Ranked: 20 Worst Chick Flicks of the Past 20 Years

Someday your Prinze will come

While there may not be a foolproof definition of the unfortunate yet helpful genre label "chick flick," there are certain indicators that most people can agree on. For example, most if not all films that fall in the romance or romantic comedy genres are typically also considered to be chick flicks. Likewise, if a film -- like this week's Julia Roberts vehicle Eat, Pray, Love -- is based on a "chick lit" book, it automatically qualifies as a chick flick. In fact, any film that uses the word "love" in the title -- or, even better, "bride" or "wedding" -- is almost certain to be a chick flick. The same goes for any film marketed with a poster that uses plenty of pinks or purples, an especially cheerful (and possibly lowercase) font, and a large, smiling photograph of an attractive woman and/or Matthew McConaughey.

So you may not be able to say precisely what a chick flick is -- other than that it is supposed to appeal to women in some way while simultaneously repelling male moviegoers -- but you know one when you see one. And we know bad movies when we see them ... like the 20 films listed below, which represent some of the worst examples that the genre has produced over the last two decades. We are not dismissing the genre as a whole; there certainly are quality films in the chick flick category, and we'll get to those later this week in a separate article. First, however, let's look at just how bad these movies can get.

Note that although we have slotted in a few older movies that aren't in our database (and thus don't have Metascores) according to a quick sampling of their reviews, we are ranking the films in score order here -- which means that however much we'd like to put titles like Ghost 51 or Maid in Manhattan 45 on this list, we cannot.

The 20 Worst Chick Flicks Since 1990

1. Down to You (2000) Add to Netflix Queue

"No one expects a light teen romance to be 'Madame Bovary,' but this is Colorforms filmmaking."

--Maitland McDonagh, TV Guide

Part chick flick, part teen comedy, the widely panned film chronicles the budding romance between college students played by Julia Stiles and Freddie Prinze Jr. Down to You tries a bit too hard to be unconventional -- the characters repeatedly talk to the camera, Selma Blair plays a porn star, and Ashton Kutcher plays a Jim Morrison wannabe named Jim Morrison -- but the result is still a formulaic bore.

2. I Hate Valentine's Day (2009) Add to Netflix Queue

"This is probably the year's worst romantic comedy -- and that's saying something in a year that includes 'Ghosts of Girlfriends Past' and 'Whatever Works.'"

--Claudia Puig, USA Today

If you blinked, you missed last year's directorial debut for screenwriter and actress Nia Vardalos, who previously penned the much more successful My Big Fat Greek Wedding 62. Consider yourself lucky: the central gimmick of a woman (Vardalos herself) who insists on going on just five dates with each prospective suitor -- no matter how well things are going -- is about as contrived as they come, and the audience can't help but be annoyed by the ensuing romantic problems that are her own, wholly unnecessary creation.

3. All About Steve (2009) Add to Netflix Queue

"Just when you think your jaw can't drop any lower in appalled amazement, comes a romantic comedy so lunkheaded and ill-conceived that it makes your average, idiotic Kate Hudson-Matthew McConaughey outing look like the reincarnation of Hepburn and Grant."

--Stephanie Zacharek, Salon.com

Sandra Bullock pulled off perhaps the rarest achievement in acting history in 2009: winning both an Oscar and a Razzie in the same year. Here, in her Razzie-winning performance, she plays one of the least likable protagonists of any film in recent memory: a crossword-puzzle designer who obsessively stalks a cameraman (Bradley Cooper) after going on one blind date with him. What in theory could have been a terrifying portrait of one woman's descent into insanity is instead played as a wacky romantic comedy ... except that few moviegoers actually found it funny.

4. Swept Away (2002) Add to Netflix Queue

"A shrill, amateurish two-character play that demeans women and leaves men with the quaint notion that the best way to a woman's heart is through enslavement."

--Jack Mathews, New York Daily News

While most of director Guy Ritchie's stylishly violent films are heavily geared toward male moviegoers, he took a detour in 2002 to direct his then-wife Madonna in this romantic comedy remake of Lina Wertmuller's 1974 classic of the same name. Big mistake. Madonna's performance may have been terrible, but critics found the film's drama laughable and its attempt at comedy tragic, and audiences wisely stayed away.

5. Bride Wars (2009) Add to Netflix Queue

"An insipid comedy in which the women are shallow, acquisitive, backstabbing, selfish harridans."

--Connie Ogle, Miami Herald

Apparently, 2009 was not a banner year for the chick flick genre, though Bride Wars was at least a commercial if not critical success. Gary Winick's rom-com wastes the inherent likability of its leads (Anne Hathaway and Kate Hudson) by making the entire film into one long, drawn-out and increasingly nasty fight between their characters, two one-time friends who want to hold their weddings in the same place on the same day.

6. Mr. Wrong (1996) Add to Netflix Queue

"On screen every one is running around as though it were a comedy. But in the theater, no one is laughing."

--Mick LaSalle, San Francisco Chronicle

Another movie that mistakenly believes that crazed stalkers make for hilarious romantic comedy, Mr. Wrong almost single-handedly ended the film career of comedian Ellen DeGeneres just as it was starting. In her first leading big-screen role (as the woman being stalked by a strangely-used Bill Pullman), DeGeneres is actually one of the film's few high points; critics felt that the real Mr. Wrong was director Nick Castle, though he wasn't responsible for the awful script.

7. Autumn in New York (2000) Add to Netflix Queue

"To say that it's dull barely scratches the surface."

--Michael Atkinson, Mr. Showbiz

Actress-turned-director Joan Chen helmed this sappy May-September romance starring Winona Ryder and Richard Gere who -- surprise, surprise -- have zero chemistry together on screen. Ryder's character spends most of the movie dying from a major illness; if you watch, you'll spend much of the running time dying from boredom (unless you find the sight of Gere making out with Ryder enjoyably wrong). Only a decent foreign take allowed the film to recoup its unusually large $65 million budget.

8. When in Rome (2010) Add to Netflix Queue

"Even the most ardently romantic suspender of disbelief is going to have a hard time successfully escaping into the preposterously awful world of When In Rome. It’s a place where all the situations, characters, and dialogue are drawn so broadly, the script must have been written with a paint roller."

--Tasha Robinson, A.V. Club

Thanks to the goodwill generated by Veronica Mars, we're willing to forgive Kristen Bell a few misfires here and there. But if she chooses any more projects as inept as When in Rome, the actress might find herself losing fans quickly. This absolutely generic romantic fantasy finds Bell playing a New Yorker who attempts to find love through the aid of magic coins plucked from a Roman fountain, which could have been mildly diverting if borderline-incompetent director Mark Steven Johnson (Ghost Rider 35, Simon Birch 39) bothered to take advantage of the Italian setting, or if the script's attempts at humor were even remotely funny.

9. Georgia Rule (2007) Add to Netflix Queue

"There's something unsavory about the way it uses a character's emotional and psychological scars as a gimmick, a way for us both to enjoy the vision of Lohan in a series of skimpy baby-doll mini-dresses even as we're ultimately supposed to murmur, 'Poor little thing, no wonder she's so sexually precocious!'"

--Stephanie Zacharek, Salon.com

If Lindsay Lohan isn't the worst thing about your movie, you know you have problems. Lohan, basically playing a version of herself, earned notoriety for her behavior on the set, but her on-screen performance -- as the youngest third of a multi-generational trio of women that also includes Jane Fonda and Felicity Huffman -- is surprisingly decent. Still, the script from Ya-Ya Sisterhood scribe Mark Andrus can't decide if it's a melodrama or a light comedy, and Georgia Rule ultimately succeeds at neither.

10. A Cinderella Story (2004) Add to Netflix Queue

"They took the most famous tale in the world and broke it."

--Stephen Hunter, Washington Post

A modern-day teen remake of Cinderella starring Hilary Duff? How could that possibly go wrong? (Perhaps the part about it being "a modern-day teen remake of Cinderella starring Hilary Duff.") About as unmagical and charmless as a fairy tale can get, and severely dumbed-down from a story that wasn't exactly Gravity's Rainbow to begin with, the high school-set Cinderella Story does provide a fine showcase for a terrible performance by Duff -- not that the rest of the cast is much better.

11. License to Wed (2007) Add to Netflix Queue

"The only thing that kept me watching License to Wed until the end (apart from being paid to do so) was the faith, perhaps misplaced, that I will not see a worse movie this year."

--A.O. Scott, The New York Times

It starts off like your typical, wedding-themed romantic comedy movie, but then, about 10 minutes in, Robin Williams shows up. As an unconventional pastor (wacky!) who insists on putting an engaged couple (Mandy Moore and The Office's John John Krasinski) through a marriage-prep course of his own devising (zany!) before he'll marry them, Williams is at his obnoxiously hyperactive worst throughout the rest of the film, ruining whatever chance License to Wed had of being a pleasant diversion. That's not to say the film isn't unusually involving for a rom-com; the audience ultimately feels a great deal of sympathy ... for Moore and Krasinski.

12. Because I Said So (2007) Add to Netflix Queue

"It's so derivative, unfunny and thuddingly bad that it's one of the more cringe-inducing movies of a genre chock-full of clunkers."

--Claudia Puig, USA Today

Perhaps the post-Heathers low-point for director Michael Lehmann, Because I Said So wastes the talents of Diane Keaton, Lauren Graham, and Mandy Moore on a story that tries to blend romantic comedy with an exploration of mother-daughter relationships but fails miserably on both counts. Critics and moviegoers found the film's relationships wholly unbelievable, and the script's obsession with orgasms a bit "creepy."

13. The Perfect Man (2005) Add to Netflix Queue

"It's a lame Heather Locklear romantic comedy and a lame Hilary Duff romantic comedy all in one!"

--Luke Y. Thompson, Dallas Observer

It seems almost unfair to have Hilary Duff on this list twice, but, then again, it seems almost unfair to audiences that she keeps making movies. While critics reserved their harshest criticism for the young actress, they certainly didn't spare her co-star Heather Locklear, nor the movie itself -- a lightweight bit of romantic comedy fluff that bored even its intended teen audience.

14. Simply Irresistible (1999) Add to Netflix Queue

"Though glossy and smoothly directed, this limp concoction has all the sparkle of flat champagne."

--Maitland McDonagh, TV Guide

This 1999 flop attempted to blend fantasy, romance, and food a la 1992's Like Water for Chocolate, but the resulting concoction was simply watered-down and all too resistible. Sarah Michelle Gellar stars as an unlikely restaurateur who has crabs (well, just one, but he's magical!), becomes some sort of food witch, and wins the heart of a department store manager. While that may sound oddly interesting on paper, let us assure you: it's not.

15. Sex and the City 2 (2010) Add to Netflix Queue

"We are asked to identify and sympathize with a person who gets everything she wants, but complains anyway."

--John DeVore, Premiere

Well, you probably guessed that this film would show up at some point on this list. And who could blame you? It's hard to know where to begin: the sheer gall of creating an unironic and unaware celebration of materialism and luxury during the worst economic downturn of the last 70 years? Its depiction of Muslim women as both needing to be liberated and needing designer clothes to achieve same? The fact that at one point during the film, these words are uttered: "Lawrence of my labia"? Actually, the movie's biggest sin is even simpler: it has all of the style of a rap video, but none of the plot.

16. Head Over Heels (2001) Add to Netflix Queue

"It's as close to nothing as anything could be while still being something."

--Mick LaSalle, San Francisco Chronicle

The New York Post called it "Rear Window for morons," but it is a Freddie Prinze Jr. movie, so some of that might be redundant. When a young art restorer (Monica Potter) who lives in an apartment full of supermodels witnesses her dreamy neighbor (Prinze) commit a murder, she and her supermodel friends attempt to investigate the crime. The result, naturally, is a wacky romantic comedy filled with low-brow "humor."

17. Crossroads (2002) Add to Netflix Queue

"So vanilla yet so transcendentally sleazy that its target audience seems to be pubescent girls and dirty old priests."

--David Edelstein, Slate

Although we didn't feel that Mariah Carey's infamous Glitter 14 had enough "chick flick" elements to qualify for this list, there's no question that the first big-screen starring role for fellow pop star Britney Spears belongs here. Following three girlfriends on a cross-country road trip after their high school graduation, the critically-panned drama was the first big-studio movie written by Shonda Rhimes, who managed to recover from the experience and create TV hit Grey's Anatomy. Spears, of course, never recovered.

18. The Ugly Truth (2009) Add to Netflix Queue

"In its wan attempt to be raunchy, the picture fails where Judd Apatow has usually succeeded; written by three women, this is a girl's mistaken idea of an R-rated comedy."

--Richard Corliss, Time

Though it made money -- possibly because its raunchier brand of humor pulled in more guys than the typical chick flick -- The Ugly Truth didn't make many fans, especially in the critic community. Katherine Heigl and Gerard Butler are appealing enough as the leads, but this battle-of-the-sexes workplace rom-com certainly lacks the witty banter of classics of the form like Adam's Rib, while its failure to create a strong female protagonist seems far more backwards-looking than that 1949 film.

19. Sweet November (2001) Add to Netflix Queue

"Get out your handkerchiefs. No, scratch that -- get out a pair of windshield wipers and staple them to your brow. Perhaps they'll obscure the screen."

--Marc Savlov, Austin Chronicle

We'll go out on a limb and suggest that Keanu Reeves should avoid dramas. Then again, you wouldn't have films like Sweet November, in which Reeves' performance unintentionally turns a tragic romance into a romantic comedy. A remake of the inconsequential 1968 film of the same name, the second Sweet November is glossier but even more pointless, and it would have taken actors of far greater emotive abilities than Reeves and Charlize Theron to give it any emotional heft other than the superficial response generated by the drawn-out ending.

20. Just Married (2003) Add to Netflix Queue

"Ashton Kutcher and Brittany Murphy are attractive and skilled performers as the film's newlyweds, but the movie is so mechanical it's like watching Barbie and Ken dolls going through the motions."

--Kevin Thomas, Los Angeles Times

It's a January movie, an Ashton Kutcher movie, and a Shawn Levy-directed movie. In our world, that's known as "three strikes." This romantic comedy united Kutcher with then-real-life girlfriend Brittany Murphy as newlyweds on a European honeymoon hoping to finally consummate their marriage, but forgot to bring along a decent script (unless your definition of decent includes many scenes of characters walking into things).

All grosses above are U.S. receipts only. Source for box office data: Box Office Mojo.

What do you think?

Do you want to defend any of the movies listed above? Are there any terrible chick flicks that belong on this list? Let us know in the discussion section below, and check back tomorrow for our look at the best chick flicks of the past 20 years.