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Best 11 Chick Flicks of the 90s: Must-Watch Romantic Movies in 2023

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The 1990s was an absolutely amazing decade that not only introduced us to the enchanting world of Harry Potter but also brought us some incredibly enjoyable chick flicks. This super cool list of the best ’90s chick flick movies offers a mix of hilarious comedies and heartfelt dramas, with a sprinkle of dramedies like Pretty Woman and While You Were Sleeping. And if you’re looking for a good laugh, you absolutely can’t miss French Kiss.

Prepare to spot some famous faces on this list, as it showcases celebrities who skyrocketed to fame in the groovy nineties, including the one and only Leonardo DiCaprio, the lovely Brittany Murphy, the stunning Angelina Jolie, and the fabulous Alicia Silverstone. Alongside these talented actors and actresses, you’ll find some timeless classics like Titanic, Clueless, and Girl Interrupted.

No matter what kind of mood you’re in, this list has the perfect ’90s chick flick for you. But choosing the ultimate best of the ’90s is a real challenge, because there are so many incredible options.

Now, let’s dive into a discussion about your personal favorites from the nineties. The truth is, you don’t have to limit yourself to just one! You have the incredible power to celebrate all your beloved 1990s chick flicks and even share your not-so-favorite ones.

So, which chick flicks from the ’90s hold a special place in your heart? We can’t wait to hear from you and join the totally awesome conversation!

1. Clueless

Set in the heart of Beverly Hills, Clueless follows the story of high schooler Cher Horowitz (Alicia Silverstone), who proudly claims the title of a fashionista and matchmaker. Directed by Amy Heckerling, this comedy-drama flick delves into Cher’s journey through adolescence, as she navigates the challenges of love and strives to maintain her social status. Cher’s partner in crime is her best friend Dionne Davenport (Stacey Dash), who joins her in all sorts of adventures. Drawing inspiration from Jane Austen’s Emma, the film brilliantly captures the emotions and complexities of teenage life. And while it maintains a lighthearted tone, it subtly addresses important social issues, ensuring its status as a timeless classic.

Released: 1995
Directed by: Amy Heckerling
Actors: Alicia Silverstone, Stacey Dash, Brittany Murphy

2. 10 Things I Hate About You

10 Things I Hate About You
Welcome to 10 Things I Hate About You, a modern twist on Shakespeare that combines teenage romance with biting comedy. It’s set in an American high school and centers around two sisters, Kat and Bianca Stratford. Kat is rebellious and played by Julia Stiles, while Bianca is popular and portrayed by Larisa Oleynik. The story kicks off when Cameron, a new student who’s smitten with Bianca, discovers their father’s strict dating rule. Determined to win her over, Cameron devises a plan involving the bad boy Patrick Verona, played by Heath Ledger, to charm Kat. As the plot unfolds, witty banter and unexpected romances take center stage as the characters navigate the complexities of teenage angst, love, and self-discovery. This film is known for its memorable performances and sharp humor, making it a delightful exploration of young love and personal growth.

Released: 1999
Directed by: Gil Junger
Actors: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt

3. A League of Their Own

A League of Their Own
In the heart of World War II, there’s this awesome movie called A League of Their Own. It’s a comedy-drama directed by Penny Marshall and is filled with historical significance and a bit of humor. The story follows two sisters, Dottie Hinson (played by Geena Davis) and Kit Keller (played by Lori Petty), from Oregon who are recruited to play in the All-American Girls Professional Baseball League. This league was put together because all the male baseball players got drafted into the war.

Their coach, Jimmy Dugan (played by Tom Hanks), is a bit of a boozer, but he’s also there to guide them. Together, they and their teammates face all kinds of challenges as they try to keep the league going. They have to deal with society’s expectations and their own personal conflicts. It’s a real struggle, but their journey ends up changing the way people think about women in sports and society. They shatter stereotypes left and right.

And let me tell you, this movie is a classic! It gives you a glimpse into a really important part of American history. It’s definitely worth a watch.

Released: 1992
Directed by: Penny Marshall
Actors: Tom Hanks, Geena Davis, Madonna

4. Titanic

The 1997 epic romance-disaster film Titanic tells the story of Jack Dawson (played by Leonardo DiCaprio), a struggling artist, and Rose Dewitt-Bukater (played by Kate Winslet), a young woman from a wealthy background. They meet on the ill-fated R.M.S. Titanic and their unlikely friendship blossoms into a beautiful love story, despite their different social statuses. James Cameron directed this film, skillfully weaving their personal journey with the historical events of the ship’s tragic maiden voyage. Titanic received a staggering 11 Academy Awards, including the prestigious Best Picture and Best Director, solidifying its status as a monumental cinematic achievement. Even today, Titanic serves as a powerful reminder of the indomitable human spirit in the face of disaster.

Released: 1997
Directed by: James Cameron
Actors: Leonardo DiCaprio, Kate Winslet, Billy Zane

5. She’s All That

She's All That
She’s All That, released in 1999, is a fun romantic comedy directed by Robert Iscove. It tells the story of Zack Siler, a popular high school jock played by Freddie Prinze Jr., who gets dumped by his girlfriend. In an attempt to prove himself, Zack makes a bet with his friends that he can transform any girl into the prom queen within six weeks. That’s when he sets his sights on Laney Boggs, an introverted art student portrayed by Rachael Leigh Cook.

Throughout the film, we see Zack facing various challenges as he tries to make Laney the queen of the prom. But as he spends more time with her, unexpected emotions start to arise. This light-hearted movie explores different themes such as popularity, staying true to oneself, and the unpredictable nature of love in the high school environment. It’s a delightful watch that brings a fresh and entertaining take on teenage romance.

Released: 1999
Directed by: Robert Iscove
Actors: Freddie Prinze, Rachael Leigh Cook, Matthew Lillard

6. You’ve Got Mail

You've Got Mail
In the romantic comedy You’ve Got Mail, we meet Kathleen Kelly, played by the lovely Meg Ryan. She’s a charming bookstore owner in the heart of New York City. One day, she stumbles upon an anonymous pen pal online and can’t help but fall head over heels for this mystery person. Little does she know, her online love interest is none other than her business rival, Joe Fox, played by the talented Tom Hanks. Joe is the owner of a massive bookselling chain, and the two have quite the rivalry going on.

Amidst the hustle and bustle of the Big Apple, Kathleen and Joe’s digital love story unfolds. It’s a classic tale of love in the age of the internet, where identities can be hidden behind screens. But here’s the twist: their online connection starts to affect their real-life animosity towards each other. Can you believe it?

Directed by the talented Nora Ephron, this delightful film explores themes of modern romance and the complexities of identity in the digital era. With its heartwarming story and the chemistry between Meg Ryan and Tom Hanks, You’ve Got Mail is a must-watch for any rom-com fan.

Released: 1998
Directed by: Nora Ephron
Actors: Tom Hanks, Meg Ryan, Parker Posey

7. Sleepless in Seattle

Sleepless in Seattle
In Sleepless in Seattle, we follow the story of Sam Baldwin (played by Tom Hanks), a widower who catches the attention of the nation when his son Jonah (played by Ross Malinger) calls into a radio talk show. Little did they know that this simple act would set in motion a chain of events that would bring Sam into the life of Annie Reed, a journalist portrayed by Meg Ryan. Annie, upon hearing Sam’s touching tale, finds herself drawn to him in a curious way.

What follows is a delightful twist of fate, as Sam and Annie’s paths intersect in a momentous encounter at the iconic Empire State Building. Directed by the talented Nora Ephron, this romantic drama has been recognized with two Oscar nominations and is widely praised for its unique blend of comedy and heartfelt emotion. It truly captures the essence of love surpassing all boundaries.

Released: 1993
Directed by: Nora Ephron
Actors: Tom Hanks, Meg Ryan, Bill Pullman

8. Never Been Kissed

Never Been Kissed
In the rom-com Never Been Kissed, we meet Josie Geller (played by the lovely Drew Barrymore). She’s not your average Chicago Sun-Times copy editor, as she dreams of something bigger than her tiny cubicle. So, when she’s given the opportunity to go undercover in a high school and write about modern teenage life, she jumps at the chance, despite having a not-so-pleasant high school experience herself.

During her undercover mission, Josie unexpectedly crosses paths with Sam Coulson (played by the charming Michael Vartan), who happens to be an English teacher. And as you might have guessed, romantic sparks start to fly between them. As Josie tries to juggle her assignment and her newfound feelings, we get to witness a beautiful tale of self-discovery and first love unfold on the screen.

This film, with its witty humor and delightful charm, takes us back to the sometimes rocky waters of high school life and love. It’s a heartfelt story that will make you laugh, swoon, and reminisce about your own teenage years.

Released: 1999
Directed by: Raja Gosnell
Actors: Drew Barrymore, David Arquette, Michael Vartan

9. Cruel Intentions

Cruel Intentions
In the captivating drama, Cruel Intentions, we are immersed in the world of Manhattan’s elite teenage circle. Kathryn Merteuil (played by the talented Sarah Michelle Gellar) and Sebastian Valmont (portrayed by the charismatic Ryan Phillippe) are step-siblings notorious for their manipulative ways. Their attention is now focused on the unsuspecting Annette Hargrove (brought to life by Reese Witherspoon).

As the story unfolds, Sebastian initially sees Annette as a conquest, someone to add to his long list of triumphs. However, things take an unexpected turn as he finds himself caught in a web of complex emotions. This film, a modern adaptation of the timeless French novel ‘Les Liaisons dangereuses’, delves into the themes of deceit, love, and the intense dynamics of teenage power games.

Cruel Intentions offers a thrilling exploration of manipulation, cleverly hidden behind the facade of youth and wealth. It takes us on a journey where innocence and ambition collide, leaving us on the edge of our seats, eager to discover what lies beneath the surface of this mesmerizing tale.

Released: 1999
Directed by: Roger Kumble
Actors: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon

10. Notting Hill

Notting Hill
Notting Hill is a charming romantic comedy that takes place in London’s picturesque Notting Hill district. The story revolves around William Thacker, a humble bookstore owner, and Anna Scott, a famous American actress. These two unlikely characters cross paths in William’s shop, setting off a series of events that combine the ordinary with the extravagant. As their lives become entwined, they face the difficulties of fame, privacy, and, of course, love. Directed by Roger Michell, this film is a delightful exploration of how two very different lives can come together in the most unexpected of locations.

Released: 1999
Directed by: Roger Michell
Actors: Julia Roberts, Hugh Grant, Hugh Bonneville

11. Pretty Woman

Pretty Woman
In the classic rom-com Pretty Woman, we witness an unlikely love story between Edward Lewis, a wealthy businessman played by Richard Gere, and Vivian Ward, a spirited and street-smart woman portrayed by Julia Roberts. Their paths cross unexpectedly, and they must navigate the challenges that arise from their contrasting lifestyles. As their connection deepens, the boundaries between business and pleasure become hazy, leading to heartfelt revelations. Garry Marshall skillfully directs this film, which is celebrated for its clever dialogue and impressive performances. Julia Roberts, in particular, delivers a captivating portrayal of Vivian that garnered her an Oscar nomination.

Released: 1990
Directed by: Garry Marshall
Actors: Richard Gere, Julia Roberts, Ralph Bellamy

Michael Bennett
Michael Bennett
With over 5 years of experience, Michael Bennett is an experienced entertainment blogger recognized for straightforward reviews. His research expertise and thoughtfully crafted blog posts make him a source for readers seeking movie and tv show recommendations.


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