The 20 Best Chick Flicks Of All Time (as of 2019)

Chick flicks have been around for decades.  A good chick flick is filled with strong emotion and involves some comedy and usually romance.  It appeals to a woman’s feelings more so than a man’s.  Action movies and full-out comedies will never fall into the chick flick category.  But start talking romantic comedy, and you have a chick flick in the making.  Here are 20 best chick flicks to brighten up a cold, rainy day:


This 1942 film starring Humphrey Bogart and Ingrid Bergman is a timeless classic.  Bogart must make a choice between love and helping a Czech Resistance leader, the husband of his true love, get out of the country.

Gone with the Wind

A turbulent relationship set in the turmoil of the Civil War starring Clarke Gable and Vivian Leigh. A true classic from 1939.

Breakfast at Tiffany’s

Audrey Hepburn delivers a star performance in this 1961 romantic comedy of the life of a café society girl.  It is a classic that has spanned generations and is considered by some as an important statement about the time in history.

Dirty Dancing

This 1987 chick flick starred Patrick Swayze, who had the girls of the time instantly swooning.  It played to the age old adage of Prince Charming sweeping a seemingly normal, bland girl off of her feet.

The English Patient

Set near the end of World War II.  A badly burned English soldier is deemed to ill to be moved.  He spends his last days with a nurse in a burned out Italian Monastery.  It is a gripping tale of his quest to remember as well as to forget, and a story that brings together two unlikely characters,

The Notebook

This story of a couple in the 40s, as told by an elderly James Garner, got mixed reviews at the box office, but is still seen by many as a movie well worth watching again and again. This 2004 romantic drama is a must own.

Pretty Woman

This is a 1990 cult classic.  Yet another version of Prince Charming and Cinderella, but this one is done so well as to attract huge audiences upon its release.  Richard Gere and Julia Roberts add depth to this time-worn classic tale. 


The story of the Titanic has been a tragic romantic story since that fateful night in April of 1912.  The story of Jack and Rose will pull at the heart strings of women of any age looking for a good, enthralling chick flick.

Miss Congeniality

Sandra Bullock’s 2000 comedy is one of her best movies.  She plays a FBI Special Agent undercover in the Miss United States pageant.  It’s a story of unsuspecting friendship and love beneath the search for The Citizen, who has threatened the pageant itself.

You’ve Got Mail

Tom Hanks and Meg Ryan star in this 1998 romantic comedy.  These Business rivals in the brick and mortar world become infatuated with one another online.  Once they meet and discover each other’s true identity, it’s unclear whether the business relationship or the budding romance will win out.

Thelma and Louise

Thelma and Louise, played by Gina Davis and Susan Sarandon, has become a household name since it came out in 1991.  Its always worth another view when life starts to get dull and confining.

Something’s Gotta Give

An older man, a younger woman, a 2003 romantic comedy with an unexpected twist.  Jack Nicholson’s character is used to having every woman he has ever wanted.  But Diane Keaton could be out of his league.

10 Things I Hate About You

This 1999 Romantic dramedy stars Heath Ledger, Julia Stiles, and Joseph-Gordon Levitt.  The new kid in school must go to great lengths to get a date with his new love, who cannot date until her older sister does.  The twist being that the older sister is the meanest girl in school, and the lengths he will go to keep chick flick watchers entertained until the end.

Romy & Michelle’s High School Reunion

High school reunions are dreaded by women of all ages.  This 1997 comedy starring Mira Sorvino and Lisa Kudrow bring out the comedic worst in high school reunions.  This movie is a perfect choice for an evening of getting together with good friends, a bottle of wine, and a great movie.

When Harry Met Sally

Billy Crystal and Meg Ryan star in this 1989 romantic comedy.  Directed by Rob Reiner, this film highlights relationships, and platonic friendships that can get more complicated.  Funny, witty, and full of emotion, this movie definitely deserves its place on the Top 20 list.


A recent-comer to the chick flick market, this 2011 comedy is a must see.  A single woman with a less-than-perfect life finds herself as the bridesmaid in her best friends’ wedding.  This is a great movie to see with the bridal party, or any group of friends.

It’s Complicated

This 2009 movie stars Meryl Streep and Alec Baldwin.  That alone should make it worth watching.  The storyline between the divorced couple brings out the complications of a romance that should never have been, or should never have ended.  More than a social media status, “It’s Complicated” is a must-see chick flick of love triangles and comedy.

Terms of Endearment

This 1983 drama quickly became the quintessential chick flick.  With stars such as Shirley MacLaine, Jeff Daniels, Debra Winger and Jack Nicholson, it is easy to see why.  Follow Emma’s life from falling in love to getting divorced, to being diagnosed with terminal cancer.  This movie is a tear-jerker that showcases the highs and lows of life.

The Way We Were

This 1973 drama is worth revisiting for those who haven’t yet seen it.  The relationship struggles and choices to be made are timeless.   Barbara Streisand and Robert Redford put on great performances of love and how opposites attract.  Grab the tissues and snuggle in for this one.


This 1988 melodrama is about friendship and its enduring qualities over a lifetime.  Barbara Hershey and Bette Midler play two friends who could never let space or time separate them. Through other relationships and all of life’s ups and downs, they never lose sight of each other.  It’s a story of friendship and a true “bestie” night in movie.

There are many other chick flicks that are great entertainment.  Choosing the “best” 20 is definitely a matter of choice.  But for those looking for some great entertainment on a night alone or with friends, these 20 should fit quite well.  Human struggles are universal and all relationships have ups and downs.  These movies showcase some of the saddest, and happiest, moments life has in store.


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