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25 Best Chick Flicks Of All Time

25 Best Chick Flicks Of All Time

There are lots of things guys just don’t understand. Good movies is just one example, but who cares? Let them have their car chases and gunslinging shootouts, we’ve got love-at-first-sight and Hugh Grant. Next time you want to have a movie night with the girls, check out one of these 25 classic flicks.

1. 10 Things I Hate About You

This 1999 comedy is based on William Shakespeare’s The Taming of the Shrew, and embraces its origins immediately by making our characters students at Padua High, naming the sweet younger sister Bianca and her older bitter sister Katarina/Kat (Shakespeare’s shrew is Kate). I doubt Shakespeare included a marching band serenade with the song Can’t Take My Eyes Off You in his script, but Heath Ledger sure made it iconic in this adaptation.

25 Best Chick Flicks Of All Time2. To All The Boys I’ve Loved Before

If you are thinking of writing letters to every guy you’ve ever loved, watch this movie first. You may learn a thing or two from Lara Jean Covey.   

25 Best Chick Flicks Of All Time

3. Mean Girls

This 2004 teen comedy is a classic for Gen Z and Millenials. In her effort to take the mean girls down, Cady ends up becoming one of the meanest as she tries to sabotage them from the inside. 

Tina Fey wrote the script so you know it’s hilarious. She even turned it into a Broadway hit in 2018. Keep an eye out for the film adaptation of the musical!

25 Best Chick Flicks Of All Time

4. Legally Blonde

This 2001 comedy has the rare benefit of being a hit with audiences, the box office and critics. It even won the Golden Globe Award for Best Motion Picture: Musical or Comedy and Witherspoon herself was nominated for a Golden Globe and MTV Movie Award.  

Legally Blonde has also been adapted into a Broadway musical. Starting to see a trend here…  

25 Best Chick Flicks Of All Time

5. Clueless

She might be Clueless but, in 1995, Cher Horowitz taught us that even a Beverly Hills life filled with money, fashion, and friends can be wrought with romantic troubles

25 Best Chick Flicks Of All Time

6. Love & Basketball

2000’s Love & Basketball is categorized as a “romantic sports drama film”… a rare category, especially if the athlete is a woman and the story is told mostly from her point of view. It shines a light on what women have to go through personally to be an athlete but, more importantly, it speaks to audiences across race, gender and cultural lines.  

25 Best Chick Flicks Of All Time

7. Bridesmaids

Bridesmaids takes all the drama of being a Maid of Honor to the big screen and Kristen Wiig turns that drama into comedy. Big expenses, crazy bridesmaids and fake-it-til-you-make-it enthusiasm… this 2011 comedy puts the party in these wedding party norms, then adds some raucous hilarity. 

25 Best Chick Flicks Of All Time

8. 4 Weddings And A Funeral

Four Weddings and a Funeral is a 1994 British romantic comedy that follows a circle of friends through that time in their lives when it seems everyone is getting married. Attending these social occasions, they find love, loss and lost loves, along with hilarity and a lesson on getting past the fear of commitment. 

25 Best Chick Flicks Of All Time

9. The Princess Diaries

The Princess Diaries is a 2001 coming-of-age teen comedy that gives hope to all women. Any day now, our Genovian grandmother could show up at our front door to announce we are royalty. Better polish your crown!

25 Best Chick Flicks Of All Time

10. Pitch Perfect

Pitch Perfect hit the scene in 2012 to let all misfits know that they are one a capella group away from greatness. With a cast of hilarious and quirky characters, this flick danced, sang, and beat-boxed its way into our hearts and onto our list. 

25 Best Chick Flicks Of All Time

  1. 16 Candles

Mr. or Ms. Right feels way out of your league and those pursuing you seem 100% wrong. 16 Candles strikes this all too familiar nerve for audiences across the decades. That, along with its hilarious depiction of high school social classes, has helped this 1984 teen comedy stand the test of time. 

The styles and songs of 1980’s pop culture make this teen love story feel like a trip in a time machine…as do some more sobering realities. Like many other movies of that era, modern audiences will recognize #MeToo moments  and racial stereoptyping that are outright wrong. Lots of things made it onto the big screen in the ’80s and became “iconic,” when the same content would raise red flags and a media hailstorm if it was produced today. That doesn’t mean you can’t still watch and even enjoy the good parts of 16 Candles–just make sure to think critically, and know that just because something is a “classic,” doesn’t mean it’s right.

25 Best Chick Flicks Of All Time

12. Pretty Woman

We all love a good Cinderella story, but a film named Pretty Woman whose main character is a prostitute sounds pretty misogynistic, not like something that would make our list. But while Julia Roberts in her prime was more than pretty, it was her character’s wit, confidence, and authenticity that made her irresistible. 

Love story aside, the shopping scene alone might be what makes this a female fave. Who hasn’t dreamed of being given carte blanche with a credit card and instructions from a millionaire to be spoiled rotten on Rodeo Drive? Or maybe it’s because this 1990 romantic comedy flipped Hollywood’s definition of intimacy. As a professional sex worker, Vivan has a strict no-kiss policy for clients. So when she and Richard do kiss, it out-smolders the rest of the bedroom scenes. 

25 Best Chick Flicks Of All Time

13. The Notebook

The Notebook is the romantic drama of all romantic dramas. The chemistry between Ryan Gosling and Rachel McAdams as a young couple who fall in love in the 1940s rocked female audiences in 2004 and it still does today. Entertainment Weekly credited the pair for the Best Movie Kiss of All Time and I’m crediting Nicholas Sparks with one of the all-time sweetest plot twists. Who knew a nursing home romance could become every girl’s #lifegoals? I’m just a sucker for old people in love. 

25 Best Chick Flicks Of All Time

14. Bridget Jones’ Diary

Thirty-something Bridget Jones has committed herself to find love within the year and is keeping a diary to chronicle her experience. This may feel oddly familiar to some, along with Bridget’s frustrations with nosy family members. Yet this romantic comedy is as original as it is funny. Bridget’s imperfections are what make her irresistible to watch… smoking and binge drinking with her quirky friends, struggling with her weight, and seducing her dream guy (who just happens to be her boss).   

25 Best Chick Flicks Of All Time

15. Mamma Mia!

This 2008 film adaptation of the musical is a 108-minute-long dance party. A young bride-to-be is determined to have her dad walk her down the aisle at her upcoming wedding, but she doesn’t know who her dad is. She solves the problem by inviting all three possible paternal matches and the antics ensue as the dynamic cast sings and dances its way through a collection of songs by the 1970’s group, ABBA. Seeing Meryl Streep as the lead singer of Donna and the Dynamos is reason enough for women to appreciate this picture.

25 Best Chick Flicks Of All Time

16. The Devil Wears Prada

We find Meryl Streep in another famous chick flick,The Devil Wears Prada, and, this time, her character, Miranda Priestly, is a witch with a capital “B”. Her jaw-dropping wickedness and wit make us love to hate her and, secretly, we may just want to be her (at least until we get to the second half of the movie). The Devil Wears Prada is as fresh a film as it was in 2006 due to its countless memorable moments and one-liners, masterful performances from Anne Hathaway, Emily Blunt and Stanley Tucci and designer duds so impressive, they could have been nominated for their supporting role in the production.

25 Best Chick Flicks Of All Time

See Also

17. Love, Actually

Clever, hilarious and romantic, Love Actually is a 2003 Christmas comedy that has hit many favorite flick lists for good reason. First of all, it features Hugh Grant and, as any romantic comedy lover knows, Hugh Grant always equals chick flick. But, this time, Hugh is not the only leading man. There are several in this ensemble cast featuring ten distinct love stories that become intertwined as the plot progresses. Each of these mini-plots is unique, not only from one another, but also from the typical romantic storylines that get played out time and again in blockbuster hits. Just like in true love, you really don’t know what to expect next (unless you are re-watching it, again, as a Christmas tradition like so many others).  

25 Best Chick Flicks Of All Time19. Titanic

Winner of 11 Academy Awards, including Best Picture, Titanic is considered an epic motion picture masterpiece portraying an infamous historic moment, but that doesn’t make it a chick flick. What garners this1997 film a spot on our list and in the hearts of so many of our gal pals is the forbidden love story of Rose and Jack, Leonardo di Caprio’s cool portrayal of this refreshingly fun-loving guy and the romantic way he stole her heart from her rich, abusive jackwagon of a fiance. In fact, women love their love enough to overlook Rose’s crazy decision to throw the Heart of the Ocean blue diamond away. Why, Rose, why???

25 Best Chick Flicks Of All Time

19. The Proposal

Maybe it’s the chemistry between Sandra Bullock and Ryan Reynolds. Maybe because women enjoy seeing the modern reversal of roles with Bullock as the high-powered business exec and Reynolds as the assistant. Or maybe it’s just that the real world can get complicated and scary, and a cute, predictable, onscreen romance can feel like just the cheap escape we need.  

25 Best Chick Flicks Of All Time

20. He’s Just Not That Into You

He’s Just Not That Into You is another one of those multi-story romantic comedies showing a web of love stories but, in this 2009 flick, the love is hard to find. You’ll laugh. You’ll cry. You’ll recognize some of your friends, and maybe even a bit of yourself, in the onscreen characters. 

25 Best Chick Flicks Of All Time

21. She’s The Man

Yet another Shakespeare adaptation set in a high school, She’s The Man is one of my personal favorites. It’s a quirky remix of Twelfth Night that explores the humor to be found in a girl disguising herself as a boy, instead of the established (and often demeaning and transphobic) trope of having a man dress up as a woman for laughs. I also love its focus on female athletes and the empowering importance of sports for high school girls. It’s a funny, romantic movie that reminds us that girls can be rough and love sports, and boys can be sensitive and squeal when they see spiders.

25 Best Chick Flicks Of All Time22. Breakfast At Tiffany’s

Breakfast at Tiffany’s is a true classic and the timeless Audrey Hebburn continues to capture the attention and imagination of women today. In this 1961 romantic comedy, Hepburn dazzles audiences with her charm and beauty as a young New York socialite. 

However, this is another older movie with serious flaws that can’t be brushed aside. Mickey Rooney plays an Asian character, which is in itself a problem, and that character is pretty much just a racist stereotype intended for comic relief. 

25 Best Chick Flicks Of All Time

23. You Again

Getting even with your high school bully gets a lot harder when that bully is about to marry your brother. Multiple generations of rivals duke it out in this wedding comedy that’s hilarious fun for the whole family.  With a star-studded cast of longtime female actress favorites–Kristen Bell, Jamie Lee Curtis, Sigourney Weaver, Kristin Chenowith, and the iconic, immortal Betty White–this 2010 comedy checks all the boxes. (And just wait until you see the ending!)

25 Best Chick Flicks Of All Time24. When Harry Met Sally

“Can men and women ever just be friends?” While countless of us would answer with a wholehearted, “YES!”, it’s a question romcoms through the ages can’t get enough of asking, and one this romantic comedy tackled back in 1989. As we followed Harry and Sally through twelve years of chance encounters and levels of relationship, these hilarious characters left their mark on society with phrases like “high-maintenance” and “transitional person” that live on as everyday mainstays in relationship conversations today, not to mention the hysterically iconic deli scene and punchline The New York Times called “one of the most memorably funny lines in movie history”.

25 Best Chick Flicks Of All Time25. The Parent Trap

Sometimes, girls just wanna have good, clean fun, and Disney delivers with 1998’s The Parent Trap. It’s a remake of the 1961 film with the same story, but this one has Lindsay Lohan when she was young and innocent, and it’s the go-to feel-good movie for ’90s and ‘2000s girls.

25 Best Chick Flicks Of All Time

What’s your favorite chick flick? Share it in the comments and we’ll put it on our watch list!

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