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Greatest Chick Flicks Ever

Updated on June 23, 2018

So what does it mean for a movie to be termed a Chick Flick? I think that term means a lot of different things to different people. I have heard some describe a chick flick as a film in which the prominent characters are women and involves intense female bonding. I have also heard chick flick movies described as dramas with strong emotional elements usually concluding with most of the audience in tears. Still others describe chick flicks as romantic movies whether dramas or comedies. Finally, I have heard chick flicks described as movies with strong female leads as role models that other women wish to emulate.

I tend to fall in the final camp and feel a good chick flick is about empowerment, in which a female lead exhibits strong character traits and overcome large odds to succeed in her goal. But whatever your own definition, I think you will find that these top chick flicks leave a lasting impression long after you watch them.

They list includes movies that are both old and new. Some were Oscar nominated gems and others were just classic films that women the world over can relate to. Most of these top chick flicks involve a really good love story and sometime it is unrequited love. Others are great films about family relations and building bridges across wide chasms built up over years of relationship damage. These themes are common in the best chick flicks and you will find them prominently utilized in our list.

If you are a big fan of chick flicks, then I have some other suggested sites to visit. Your first stop for info on the best romantic comedies should be JustChickFlicks created by Clarabela. She really does a great job with the romantic movies genre.

We have also created top ten lists for two of the biggest chick flicks movies stars, you can browse these lists to find films you might have missed: Julia Roberts Movies and Anne Hathaway Films.

All rights reserved. Copyright 2011 Rankography

10. Whip It (2009)

Drew Barrymore's Directorial Debut

In Drew Barrymore's Whip It, 17 year old Bliss Cavendar (Ellen Page) is a small town girl who is struggling to stretch her wings in the small Bodean, Texas. Her mother, Brooke Cavendar (Marcia Gay Harden), believes Bliss has what it takes to win beauty pageants. Bliss, on the other hand, is quiet and shy and does not like pageants. When she finds a roller derby team in nearby Austin, she decides to tryout. Turns out Bliss is very fast and a star on the team. She has not told her mother about the roller derby and there will be hell to pay when she finds out.

Drew Barrymore both directed and starred in this film as one of Bliss's roller derby teammates. This was Barrymore's first directorial effort and the film is quite good. The cast also includes Jimmy Fallon, Kristen Wiig and Daniel Stern. The plot and storyline are a bit simple but for a simple enjoyable romp, this chick flick is quite entertaining.

If you liked Whip It, you might also want to check out Bring it On featuring Kristen Dunst which is about two rival cheerleading squads competing for the National Championships.

9. Legally Blonde (2001)

One of the Best Chick Flicks of the 2000s

Legally Blonde is a fun comedic empowerment chick flick. Elle Woods (Reese Witherspoon) skates through high school and college as the ultimate girly girl. She has simple needs (fashion, fun and boys) and one simple goal; to marry her beau-hunk boyfriend, Warner (Matthew Davis), and settle down to have children.

Of course, life is never quite that simple. Warner has other ideas of the "perfect wife" and dumps Elle on the eve of graduation. After enduring the initial devastation, Elle decides to apply to Harvard Law School to follow Warner. The absolute absurdity of so much of this movie keeps us laughing along the way.

Adapted from a brilliant Broadway stage play of the same name, Legally Blonde and Reese Witherspoon are deliciously funny. You root for Elle to overcome her obstacles throughout the film. Despite much of its tongue in cheek humor, this chick has a strong empowerment message for young girls; you can do anything you set your mind to.

If you liked Legally Blonde, you might also want to check out Crazy Stupid Love with its star studded cast in which Ryan Gosling plays a ladies man trying to mold a middle-aged Steve Carrell into one himself.

8. The Way we Were (1973)

Streisand and Redford Create a Classic for the Ages

The Way we Were is one of the all time great love story films and like most romance movies it ends in tears. The story revolves around Katie (Barbara Streisand) and Hubbell (Robert Redford) who originally met and became friends during college. However, they are from very different worlds. Katie is an erudite New Yorker while Hubbell was a handsome jock with a simpler sensibility. The reunite about 10 years after college and Hubbell has become a writer, while Katie is a political activist and organizer. They enjoy an on again, off again affair that ultimately results in marriage.

However, their relationship is tumultuous and they realize they have a different set of ideals and widely differing political views. Barbara and Redford have outstanding chemistry together and Streisand was nominated for an Oscar for this role. The film score for this film did win an Oscar and is quite outstanding with Barbara performing much of the score.

It is a touching film that also highlights the fragile nature of love. It is one of the most romantic films while also being an extreme tearjerker chick flick.

If you liked The Way We Were, you should also check out The Notebook a more recent, yet no less enduring love story that spans decades.

7. When Harry Met Sally (1989)

Great Friends Find Love Together

One of the best romantic comedies of all time, When Harry met Sally, is also a favorite chick flick for many women. Over a 12 year period, Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) maintain a deep friendship, but they are only friends. Eventually, the two realize their their friendship is actually much more and they fall in love. The film explores the question, can a single man and a single woman actually be "just friends. At the time it was an original question, but it laid the foundation for many of the top romantic comedies that have followed and is now one of the most copied formats.

It was a superb team led by Director, Rob Reiner, Billy Crystal as the boy and Meg Ryan as the girl. Carrie Fisher and Bruno Kirby also add excellent supporting roles. This film is one of the best chick flicks and a superb romantic comedy.

If you liked When Harry met Sally, you might also want to check out Dirty Dancing which many consider to be the ultimate Chick Flick. Its the story of a high school girl on summer vacation in the Catskills who falls in love with the camp's dance instructor. True devotees have seen this film dozens of times.

6. Pretty in Pink (1986)

John Hughes and Molly Ringwald Team Up Again

Pretty in Pink is a feel good romantic comedy chick flick. Andie Walsh (Molly Ringwald) is the poor daughter of a widowed father, Jack (Harry Dean Stanton). Like in most John Hughes (Writer) films, Andie is struggling to find herself as a "non-popular" girl during the awkward teenage years.

In this top chick flick, Andie is trying to decide between which of two admirers should get her attention, her long-time geeky best friend, Ducky (Jon Cryer) or the sauve rich, but sensitive kid, Blane (Andrew McCarthy).

This simple rich boy, poor girl theme is a role reversal from the more common rich girl, poor boy theme for romantic comedies. While not as funny as Hughes, Sixteen Candles, it is a more endearing romantic film. Cryer is quite funny as Duckie and Annie Potts is excellent as Andie's other screwball friend, Iona.

If you are looking for a light-hearted romantic comedy that is also one of the great chick flicks, you can't go wrong with Pretty in Pink.

If you liked Pretty in Pink, then you also have to see Bridget Jones Diary, starring Rene Zellweger, which is the modern day retelling of Jane Austen's Pride and Prejudice.

5. Terms of Endearment (1983)

One of Nicholson's Best Films is Also a Great Chick Flick

Terms of Endearment is a wonderful film that will covers all the emotions, you will laugh, you will cry and in the end you will feed deep empathy for the characters and their lives. Aurora Greenway (Shirley MacLaine) and her daughter Emma Horton (Debra Winger) are two very different animals and they struggle to maintain a relationship over the years. However, Emma's sickness brings them closer together and they find some common ground do develop a deep emotional bond.

Meanwhile, next door neighbor Garrett Breedlove (Jack Nicholson) is a free spirit, retired astronaut, who tries to loosen up emotionally closed Aurora. This wonderful film explores the roles we assume in our lives and ways we can breakout of the molds that have developed during our long lives. It is a celebration of life despite the sadness of preparing to lose one of the key characters.

This outstanding chick flick won 5 Oscars including, Best Picture, Best Director, Best Actress (MacLaine), Best Supporting Actor (Nicholson) and Best Adapted Screenplay. If you have never seen this great chick flick, it is one of those films you must see.

If you loved Terms of Endearment, then you have to see Fried Green Tomatoes, starring Kathy Bates and Jessica Tandy. It is one of my all time favorite historical flashback films and the story and acting are brilliant throughout.

Classic Gone with the Wind Movie Poster
Classic Gone with the Wind Movie Poster

4. Gone With the Wind (1939)

A Classic Epic Film is Also One of the Great Chick Flicks

Gone with the Wind is the ultimate film in a lot of categories, including Epics, Unrequited Love Stories and possibly Chick Flicks. This epic drama follows the story of Scarlett O'Hara (Vivien Leigh), a manipulative, self-centered Southern belle during the Civil War and Reconstruction. Scarlett wants to marry a Southern gentlemen, Ashley Wilkes (Leslie Howard), who loves another woman, so she must "settle" for a dashing, but rough-cut Rhett Butler (Clark Gable).

This sweeping Epic covers the entire period of the Civil War from its beginning in 1861 through the first few years after the war's end. During this time, the O'Hara plantation, in Georgia, is over-run and looted, Atlanta burns and many of Scarlett's friend and family dies.

She is forced to lead and protect her family during this difficult time. While married to Butler, their tumultuous relationship is accented by powerful one-liners throughout this film.

This epic chick flick won 8 Oscars, including Best Picture, Best Director, Best Actress and Best Screenplay. Leigh and Gable were outstanding together and the entire supporting cast is excellent. Often considered one of the best movies of all time, it definitely rates as one of the greatest chick flicks ever.

If you loved Gone with the Wind, then you also have to check out Casablanca which is also one of the all time historical fiction tragic love stories. Unlike GWTW which is set during the Civil War, Casablanca is set during the beginning of World War II. Starring Humphry Bogart and Ingrid Bergmann, it is one of the most enduring classic films.

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For your son's room, you should check out the Fathead's from his favorite sports team, or this Disney Cars Collection or maybe he is more of a Star Wars fan.


3. Breakfast at Tiffany's (1961)

The Quintessential Chick Flick

In Audrey Hepburn's most memorable role as Holly Golightly, she is brilliantly funny and wacky. A quirky New Yorker with a penchant to party in a sophisticated NY manner. When Paul Varjak (George Peppard) moves into her building, he immediately falls for this whimsical gal. Of course, Holly has her own goal to marry the Jose (Jose Luis de Vilallonga), a South American millionaire.

Directed by Blake Edwards, he created just the right mix of romance, style and wit. Hepburn is absolutely fabulous and incredibly charming in this chick flick. Her sense of style and sophistication reminded me of a female Cary Grant.

If you have never seen this chick flick, you must move it right to move it to the top of you must see list. You will not be disappointed.

If you liked Breakfast at Tiffany's, you might also want to check out Roman Holiday starring Gregory Peck and Audrey Hepburn. This was the film that first brought Audrey to prominence and the World went weak at the knees as a result. Hepburn grabbed the Oscar for her portrayal of a princess in this film.

2. The Devil Wears Prada (2006)

Streep is Excellent as the Ice Queen, Miranda Priestly

Andrea Sachs (Anne Hathaway) has just graduated with a Journalism degree and is looking to put that to work with a magazine in New York. She is an intellectual with strong political views but on a whim she ends up in an interview for a top fashion magazine. Miranda Priestly (Meryl Streep) is the ruthless, high-powered Editor of said fashion magazine. Somehow Andrea, with little knowledge or interest in fashion, lands the job and then the fun begins.

Streep is brilliant as the acidic, hard as nails Priestly. Her demanding, self-centered character leaves little room for mistakes, and of course Andrea starts out making quite a few. The entire office is stunned at her lack of interest in fashion, but her endearing personality makes friends throughout the industry.

As the film develops, Andrea begins to excel in her role as Priestly's assistant. The real subplot of the film is how each character begins to change a bit coming to a more central ground between the two.

This is a very funny and entertaining film and one of the best chick flicks of the 2000s. The cast is brilliant including Streep (nominated for an Oscar), Hathaway, Stanley Tucci and Emily Blunt. This is one of my favorite chick flicks and a great comedy film.

If you liked The Devil Wears Prada, you might also want to check out Julie and Julia starring Meryl Streep and Amy Adams. A frustrated office worker becomes inspired by the cookbook of legendary chef, Julia Child, and tries to recreate her life as a result.

1. Thelma & Louise (1991)

One of the Great Action Chick Flicks

Thelma & Louise is the ultimate empowerment chick flick that is part crime thriller and part dark comedy. Thelma (Geena Davis) is in a dead end relationship with a domineering male, Daryl (Christopher McDonald) who decides when and if she can do anything. Louise (Susan Sarandon) has a dead end job as a diner waitress. Together they decide to take off for a long weekend at a friend's cabin.

However, along the way they stop in a roadhouse for a couple of beers where Thelma flirts with a stranger, Harlan (Timothy Carhart). After Harlan convinces Thelma to take a walk outside the bar, Harlan comes on strong and eventually tries to rape Thelma. However, Louise interrupts the rape in progress. She has a gun and after an argument with Harlan, Louise ends up shooting and killing him.

Most of this chick flick follows Thelma and Louise as they run from the law. Along the way, Thelma is converted from a meek girl into an empowered woman willing to do what it takes to keep them from being caught. The pair is headed for the potential safety of Mexico, while police investigator, Hal (Harvey Keitel) uses all his means to prevent their escape.

This is an action-packed chick flick with a black comedy flair. There are cameos in this film by Brad Pitt and Michael Madsen. This is one of the best films for both Susan Sarandon and Geena Davis. As usual, Harvey Keitel is also excellent in this thriller. This is one of my favorite Ridley Scott films (Director) and one of the best chick flicks of all time.

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I would love to know what you think about this lens on the Greatest Chick Flicks. If you liked it, you might want to check out our other lens about the Best Movies in a number of genres.


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