John Mallory Asher
Stars: Jenny McCarthy, Eddie Kay Thomas, Carmen Electra, Guillermo Diaz
Lame Love Song: "Think of Me From Away While I'm in New York," The Rumor Mill
Love Conquers: Being hung up on an ex-boyfriend

There are many bad romantic comedies out there, but are there many films that are so bad that they end marriages? That's what happened with Dirty Love. Legitimately funny and hot lead actress Jenny McCarthy was married to director John Asher, and they split one month after the film's release.

In the film, McCarthy's best friend, played by Carmen Electra, tries to set her up on dates, and we can't help but feel the film would have outperformed its $35,000 box office if she had offered Jenny a different, more erotic, kind of comfort. Likely, if the film had taken such a turn, the motivations of the characters would have been clearer and the final product would have been less offensive.

7. Say It Isn't So (2001)

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Director: J.B. Rogers
Stars: Heather Graham, Chris Klein, Sally Field
Lame Love Song: "Everyone Can Fly," Gigolo Aunts
Love Conquers: Incest

Nothing says romance like incest—at least that is what this "comedy" would have you believe. For those not sufficiently put-off by the incest plot, there is plenty of masturbation, sexual predator, and necrophilia humor to shake your faith in humanity. The crowning achievement of the film is probably when the protagonist finds himself with his hand in a cow's rectum. Ahh, romance.

6. Blame It on Rio! (1984)

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Director: Stanley Donan
Stars: Michael Caine, Joseph Bologna, Valerie Harper, Michelle Johnson, Demi Moore
Lame Love Song: "Alone with Me," Lisa Roberts
Love Conquers: Pedophilia


For his last film, Singin' in the Rain director Stanley Donen opted to take on the light-hearted issue of pedophilia. The pedophilia is justified though, because, dude, Michelle Johnson's character really wants it from Michael Caine's character, Matthew Hollis.


But, wait, she is the teenage daughter of his best friend. Don't worry though, 'cause the friend has been banging Matthew's wife, so it's cool. But, then Caine's daughter tries to commit suicide by ODing on birth control pills... Yeah, kind of hard to explain that one away.


We should have known how this one was going to go, you see we didn't tell you who plays Caine's daughter—none other than Demi Moore, who used to be married to...Ashton Kutcher!


*In Capt. Kirk voice* Asssssshhhhhttoooonnnnnn! His spectre even looms over awful romcoms of the past.


5. In the Mix (2005)

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Director: Ron Underwood
Stars: Usher Raymond, Chazz Palminteri, Emmanuelle Chriqui
Lame Love Song: "Could This Be Love," One Chance
Love Conquers: Organized Crime

And here we always thought "Last Night a DJ Saved My Life" was a figure of speech, but when Usher's DJ character saves the life of a mafia don in In the Mix, a metaphor becomes reality.

The mix master is rewarded with a job protecting the Don's daughter (Chriqui) who is, you guessed it, quite attractive. Standing in their way is a douchey fiancé named Chad, because, apparently, every douchey fiancé in any movie ever has to be named Chad.

We'll stop there, because we don't want to spoil the film for you if you are naive enough to think that Usher could lose a woman's heart to a guy named Chad.

4. Gigli (2003)

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Director: Martin Brest
Stars: Ben Affleck, Jennifer Lopez, Justin Bartha, Lainie Kazan, Christopher Walken, Lenny Venito, Missy Crider, Al Pacino
Lame Love Song: "Love the One Your With," Stephen Stills
Love Conquers: Organized crime

You already know the story of Gigli. It was dropped from the majority of theaters after one week. The film won every major Razzie Award. It killed Ben Affleck's career as a leading man (until he made his glorious comeback as an auteur). The film was even recognized by the Global Language Monitor as having a tangible impact on the English language, as Gigli was 2003's synonym du jour for "terrible."

There is one silver lining though; the word "fuck" was used 124 times in the film, which would have made 14-year-old you giggle if your older brother was masochistic enough to take you to see this story of a mobster (Affleck) falling for a lesbian (Jennifer Lopez).

3. From Justin to Kelly (2003)

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Director: Robert Iscove
Stars: Kelly Clarkson, Justin Guarini
Lame Love Song: "Timeless," Kelly Clarkson and Justin Guarini
Love Conquers: Losing his phone number

Who would have thought that American Idol wouldn't end up a Hollywood star-making vehicle? The problem with awful ideas is that sometimes people think they can make money on them. Justin Guarini's career is just one of many that have been snuffed out this way.

Just how bad is From Justin to Kelly, a film who's major plot point is that one character loses another's phone number? The production company wouldn't even allow screenings for critics. Woof.

2. Phat Girlz (2006)

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Director: Nnegest Likké
Stars: Mo'Nique, Jimmy Jean-Louis, Godfrey, Kendra C. Johnson
Lame Love Song: "(You Make Me Feel Like) A Natural Woman," Aretha Franklin
Love Conquers: Weight issues

The plot of this film is based on the idea that Nigerian dudes like fat chicks, and while we can't confirm or deny that, we don't think this is the ideal premise for a romantic comedy. The film's turning point involves Mo'Nique temporarily ceasing her diet and cleaning her room, which we don't think is the ideal turning point for a romantic comedy. The climax of the film involves the Nigerian guy clearing up a relatively minor misunderstanding between him and Mo'Nique, which we don't think is an ideal ending for a romantic comedy.

This feather-light plot doesn't sound as much like a movie as it does a 90-minute  Lane Bryant commercial.

1. The Hottie and the Nottie (2008)

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Director: Tom Putnam
Stars: Paris Hilton, Joel David Moore, Christine Lakin, Johann Urb
Lame Love Song: "Meet Me in the Morning," David Hopkins
Love Conquers: An ugly best friend

The players in American pop culture should band together and resolve that they will no longer produce vanity projects for rich women famous for making sex tapes. That would, of course, only happen if we as a culture lost interest in celebrity sex tapes, which we never will. It looks like, then, we will continue to get exactly what we deserve: films like The Hottie and the Nottie.

It is hard to disparage The Hottie and the Nottie, but only because most possible negative things have already been written about it. Or perhaps more accurately, as IGN noted in its review, "there are no words to adequately express how clumsy, trite, and deeply offensive it is from start to finish."

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