The 100 Best Chick Flicks Of All Time

If there’s anything we know and understand, it’s chick flicks. The good, the bad, the ugly- we’ve seen ’em all…and we’ll see ’em again. Perfect for girls’ night, a rainy day solo on the couch, or even for a cuddle sesh with bae; here are 100 of the best chick flicks of all time. (And yes, they are in alphabetical order- ranking this collection of chick flicks would have been WAY too hard!)

1. 10 Things I hate About You

Because who doesn’t love a bad boy? Especially when it’s Heath Ledger.

2. 13 Going On 30

Bring out your inner child, no matter what age. Mark Ruffalo and Jennifer Garner are unforgettable.

3. 17 Again

Or teenager. Do you ever wish you had another chance? Relive high school with this chick flick!

4. 27 Dresses

Always a bridesmaid, never a bride- so relatable. This is the perfect movie to get in the mood for wedding season.

5. 500 Days of Summer

Summa lovin’. Classic guy falls for girl story. Joseph Gordon Levitt and Zoey Deschanel are the cutest hipsters.

6. A Cinderella Story

The tragic moment when Lizzie McGuire started to grow up. This is the perfect movie to watch around Halloween!

7. A Lot Like Love

When things are meant to be, they’re meant to be. You never know who you’ll meet on an airplane.

8. A Walk to Remember

Sometimes true love can be found doing community service! Do yourself a favor, have the tissue box handy for this one!

9. America’s Sweethearts

You never know what can happen when movie stars break up! Who doesn’t love a love story with a few twist and turns?

10. Breakfast at Tiffany’s

Anything with Audrey Hepburn is an instant chick flicks classic. Do yourself a favor and watch this now!

11. Bride Wars

Every girl’s worst nightmare. Kate Hudson and Anne Hathaway are great together, even when they’re against each other.

12. Bridesmaids

What goes better together than love and comedy?  Everyone wants to be the maid of honor.

13. Bridget Jones’ Diary

Maybe your diary can become a movie too. Who doesn’t love Hugh Grant? Must be the accent.

14. Bring It On

Bring it… another classic high school chick flick.

15. Center Stage

If you ever tried ballet, this is the movie for you. Guys wearing leotards? Sign us up!

16. Charlie St. Cloud

Once brothers, always brothers. In case you’re in the mood for another tearjerker. Zac Efron delivers.

17. Clueless

As if! Before Mean Girls existed, the struggle for popularity in high school is real.

18. Coyote Ugly

For any songwriter who ever had to work in a restaurant or bar, this will hit home with a twist of comedy. Did anyone else want to be a Coyote Ugly girl after this one?

19. Crazy, Stupid, Love

Ryan. Gosling. ‘Nuff said. But really, this one will have you laughing the whole time. Divorce, new relationships, hooking up, young love, it has it all!

20. Crossroads

Brit’s good ole days. Maybe it will inspire you to take a road trip with your best friends!

21. Dear John

Again with the tears. Who doesn’t love a chick flick with Channing Tatum?

22. Definitely, Maybe

Flashbacks and reminiscing. What more could you want? Ryan Reynold’s character gets advice on love from his 11 year old, definitely a family fun comedy for any ocassion.

23. Dirty Dancing

Oh Patrick Swayze, the very first bad boy who stole our hearts in this memorable chick flick. We all know you tried to re-enact some of these scenes.

24. Divine Secrets of the Ya-Ya Sisterhood

You never know what you can learn by scrapbooking! The ultimate #girlsnight flick. Break out the popcorn and enjoy.

25. Drive Me Crazy

We all know what trying to find a date to the prom is like, but what happens when your date cancels? Who can forget Melissa Joan Heart? I’m still not so sure how I feel about the ending…

26. Ever After

Another Cinderella story to warm your heart. Who doesn’t love Drew Berrymore? We all love a movie that ends with happily ever after.

27. Failure to Launch

Cute and quirky and Mathew McConaughey. You don’t want to be living with your parents in your thirties.

28. Freaky Friday

Have you ever thought about switching places with your mom? Whether the old one or the new one, this one’s a favorite amongst the ladies.

29. Friends with Benefits

The epitome of chick flicks. Hot actors, a typical romcom story line and a happy, sappy ending.

30. Girls Just Wanna Have Fun

Another goodie for a gals’ night in. Like the song, this is a classic. Also, see Sarah Jessica Parker way before Sex and the City.

31. Gone with the Wind

Classic. This is one you can watch over and over again through the years. Whether you’re looking for a chick flick, or an overall classic, you can’t go wrong.

32. He’s Just Not That Into You

*Cringe* Everyone can relate to this one (whether you want to admit it or not).

33. How to Lose a Guy in 10 Days

Seriously, if this isn’t on the top of everyone’s list of best chick flicks, I don’t know what would be. Kate Hudson and Matthew McConaughey are the best duo.

34. In Good Company

A cute one…oh, the movie’s okay too. (Yes, I’m referring to Topher Grace.)

35. In Her Shoes

No one knows how to bring sisters together like a grandmother… that you never knew you had. A good one for some sisterly love. This will have you bonding.

36. John Tucker Must Die

You always have to watch out for the new girl in town. Where is Jesse Metcalf these days?

37. Josie and the Pussycats

If you’re in the mood for a sing-a-long. This should be your go to.

38. Legally Blonde

Sure, a bit ditzy- but #girlpower, am I right? Who hasn’t quoted this classic Reese Witherspoon chick flick? Have you ever followed your ex? You should definitely watch this if you’re thinking about law school.

39. Letters to Juliet

Guys, it’s about love letters. A modern twist on the timeless classic.

40. Little Black Book

Never look through your friends phone… unless you’re really curious. This is when Brittany Murphy proved she was made for chick flicks.

41. Little Women

One of our childhood favorites! Do yourself a favor and give the book a shot before you watch this one. Winona Ryder never disappoints.

42. Love Actually

Nothing really needs to be said here, but you should definitely watch it around the holidays!

43. Love and Basketball

Seductive. Sports. Sex. It’s got it all. You’ll want to play a game of horse after this one.

44. Love and Other Drugs

An emotional roller coaster definitely worth a watch. Anne Hathaway and Jake Gyllenhaal kill it.

45. Made of Honor

You know how it’s going to end right from the very beginning, but it’s always nice watching Patrick Dempsey on the big screen.

46. Maid in Manhattan

If you can make it there, you can make it anywhere. Jennifer Lopez always gets the man. (I mean, who could say no to J.Lo?!)

47. Mamma Mia

Get ready to bust out some tunes. “Here I go again!”

48. Mean Girls

If you haven’t already watched this… well you’ve heard the quotes. Chick flicks don’t always have to revolve around romance. See Lindsay Lohan in her glory days.

49. Miss Congeniality

Cute and comical. See Sandra Bullock go undercover as Miss America contestant!

50. Moonstruck

If you’re looking for an oldie but a goodie, this one’s for you.

51. My Best Friend’s Wedding

Falling in love with your best friend might not be the best idea. Just saying.

52. My Big Fat Greek Wedding

Awkward in all the right ways. A classic comedy and chick flick.

53. Mystic Pizza

A great coming-of-age story! Sean Penn will have you in tears. Watch this with your childhood friends.

54. Never Been Kissed

Never gets old. Drew Berrymore is awkwardly cute. We all had that phase, you never forget your first kiss.

55. No Strings Attached

Another one of those typical chick flicks…that we’ll watch every single time it’s on.

56. Notting Hill

We all wish we were dating a movie star. Another Hugh Grant classic…that accent though.

57. Now and Then

If you haven’t seen this movie, stop what you’re doing and watch it right now!

58. P.S. I Love You

This one will tug at your heartstrings. Gerard Butler and his letters, the best.

59. Picture Perfect

I wouldn’t recommend pretending to be engaged. Old school Jennifer Aniston, absolutely hilarious.

60. Pitch Perfect

Always good for a quick pick-me-up. And the music- stellar. See Jimmy Fallon before he was on TV every night.

61. Pretty in Pink

When in doubt, break out this classic! You will not be dissappointed.

62. Pretty Woman

Richard Gere and Julia Roberts star in the most unlikely love affair. Goes to show you it doesn’t matter what two people do to make a living, they can find love.

63. Romeo and Juliet

What’s more romantic than Romeo and Juliet? Nothing. The answer is nothing. Whether you like Shakespeare or not, everyone has to see this chick flick.

64. Romy and Michele’s High School Reunion

Perfect for the BFFs. This will get you pumped for your reunion!

65. Runaway Bride

Not how you expect the traditional chick flick to go! Let’s just hope this doesn’t happen to any of us.

66. Save the Last Dance

Love knows no boundaries. The moves are unforegettable and you’ll be trying them out yourself.

67. Serendipity

If you believe that everything happens for a reason, this will only confirm that thought.

See Also

68. She’s All That

Oh high school love, confusing and timeless. Watch the high school hot shot battle with the underdog.

69. Sisterhood of the Traveling Pants

Another girls’ night essential. If you haven’t read the book, you should. Watch this with your friends who forget to give you back your clothes you lent them.

70. Sixteen Candles

Sixteen is a rough age for everyone, this movie is a prime example.

71. Sleepless in Seattle

We all loved watching this relationship bloom. You can’t miss Tom Hanks in this classic.

72. Stepmom

If you know what it’s like to have a stepmom, this one will definitely pull at the heartstrings. You know, when you’re in the mood for a nice, long cry.

73. Summer Catch

Summer nights and young love. What more do you want? It’s also perfect if you’re a fan of baseball!

74. Sweet Home Alabama

No one forgets their first love. First love is the best love. Listen to the song after!

75. The Devil Wears Prada

Need a little motivation to follow your dreams? New jobs are always interesting. Anne Hathaway has you covered.

76. The Fault In Our Stars

Incredibly sad and undeniably uplifting- a must see. Another one where you’ll definitely want to have tissues handy.

77. The Holiday

Jude Law brings the hot accent, Jack Black brings the humor. Together, this is an unforgettable chick flick. You can easily find it on around the, you guessed it, the holidays.

78. The Jane Austen Book Club

Six stories of relationship and love. Get ready for a rollercoaster!

79. The Longest Ride

Young love meets old love. Strap into your seat for this ride. You even  get to see Clint Eastwood’s son!

80. The Lucky One

War, love and drama. Zac Efron takes a stab at chick flicks and does okay. See Taylor Schilling before she was in Orange Is The New Black!

81. The Notebook

I shouldn’t have to give an explanation for this one, but really, if you’ve never seen this one get ready for the chick flick benchmark. Ryan Gosling doesn’t dissapoint.

82. The Parent Trap

The newer version or the older version; both will leave you smiling with nostalgia. Who can forget Lindsay Lohan?

83. The Princess Bride

In my opinion, one of the greatest love stories of all time!

84. The Princess Diaries

The ultimate ugly duckling. Who wouldn’t want to be a real princess? Anne Hathaway is the best. Definitely a classic throwback as well.

85. The Proposal

Witty and adorable. One of Ryan Reynold’s earlier chick flicks! I’ll watch anything with him in it.

86. The Sweetest Thing

One wo watch with your besties. If you like Cameron Diaz, add this to your list.

87. The Time Traveler’s Wife

You thought your relationship was complicated? Try staying in one when you’re always traveling through time! Rachel McAdams, Eric Bana and lots of drama- love it. 

88. The Vow

Rachel McAdams does it again. Definitely up there with The Notebook for me.

89. The Wedding Date

If Dermot Mulroney didn’t prove he was made for chick flicks in My Best Friend’s Wedding, he does in this movie.

90. The Wedding Planner

Wedding planning is always stressful, but it makes for great movie. J. Lo and Mathew McConaughey make for one attractive pair.

91. Titanic

The most iconic of them all. How could this not be on your list? Kate and Leo will always be goals.

92. Twilight

The one that started it all. Team Edward or Team Jacob? And sexy vampires, that is all.

93. Valentine’s Day

Judging by the name, how could this not be a chick flick. Whether you love or hate the holiday, you need to see this one!

94. What A Girl Wants

When Amanda Bynes made movies, I must say, they were good!

95. What Women Want

The one time Mel Gibson made our hearts melt.

96. When Harry Met Sally

Another classic to add to the books. We’re all looking for our Harry and Sally.

97. Where the Heart Is

A movie about friendship and sisterhood; we’d say this is a great one to watch with mom!

98. While You Were Sleeping

Not only did we fall in love with this movie, this was the first time we fell in love with Sandra Bullock- such a cutie!

99. Win a Date With Tad Hamilton

What’s better than love triangles? They’re confusing, exciting, but make for a great chick flick!

100. You’ve Got Mail

Internet dating. The movie that started it all.

Have any other chick flicks to add to the list? Share in the comments!

Featured image source: stylemebright.com
Ashley Rego

Ashley is the Editorial Director of SOCIETY19. She is a graduate of Marist College with a degree in Business and Marketing.

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