19 Underappreciated Chick Flicks

Along Came Polly Jennifer Aniston

Generally, the phrase “chick flick” is used dismissively: a silly piece of fluff or some sentimental claptrap that only girls would like. But it can also mean a movie with strong female leads and a storyline that resonates.

A popular online film forum member recently announced they were “reclaiming” the phrase and asked other members for favorite movies focused on women. Here are 19 top suggestions – and remember, Thelma and Louise was a chick flick!

1. Trainwreck (2014)

Trainwreck LeBron James, Amy Schumer
Image Credit: Universal Pictures.

Amy Schumer's become the butt of many Internet jokes the last several years, but make no mistake, she can make a pretty good movie, with 2014's Trainwreck being a prime example. In the flick, she plays a party girl who must wrestle with her commitment issues and a romance that threatens to change her ways — and make her happy. With assists from Bill Hader and a surprisingly effective LeBron James, this one is a lot of fun. 

2. Friends With Benefits (2011)

Friends with Benefits (2011) Mila Kunis, Justin Timberlake
Image Credit: Sony Pictures Releasing.

Friends With Benefits sees two hyper-attractive folks try to maintain a healthy friendship while hooking up with each other. Of course, this isn't so easy, and their struggle to balance these elements makes for some compelling movie watching. 

3. Along Came Polly (2004)

Along Came Polly Jennifer Aniston
Image Credit: Universal Pictures.

With a quirky script and a star-studded cast composed of Ben Stiller, Jennifer Aniston and Phillip Seymour-Hoffman, Along Came Polly is a certified gem. 

4. How to Lose a Guy in 10 Days (2003)

Matthew McConnaughey and Kate Hudson, How to Lose a Guy in 10 Days.
Image Credit: Everett Collection, Shutterstock.

This one sort of subverted traditional rom-coms by telling a story about actually ruining a romance. The inventive premise, along with strong turns from Kate Hudson and Matthew McConaughey.

5. Stardust (2007)

Claire Danes and Charlie Cox in Stardust (2007)
Image Credit: Paramount Pictures.

Based on Neil Gaiman’s 1999 novel, Stardust is a romantic fantasy-adventure film about a young man who visits the magical world to retrieve a fallen star to give to the woman he loves. Since nothing Neil Gaiman writes is ever that simple, you know going in that the plot will twist and turn.

Its excellent cast includes Claire Danes, Sienna Miller, Charlie Cox, Ricky Jervais, Michelle Pfeiffer, Rupert Everett, and Robert De Niro; Ian McKellen narrates the tale. Some fans say this is a rare case where the movie is better than the book! 

6. Saved! (2004)

Macaulay Culkin, Eva Amurri, Patrick Fugit, Jena Malone, and Mandy Moore in Saved! (2004)
Image Credit: Metro-Goldwyn-Mayer Studios Inc.

This dark, satirical comedy is set at a Christian high school where a group of holier-than-thou girls ostracize a classmate who makes a big mistake. It’s got a whopper of a cast: Mandy Moore, Jena Malone, Macaulay Culkin, Mary-Louise Parker, Patrick Fugit, Heather Matarazzo, and Eva Amurri. One film fan described the movie as “iconic,” and others said they repeatedly quoted one particular Mandy Moore line (which we won’t ruin for you) while in high school. 

The Seattle Post-Intelligencer praised the film’s skilled comic touch and spot-on depiction of teen social dynamics.

7. Ever After (1998)

Ever After Drew Barrymore
Image Credit: 20th Century Studios.

Yet another Cinderella adaptation – but this one is different. Ever After is a romantic period piece that treats the source material as a modern, post-feminist adaptation of the beloved fairy story. Drew Barrymore, Anjelica Huston, Jeanne Moreau, and Dougray Scott star. Several fans swooned over the scene where Barrymore appeared in an extraordinary costume at the ball.

One fan said that even after 100 viewings, the scene hits them in the feels every time; another said they’ve re-watched Ever After more times than any other film.

8. Drop Dead Gorgeous (1999)

Kirsten Dunst Drop Dead Gorgeous
Image Credit: New Line Cinema

Even film fans who don’t like satirical mockumentary black comedies will likely watch this one just for the cast: Kirsten Dunst, Ellen Barkin, Brittany Murphy, Kirstie Alley, Amy Adams (her first film), Denise Richards, Mike McShane, Nora Dunn, Adam West (!), Mo Gaffney, and Allison Janney (who has said she gets more attention from fans for this movie than she ever has for her tenure on The West Wing).

The action occurs in a small town during the annual beauty pageant, where the competition is fierce and the competitors even fiercer. Initially met with mixed reactions, Drop Dead Gorgeous has achieved cult status.

9. Austenland (2013)

Keri Russell, JJ Feild, and Bret McKenzie in Austenland (2013)
Image Credit: Sony Pictures Classics / Giles Keyte.

Some people love the novels of Jane Austen so much that they’ll vacation at a resort that re-creates the Austen era. Keri Russell plays a woman who’s so obsessed with the novels (and the TV adaptations thereof) that she empties her bank account to wear period costumes and act like she lives in a time before indoor plumbing.

One film buff called the movie a delightful piece of camp, and fans note that the supporting cast is excellent – especially JJ Feild, Jennifer Coolidge, Bret McKenzie, and Jane Seymour. 

10. Romy and Michelle’s High-School Reunion (1997)

Mira Sorvino and Lisa Kudrow in Romy and Michele's High School Reunion (1997)
Image Credit: Buena Vista Pictures Distribution.

Lisa Kudrow and Mira Sorvino play Southern California slackers staring down the barrel of their 10-year reunion. They decide to create new personas – successful personas – and show their former bullies a thing or two. Now considered a cult classic, the comedy brings in new generations of fans. One film buff said they loved it as a kid even though the nuance was wasted on them and that it’s still their favorite now that they have enough life experience to appreciate the context of the movie. 

11. Mr. Right (2015)

Sam Rockwell, Anna Kendrick
Image Credit: Focus World.

We’ve all got secrets in our past, right? This one’s a doozy: Martha McKay (Anna Kendrick) finds out her hot new boyfriend (Sam Rockwell) used to be a professional hitman who worked for a government agency. How much of a deal breaker would that be, really? One commenter said they and their husband think the movie’s so romantic that they watch it on Valentine’s Day and their anniversary.

12. Leap Year (2010)

Leap Year Amy Adams, Matthew Goode
Image Credit: Universal Pictures and Optimum Releasing.

Amy Adams plays a woman whose boyfriend (Adam Scott of Parks and Recreation) still hasn’t asked her to marry him after four years together. She takes him to Ireland for leap year day when an old tradition suggests women can propose to their boyfriends. Naturally, nothing goes as planned: lousy weather, cow pies, luggage thieves, and other issues ruin her plans. One commenter called Leap Year their go-to movie whenever they’re feeling glum. It might work for you, too!

13. Heartbreakers (2001)

Jennifer Love Hewitt and Jason Lee in Heartbreakers (2001)
Image Credit: Metro-Goldwyn-Mayer.

Sigourney Weaver and Jennifer Love Hewitt play a mother-daughter con artist team in this romantic crime comedy. One commenter said that Weaver’s skillful acting makes up for much of Hewitt’s lack of experience.

It’s got a great supporting cast, including Ray Liotta, Sarah Silverman, Gene Hackman, Carrie Fisher, Jeffrey Jones, Ricky Jay, Anne Bancroft, Zach Galifianakis, Kevin Nealon, and Nora Dunn. Movie trivia: Heartbreakers was also Anne Bancroft’s last film.

14. Muriel’s Wedding (1994)

Toni Collette in Muriel's Wedding (1994)
Image Credit: Roadshow Entertainment.

The always-thrilling Toni Collette (Hereditary, I’m Thinking of Ending Things, among many others) stars as a socially awkward young Australian who dreams of leaving her dead-end town and creating a glamorous life. It doesn’t go quite as she planned. A commenter who’s apparently Australian said they can’t overemphasize just how “iconic” this comic film is; they claim that one line of dialogue has been used in parliamentary speeches.

A review in Rolling Stone called it “exuberantly funny” and praised Collette’s performance.

15. Music and Lyrics (2007)

Drew Barrymore in Music and Lyrics (2007)
Image Credit: Warner Bros. Pictures.

This fun, romantic comedy concerns a former pop music star (Hugh Grant) and a wannabe writer (Drew Barrymore) who try to compose a song for a pop songstress. Film fans promise you’ll love Grant’s music video, which clearly takes after a real-life ‘80s pop band called Wham! (Remember them?) One commenter said the movie is a good reminder of why women should have better self-esteem when picking boyfriends. 

16. Sugar & Spice (2001)

Marley Shelton in Sugar & Spice (2001)
Image Credit: New Line Cinema.

Some young women will do anything for their girls – including committing armed robbery. The film concerns a high-school cheerleader who gets pregnant and kicked out of her house; her girlfriends help her by staging a few heists. Sound dumb? The late film critic Roger Ebert gave Sugar & Spice three stars, praising its risky premise and saucy nature. Variety called the movie intelligent and satirical. Plus: Cheerleader drama!

17. Boys on the Side (1995)

Drew Barrymore, Whoopi Goldberg, and Mary-Louise Parker in Boys on the Side (1995)
Image Credit: Warner Bros.

Road trip! And with Mary-Louise Park, Whoopi Goldberg, and Drew Barrymore, you know you’re in for a heck of a ride. There’s an undercurrent of danger due to an abusive spouse, some barely suppressed longing, and another chance for Mary-Louise Parker to play a very sick character.

One cinephile admitted the film wrecked them as a teen, but it’s worth another watch. The soundtrack is killer, too, with artists including Joan Armatrading, Bonnie Raitt, The Indigo Girls, Sheryl Crow, Annie Lennox, The Cranberries, Melissa Etheridge, and Stevie Nicks.

18. Now and Then (1995)

Now and Then Christina Ricci Thora Birch Gabby Hoffman Ashleigh Aston Moore
Image Credit: New Line Cinema.

This coming-of-age comedy/drama focused on four women remembering a life-changing summer in their childhood. The outstanding cast includes Christina Ricci, Thora Birch, Gaby Hoffmann, Rita Wilson, Janeane Garofalo, Cloris Leachman, Bonnie Hunt, Melanie Griffith, Hank Azaria, and Rosie O’Donnell.

And it’s not just women plotzing over this chick flick: one commenter outed himself as a dude who loved Now and Then as a kid and has watched it many times.

19. Waitress (2007)

Keri Russell in Waitress (2007)
Image Credit: Fox Searchlight Pictures.

Keri Russell plays a young server in a small town who saves money bit by bit to leave her abusive marriage. That sounds grim, but it’s a comedy-drama with lots of lightheartedness to go with the adversity. One cinephile said they’ve watched Waitress at least half a dozen times, and each viewing is just as good. The superb cast includes the late Adrienne Shelly (who wrote and directed the film), Nathan Fillion, Cheryl Hines, Andy Griffith, and Jeremy Sisto.