Top 10 Chick Flicks Released from 1990-2000

We all watch movies, and which is the “best” is a matter of opinion really. Here are the top 10 chick flicks from 1990-2000. Don’t forget to check out other lists throughout Thought for Your Penny.

10. It Could Happen to You (1994) 71% at Rotten Tomatoes

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Police officer Charlie Lang and his wife Muriel are struggling like everyone else. So much so that one day when he doesn’t have money to tip his waitress at a cafe, he shows her a lottery ticket and promises to split half with her if he wins. When he actually does, his wife leaves him and fights for the full $4 million.

Rating: PG
Director: Andrew Bergman
Starring: Nicolas Cage, Bridget Fonda, Rosie Perez

9. Thelma & Louise (1991) 84% at Rotten Tomatoes

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Friends Thelma and Louise are tired of their dreary lives, so they embark on a road trip. They don’t last long before one of them is sexually assaulted and they find themselves on the run from the police throughout the southern U.S., culminating in an epic scene of sisterhood at the Grand Canyon.

Rating: R
Director: Ridley Scott
Starring: Susan Sarandon, Geena Davis, Harvey Keitel

8. Four Weddings and a Funeral (1994) 95% at Rotten Tomatoes

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British comedy is something you either love or hate, and this subtle comedy follows a group of friends across (you guessed it) four weddings and a funeral. It’s a charming rom-com that captures the peak of its era.

Rating: R
Director: Mike Newell
Starring: Hugh Grant, Andie MacDowell, Kristin Scott Thomas

7. Clueless (1995) 81% at Rotten Tomatoes

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Cher is basically everything you hate about the Kardashians, yet she means well and somehow manages to be endearing. When new girl Tai isn’t fitting in, she gives her a makeover and turns her into a mean girl. It’s a quintessential 90s film that captures everything entitled about the era of malls.

Rating: PG-13
Director: Amy Heckerling
Starring: Alicia Silverstone, Brittany Murphy, Stacy Dash

6. Romy and Michele’s High School Reunion (1997) 70% at Rotten Tomatoes

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Romy and Michele haven’t accomplished much in their lives. It bothers them enough that when they attend their high school reunion in Tucson, AZ, they decide to take a Jaguar from the dealership Romy works at and tell everyone they invented the Post-It note. Their most successful peer, however, is a billionaire who invented a special shoe rubber and actually likes the pair.

Rating: R
Director: David Mirkin
Starring: Lisa Kudrow, Mira Sorvino, Alan Cumming

5. 10 Things I Hate About You (1999) 62% at Rotten Tomatoes

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10 Things I Hate About You is a modern adaptation of Shakespeare’s Taming of the Shrew set in a high school. Bianca Stratford can’t date unless her shrew sister Katarina does, which sets Cameron and Joey on a quest to get Patrick Verona to date Kat so they can go after her sister.

Rating: PG-13
Director: Gil Junger
Starring: Heath Ledger, Joseph Gordon-Levitt, Larisa Olevnik

4. The Wedding Singer (1998) 67% at Rotten Tomatoes

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Robbie Hart is the most sought-after wedding singer in town, but his own relationship ends up on the rocks and he takes a deep dive into depression. That’s when he finds love with Julia, who’s engaged to an asshat of a human being. The race is on to see if they’ll end up together in the end, and there’s a rapping grandma thrown into the mix for good measure.

Rating: PG-13
Director: Frank Coraci
Starring: Adam Sandler, Drew Barrymore, Christine Taylor

3. Reality Bites (1994) 65% at Rotten Tomatoes

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Before Millennials were blamed for being the lazy generation responsible for all the world’s ills, it was Generation X. Lelaina is making a documentary of her Gen-X friends, who are all struggling with the reality of being young slackers who don’t want to work. It’s basically a non-musical Rent.

Rating: PG-13
Director: Ben Stiller
Starring: Winona Ryder, Ethan Hawke, Janeane Garofalo

2. Bridges of Madison County (1995) 89% at Rotten Tomatoes

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When a woman is left alone for a summer by her husband and kids, she has an affair with the first National Geographic writer he comes across. All the man wanted was directions to a bridge in Iowa, and he ends up with a four-day love affair she documents for he kids to find later.

Rating: PG-13
Director: Clint Eastwood
Starring: Clint Eastwood, Meryl Streep, Annie Corley

1. Ever After: A Cinderella Story (1998) 91% at Rotten Tomatoes

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Danielle’s father died, and now she’s stuck as a servant to her stepmother and two stepsisters. When she grows up, she meets the charming Prince Henry, who stole her family’s horse and recovers the Mona Lisa for Leonardo da Vinci. They overcome all odds to live a life happily ever after as royalty.

Rating: PG-13
Director: Andy Tennant
Starring: Drew Barrymore, Anjelica Huston, Dougray Scott

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Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer.

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