The top 40 chick flicks of all time

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Top 40 Chick Flicks

From classic romantic comedies to films that celebrate female friendship and empowerment, Hannah Lewis picks 40 of the best chick flicks of all time

1. Four Weddings and a Funeral, 1994

There was a time when it felt like a chick flick wasn’t really a chick flick if Hugh Grant wasn’t in it. This Richard Curtis film stars Hugh at this floppy-haired best and will have you laughing and crying in equal measure. As an aside: the 90s may be back in fashion, but this film will remind you just how badly dressed we really were.

2. Mean Girls, 2004

This film turns the American teen drama genre on its head thanks to Tina Fey’s impeccable comedy writing. Clever, warm, and above all hilarious, Mean Girls became a cult classic almost immediately. There’s even a Mean Girls day (October 3rd), though you’ll have to watch to find out why.

3. The Wedding Planner, 2001

A wedding planner (Jennifer Lopez) falls for a charming paediatrician (Matthew McConaughey) only to find out he’s engaged…and she’s planning his wedding. The combination of McConaughey’s Southern charm and J-Lo at her girl-next-door best can’t fail to put a smile on your face.

4. Bridesmaids, 2011

When down on her luck Annie is asked to be maid-of-honour for her oldest friend, Lillian, she doesn’t expect to be undermined and challenged at every turn by Lillian’s beautiful and very rich new BFF, Helen. Kristen Wiig, Melissa McCarthy, Maya Rudolph and Rose Byrne deliver outstanding comic performance in this grown-up girls’ film, which somehow balances a deep and honest emotional story with silly, physical – and even toilet – humour.

5. Coyote Ugly, 2000

When small town girl Violet leaves her home in search of musical success in New York, it’s all going a bit wrong until she stumbles across a group of girls that work at a very cool bar called Coyote Ugly. Working at the bar helps her get over her stage fright, and meet a lovely man, but will she ever get to be a famous songwriter?

6. While You Were Sleeping, 1995

Every day Lucy watches the handsome Peter on his commute. When she saves his life, a classic rom-com style mix-up leads his family to believe she’s engaged to the now comatose Peter. As she falls in love with his family – and his brother in particular – how can she tell them her secret?

7. Bridget Jones’ Diary, 2001

30-something Bridget Jones is single, always on a diet, and always doing and saying the wrong thing. She starts dating her handsome boss and thinks things are looking up, but is he everything she thinks he is? And should she really have dismissed boring Mark Darcy so quickly? Renée Zellweger was received an Oscar nomination for her portrayal of Bridget Jones, a rare achievement for a ‘chick flick.’

8. Pride and Prejudice, 2005

When you’ve finished Bridget Jones’ Diary, it’s time to discover the original version of her story: Pride and Prejudice. Jane Austen may have been writing 200 years ago but her love stories are as relevant today as they were then. Keira Knightley absolutely stuns as Lizzie Bennett in this film adaptation.

9. Step Up, 2006

They may have split in real life, but Jenna Dewan and Channing Tatum have an undeniable chemistry in the first film in the successful Step Up franchise. She’s a well-to-do dance major at a prestigious art school, he’s a break dancer from the wrong side of the tracks. When they start dancing together, magic happens.

10. Legally Blonde, 2001

Reese Witherspoon is simply perfect as Elle, a Barbie-esque sorority girl who gets dumped by her boyfriend and then follows him to Harvard Law School to try and win him back, becoming a star student along the way. Between Elle’s one-liners, its theme of female empowerment, and a hilarious supporting role from Jennifer Coolidge, this is one of the most feel-good chick flicks ever made.

11. The Sweetest Thing, 2002

The Sweetest Thing follows three 20-something best friends as they navigate single life and dating. While the central love story is entertaining enough, it’s the tongue-in-cheek tone and deliciously dirty snippets that really make this film a winner. It’s as much about how the three women love and support each other as it is about the romantic relationships they embark on.

12. The Notebook, 2004

The Notebook is a beautiful tale of enduring love that will have you reaching for the tissues time and again. Rachel McAdams and Ryan Gosling deliver wonderful performances and you’re sure to fall in love with them both. Unbelievably, Gosling was cast in the role because he looked ‘ordinary’.

13. Bring it On, 2000

Bring it On follows head cheerleader Torrance (Kirsten Dunst) as she battles to ensure her cheerleading squad wins at Nationals. Torrance and the all-white Toros cross paths with the Clovers, an African American squad from a rival school whose original cheers look like they could steal the trophy. It’s fun and high energy and addresses some serious issues without taking itself too seriously.

14. Notting Hill, 1999

Another Richard Curtis classic, Notting Hill unites two of the greatest rom-com actors of all time: Julia Roberts and Hugh Grant. Will (Grant) is a simple bookstore owner who falls in love with Anna (Roberts), a Hollywood star. But can he deal with dating the most famous woman in the world?

15. Miss Congeniality, 2000

Sandra Bullock plays Gracie Hart, an FBI special agent whose glittering career hides a hopeless personal life. When a murder plot is discovered at the Miss United States beauty pageant, Gracie must go undercover as a contestant to find the bomber. Cue an impressive makeover and all manner of laughs.

16. 10 things I Hate About You, 1999

This cult classic speaks to the moody teenager in all of us. Julia Stiles plays Kat, an antisocial high school senior whose younger sister, Bianca, is the most popular girl in school. For Bianca to be allowed to date, Kat must do so first, so Bianca’s love interest Cameron pays bad boy Patrick (Heath Ledger) to try and melt the ice queen. Kat is the headstrong individual we all wish we were, and Patrick is the rebel with a heart of gold we all wanted to date.

 17. Never Been Kissed, 1999

Dowdy 20-somethig journalist Josie (Drew Barrymore), who was wildly unpopular in her teens, goes undercover at a high school to work on a story. With the help of her brother, she finally breaks into the cool crowd, but is it everything she hoped it would be? Along the way she falls in love with her English teacher, but if she wants to keep her job she can’t tell him she’s actually his age…

18. Save the Last Dance, 2001

Promising classical dancer Sara (Julia Stiles) has her world turned upside down when she loses her mother and moves in with her estranged father. Her new neighbourhood and school are predominantly African American, and the film explores race relations as well as young love through her relationship with Derek (Sean Patrick Thomas). Along the way, Derek helps Sara develop her dance by introducing her to hip-hop.

19. The Fighting Temptations, 2003

The inimitable Beyoncé stars alongside Cuba Gooding Jr in this musical comedy drama. A scam artist returns to his home town to run the church choir in the hope of securing an inheritance and perhaps a choir competition cash prize too. But back in his childhood home, surrounded by honest, hardworking people, he begins to question his choices. Oh, and he falls in love with Lilly (Beyoncé) as soon as he sees her. Who wouldn’t?

20. Down with Love, 2003

Down with Love is a pastiche of 1960s American romantic comedies, a fact which is reflected in every aspect of the film, from the dialogue to the sets and costumes. It’s visually a delight, and it’s also a fun and quirky consideration of the power struggle between men and women.

21. Pretty Woman, 1990

If you haven’t seen Pretty Woman yet, where have you been? The iconic romantic comedy charts the unlikely love story between Julia Roberts’ character Vivian, a call girl, and Richard Gere’s Edward, a high-powered businessman. It’s a modern-day fairy story that has aged fantastically, and the chemistry between the two leads is legendary.

22. The House Bunny, 2008

When sweet but simple Shelley gets kicked out of the Playboy Mansion for being too old (she’s 27!), she stumbles across a down on its luck sorority and signs up to be house mother for its nerdy sisters. Anna Faris is perfect as the hopeless Shelley, and Emma Stone is hilarious as the clever yet clueless Natalie. It’s an underrated chick flick.

23. Muriel’s Wedding, 1994

Toni Colette plays Muriel in this cult Australian comedy drama, a young girl who’s obsessed with two things: ABBA and getting married. When she runs into an old school friend, the charismatic and carefree Rhonda (Rachel Griffiths), she realises she’s been looking for happiness in all the wrong places.

24. I’m with Lucy, 2002

The often overlooked I’m with Lucy offers something of a guessing game to viewers. The title character goes on five dates with five different men, but we see them spliced together out of sequence. You’re left on the edge of your seat wondering who she ends up with. Will it be the cute but scatty Barry, the tall, dark and handsome Luke, or the witty and lovable Doug?

25. 27 Dresses, 2008

Super-organised Jane (Katherine Heigl) is always helping her friends with their weddings. So much so that she’s been a bridesmaid 27 times. She’s also nursing a hopeless crush on her boss and trying to deal with a beautiful but selfish sister. Luckily the devilishly handsome Kevin (James Marsden) turns up to help her see things differently.

26. Dirty Dancing, 1987

The line ‘Nobody puts Baby in the corner’ is perhaps one of the most famous film quotes of all time, and if you haven’t yet watched Dirty Dancing you simply must see what all the fuss is about. An indie film that made it big, it won over audiences across the world with its moving love story, amazing soundtrack and sultry dance scenes.

27. Love Actually, 2003

Love Actually practically invented the ensemble cast rom-com. Following a variety of interwoven love stories, played out by an all-star cast including many of Britain’s finest actors, the film explores the many forms that love can take, from first love and new romances to friendship and marriage.

28. Clueless, 1995

A modern interpretation of Jane Austen’s novel Emma, Clueless follows the wealthy and beautiful Cher as she navigates high school, friendships, love and growing up. Even after more than 20 years this is still one of the funniest and most relevant coming-of-age films out there.

29. Thelma and Louise, 1991

One of the most famous films ever about female friendship, Thelma and Louise follows two women as they embark on a road trip and fall into trouble they simply couldn’t have seen coming. This is one to watch with your girl friends.

30. Romy & Michelle’s High School Reunion, 1997

Two kooky best friends get invited to their high school reunion but worry their real jobs won’t impress, so they plan to fool their former peers into thinking they’re successful businesswomen. Lisa Kudrow and Mira Sorvino are fantastic as the quirky and loveable title characters and the costume design is out of this world good.

31. How to Lose a Guy in 10 Days, 2003

Kate Hudson and Matthew McConaughey star in this classic romantic comedy. Journalist Andie (Hudson) is commissioned to write an article titled, you guessed it, How to Lose a Guy in 10 Days. Ben (McConaughey) has wagered that he can make a woman fall in love with him in the same amount of time. She’s doing everything she can to annoy him, he’s desperately trying to make it work…I wonder if they’ll fall in love?

32. She’s All That, 1999

A 1990s reimagining of My Fair Lady (which itself is an interpretation of the play Pygmalion), She’s All That sees a high school jock bet that he can turn an artsy unpopular girl into a prom queen in just six weeks. Predictably, it turns out that contact lenses and a haircut were all it needed to turn ‘nerdy’ Laney into a beauty. But predictability is often half the charm of chick flicks, and this is a sweet film that will melt your heart.

33. 13 Going on 30, 2004

Jennifer Garner is simply adorable as Jenna, who makes a wish on her 13th birthday to skip to age 30 and wakes up the next day having done just that. It’s hardly a revolutionary storyline but Garner is wonderful, and Mark Ruffalo is perfect as her slightly grumpy boy-next-door love interest.

34. Pitch Perfect, 2012

Who would have known that such hilarity could ensue from a film about university a capella groups? With an incredibly talented cast, a script bursting with witty one-liners and – of course – a killer soundtrack, Pitch Perfect has become a phenomenon. And with good reason.

35. When Harry Met Sally, 1989

When Harry Met Sally is one of the most famous romantic films ever made. Following the two title characters as they meet on and off over 12 years, it poses the question, can men and women ever just be friends? Their will-they-won’t-they relationship is just one element of this classic film that has gone on to inspire countless films that came after.

36. My Best Friend’s Wedding, 1997

Julianne and her best friend Michael have had a pact since college: if they’re both still single at 28, they’ll get married. When Julianne gets a call from Michael just before the deadline to say he’s engaged to another woman, she realises she’s in love with him and rushes to try and break up the happy couple. This critically acclaimed film is considered one of the best romantic comedies of all time.

37. Crazy Stupid Love, 2011

Recently divorced Cal (Steve Carell) gets schooled in the art of picking up women by serial womaniser Jacob (Ryan Gosling). All the while Jacob’s playboy ways are being challenged as he falls in love with the bright and charming Hannah (Emma stone). A clever and witty film that shows Stone and Gosling at their best.

38. Trainwreck, 2015

Commitment-phobic party girl Amy (Amy Schumer) struggles to change her ways after meeting Aaron, a funny and genuinely nice guy who wants to be in a relationship. This is a chick flick for anyone who says they don’t like chick flicks: clever, honest and laugh-out-loud funny.

 39. The Holiday, 2006

Two women – one living in LA and one in Surrey – decide to take a break from their nightmare love lives by swapping houses for the Christmas holidays. They both find themselves falling for men in their new locations, but is it long-term or just for the holiday?

40. Girls Trip, 2017

If you liked Bridesmaids, you’ll love Girls Trip, which follows four best friends who have drifted apart in the years since college but reunite for a girl’s weekend in New Orleans. It’s hilarious, it’s risqué, and it’s just great to see a film about successful women supporting successful women.


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