The 25 Best Chick Flicks of All Time

With three sisters and lots of girl friends, I’ve watched my fair share of chick flicks. And I love them! Yes, I love the predictable endings, the cheesy lines, and the carbon copy plot twists from movie to movie. Why? Because I also love the recurring actresses (who doesn’t love a good Aniston movie), the pretty settings, and the romance of course! Now there are a LOT of chick flicks out there, some are sweet and funny, and others, not so much. Here are my 25 favorite chick flicks, from the 1990’s to now (not in order, mainly because I couldn’t decide on a favorite)!

25 Chick Flicks Every Girl Must See

1. Something Borrowed (2011)

25 Best Chick Flicks of all Time: Something Borrowed

Why: the adorable Ginnifer Goodwin and a very bitchy and detestable Kate Hudson.

 

 

 

 

 

2. 10 Things I Hate about You (1999)

25 Best Chick Flicks of all Time: 10 things I Hate about You

Why: the Kat-Bianca dynamic, a young and very romantic Joseph Gordon-Levitt, the 90’s angry chick soundtrack, and Heath Ledger.

 

 

 

 

 

3. Heartbreakers (2001)

25 Best Chick Flicks of all Time: Heartbreakers

Why: Sigourney Weaver singing Russian karaoke, Sigourney Weaver with a Russian accent, Sigourney Weaver just generally being amazingly funny.

 

 

 

 

4. Love Actually (2003)

25 Best Chick Flicks of all Time: Love actually

Why: it’s THE pioneer in the now very famous and slightly over-used multiple-connecting-romantic-plot-lines genre, it has an amazing cast, all the love stories are adorable, and it also focuses on family stories.

 

 

 

 

5. She’s All That (1998)

25 Best Chick Flicks of all Time: she's all that

Why : the 90’s outfits and hairstyles, obscenely rich and idiotic high-schoolers, a taco-shaped hat, and a sweet Freddie Prince Jr in over his head. And, everyone loves a good makeover.

 

 

 

 

6. 13 Going on 30 (2004)

25 Best Chick Flicks of all Time: 13 Going on 30

Why : Jennifer Garner is perfect as a nerdy, clumsy 13-year old discovering the city, clothes and makeup and men.

 

 

 

 

7. 50 First Dates (2004)

25 Best Chick Flicks of all Time: 50 first dates

Why : Adam Sandler in an emotional, romantic and still very funny role, a Hawaiian setting, and the amazing Drew Barrymore.

 

 

 

 

 8. He’s Just Not That Into You (2009)

25 Best Chick Flicks of all Time: he's just not that into you

Why : an enjoyable Love Actually-esque movie, with an incredible cast. And again, Ginnifer Goodwin.

 

 

 

 

 

9. Time Traveller’s Wife (2009)

25 Best Chick Flicks of all Time: Time Traveler's Wife

Why : clearly, Rachel McAdams.

 

 

 

 

 

10. Just Like Heaven (2005)

25 Best Chick Flicks of all Time: Just Like Heaven

Why: a bit of an “Idiot Plot”, but the dialogue in this movie is very sweet, and from the first scene you realize these two are exactly what the other needs and you’re hooked.

 

 

 

 

11. The Girl Next Door (2004)

25 Best Chick Flicks of all Time: The Girl Next Door

Why : Emile completely stoned at a scholarship dinner, an impromptu porn movie shoot, two hilarious and perverted best friends, actual plot twists, funny dirty hallucinations, and the very endearing Elisha.

 

 

 

 

12. 27 Dresses (2008)

25 Best Chick Flicks of all Time: 27 Dresses

Why: the Bennie and the Jets scene, hilariously ugly bridesmaid dresses, and James Marsden.

 

 

 

 

 

13. Life as We Know it (2010)

25 Best Chick Flicks of all Time: Life as we Know it

Why : an unbelievably cute baby (called Sophie!), actual plot twists, a very cute and realistic dynamic between the two characters, and an original plot for a chick flick. This one is in my top three.

 

 

 

14. In her Shoes (2005)

25 Best Chick Flicks of all Time: In Her Shoes

Why: a hilarious Cameron Diaz and very funny and relatable sibling rivalry.

 

 

 

 

15. There’s Something about Mary (1998)

25 Best Chick Flicks of all Time: something about mary

Why: featuring so many iconic scenes like the zipper, fishing hook, dog resuscitation and hair gel malfunctions, this movie is just too funny to miss.

 

 

 

 

16. Never Been Kissed (1999)

25 Best Chick Flicks of all Time: never been kissed

Why: a feel-good movie about a nerdy teenager finally getting revenge on the world, complete with 90’s hair and outfits, and a gool ol’ makeover.

 

 

 

 

17. Crazy Stupid Love (2011)

25 Best Chick Flicks of all Time: crazy stupid love

Why: Emma Stone and Steve Carrell at the top of their game, an adorable middle school boy with a crush on his babysitter, an endearing player-turned-romantic Ryan Gosling, and a absolutely hilarious big reveal at the end.

 

 

 

 

18. Where the Heart is (2000)

25 Best Chick Flicks of all Time: Where the Heart is

Why: the beautiful and extremely talented Natalie Portman, a cute librarian, the quirky Walmart setting, weird baby names like Americus and Praline, incredible characters, and a grown-up Channing Stockard.

 

 

 

 

19. Marley & Me (2008)

25 Best Chick Flicks of all Time: Marley & Me

Why: the world’s craziest yet cutest dog, Aniston of course, really pretty houses, and a very cute and relatable couple.

 

 

 

 

 

20. John Tucker Must Die (2006)

25 Best Chick Flicks of all Time: John Tucker Must Die

Why: an extremely bitchy Sophia Bush, basketball players in thongs, a good soundtrack, and girl power at its best. Even Ashanti can’t make this movie bad.

 

 

 

 

21. Mean Girls (2004)

25 Best Chick Flicks of all Time: Mean Girls

Why: because Tina Fey is quite simply a genius.

 

 

 

 

22. The Notebook (2004)

25 Best Chick Flicks of all Time: The Notebook

Why: an adorable teenage summer romance,a very endearing older couple, Ryan Gosling and James Marsden in the same movie, the very steamy now iconic kiss scene, a beautiful Southern setting, and Rachel McAdam’s 1940’s outfits and hair.

 

 

 

 

23. The Lake House (2006)

25 Best Chick Flicks of all Time: Lake house

Why: a different take on a time-centric plot, a beautiful house, a very cute dog, infuriatingly close calls, and very likable characters (even Keanu).

 

 

 

 

 24. The Holiday (2006)

25 Best Chick Flicks of all Time: The Holiday

Why: An amazing cast, a very likeable and not-too-silly Jack Black, an amazing LA house and cute British cottage, a very funny Cameron Diaz, Jude Law’s adorable daughters, a sweet Kate Winslet helping her elderly famous neighbor, and the holiday spirit.

 

 

 

 

25. Easy A (2010)

25 Best Chick Flicks of all Time: Easy A

Last but certainly not least.

Why : Emma Stone is absolutely hilarious, two quirky parents, the “Pocket of Sunshine” singing scene, a completely crazy Lisa Kudrow and Amanda Bynes, and an original plot.