30 Comedies Every Woman Needs To See Before Turning 30

Photo: Moviestore/REX/Shutterstock.
First of all, if you’re here to find a list of movies like Airplane, This Is Spinal Tap, Caddyshack, Office Space, or Ghostbusters, you’ve come to the wrong place. This ain’t that list. If you’re looking for a generic roundup of the generally agreed-upon films you should have in your comedy canon, might we direct you to this one from The Guardian, or this one from Time Out.

What you’re about to read is a carefully curated list of films that celebrate the more humorous parts of the female experience — for smart women who appreciate watching it in said way. If your favorite part of perusing Seventeen was always reading the Traumaraumas out loud with your friends, we feel you. This list is 100% your jam. Also, who among us hasn't flown too close to the sun by testing the absorbency limits of a tampon? It's all part of the learning curve, friends.

These movies celebrate all the joy, pain, and douleur exquise of the female experience in a way that’ll make you laugh, cry, and craugh (a new world we’re coining for laughing while crying). Because that’s what’s involved in being a woman sometimes: finding humor in even the most difficult of situations.

Some of the films are pure silliness. Others are extremely dark and subversive. This is the essential comedy canon, though, to make you silently sing, “I Enjoy Being a Girl” — and know that you're never alone on this, your female mortal coil.

P.S. In some cases, we’ve suggested an additional film with which to pair a given movie. Because, much like pretzels and frosting, some things just go better together, you know?
Advertisement
1 of 30
Bringing Up Baby (1938)
Starring: Katharine Hepburn, Cary Grant

A delightful screwball comedy about a tame leopard named Baby who’s mistaken for a dangerous circus leopard; a paleontologist (Grant) who’s mistaken for a zoologist and therefore asked for help bringing up Baby; and a woman named Susan (Hepburn) who’s at the center of all the cases of mistaken identity.

Watch it: Amazon, iTunes, Google Play
2 of 30
The Women (1939)
Starring: Norma Shearer, Joan Crawford, Rosalind Russell

You won’t see a single male in this film following the interconnected lives of various Manhattan women. Not a one!

Watch it: Amazon, iTunes, Google Play
Advertisement
3 of 30
The Philadelphia Story (1940)
Starring: Cary Grant, Katharine Hepburn, James Stewart

A divorced socialite (Hepburn) is set to remarry, but her ex-husband (Grant) and a tabloid reporter (Stewart) show up to throw a wrench in her plans.

Watch it: Amazon, iTunes, Google Play
4 of 30
Roman Holiday (1953)
Starring: Audrey Hepburn, Gregory Peck

A sheltered European princess (Hepburn) wanders off in Rome and is discovered by an American reporter (Peck). She decides it’s time to live a little fun. He decides it’s time to make some money. Falling in love ensues, obviously.

Watch it: Amazon, iTunes, Google Play, Netflix
5 of 30
Some Like It Hot (1959)
Starring: Marilyn Monroe, Tony Curtis, Jack Lemmon

Two jazz musicians (Curtis and Lemmon) on the run from the mob in Chicago disguise themselves as women and join an all-female band en route to Miami. They both fall for the band’s singer/ukulele player (Monroe), but their entanglement with the Mafia isn’t over yet.

Watch it: Amazon, iTunes, Google Play
6 of 30
Annie Hall (1977)
Starring: Diane Keaton, Woody Allen

Neurotic comedian Alvy Singer (Allen) falls in love with cool, menswear-sporting icon Annie Hall (Keaton). When their relationship unravels, Alvy desperately tries to figure out what went wrong.

Watch it: Amazon, iTunes, Google Play
7 of 30
Private Benjamin (1980)
Starring: Goldie Hawn, Eileen Brennan, Armand Assante

Judy Benjamin is a spoiled, sheltered 28-year-old who’s never experienced any hardship until her new husband (Albert Brooks) dies during sex on their wedding night. An Army recruitment officer (Harry Dean Stanton) convinces Judy that the military can provide the kind of sheltered family experience she’s used to. Obviously, Private Benjamin is in for a very rude awakening.

Pair Private Benjamin with the charming Troop Beverly Hills, in which an equally spoiled and sheltered woman (Shelley Long) decides to lead a troop of Wilderness Girls in Beverly Hills.

Watch Private Benjamin: Amazon, iTunes, Google Play
Watch Troop Beverly Hills: Amazon, iTunes, Google Play
Advertisement
8 of 30
Tootsie (1982)
Starring: Dustin Hoffman, Jessica Lange

An actor (Hoffman) can’t get hired because he has a reputation for being difficult, so he pretends to be a woman. His female alter ego soon becomes a soap opera star.

Watch it: Amazon, iTunes, Google Play
9 of 30
The Princess Bride (1987)
Starring: Robin Wright, Cary Elwes, Mandy Patinkin

When the evil King Humperdinck (Chris Sarandon) decides to marry Buttercup (Wright), the love of Westley’s (Elwes) life, Westley sets off on a quest to get her back.

Watch it: Amazon, iTunes, Google Play
10 of 30
Moonstruck (1987)
Starring: Cher, Nicolas Cage

A widow (Cher) accepts a marriage proposal from her boyfriend (Danny Aiello), only to wind up falling for his younger brother (Cage).

Watch it: Amazon, iTunes, Google Play
11 of 30
Working Girl (1988)
Starring: Melanie Griffith, Harrison Ford, Sigourney Weaver

An extremely driven woman (Griffith) from Staten Island discovers that her boss (Weaver) is taking credit for her big idea, and she sets out to fix the situation. If you’re looking for another “ladies sticking it to the man and overcoming institutionalized sexism in the workplace” comedy (starring Dolly Parton!), cue up 9 to 5.

Watch Working Girl: Amazon, iTunes, Google Play
Watch 9 to 5: Amazon, iTunes, Google Play, Netflix
12 of 30
Heathers (1988)
Starring: Winona Ryder, Christian Slater

Veronica Sawyer (Ryder) hates the Heathers — the vicious, bitchy girls she pretends are her friends, who all happen to be named Heather. When sexy loner J.D. (Slater) moves into town, he goads Veronica into acting on her fantasies of murdering the popular people at their school together.

Watch it: Amazon, iTunes, Google Play, Netflix
Advertisement
13 of 30
Sister Act (1992)
Starring: Whoopi Goldberg, Maggie Smith, Kathy Najimy

A Vegas lounge singer (Goldberg) hides out from the mob in a convent after she walks in on her gangster boyfriend (Harvey Keitel) having someone executed, and he orders a hit on her as well.

Watch it: Amazon, iTunes, Google Play
14 of 30
Welcome to the Dollhouse (1995)
Starring: Heather Matarazzo, Daria Kalinina

Middle schooler Dawn Weiner struggles with bullies, her parents’ lack of interest in her (and over interest in her siblings), and the other joys of adolescence.

Watch it: Amazon, iTunes, Google Play
15 of 30
Clueless (1995)
Starring: Alicia Silverstone, Paul Rudd, Stacey Dash

Impossibly stylish Beverly Hills high schooler Cher Horowitz (Silverstone) lovingly meddles in her friends’ and teachers’ lives.

Watch it: Amazon, iTunes, Google Play, Netflix
16 of 30
Walking and Talking (1996)
Starring: Catherine Keener, Anne Heche

Two women who have been friends since childhood reach a crossroads in their lives when one of them (Heche) gets engaged, while the other (Keener) is still struggling to find her identity independently of the men she dates.

Watch it: Amazon, iTunes, Google Play, Netflix
17 of 30
The First Wives Club (1996)
Starring: Bette Midler, Goldie Hawn, Diane Keaton

Three divorced women (Midler, Hawn, and Keaton) decide to get revenge on their ex-husbands, who all left them for younger women.

Watch it: Amazon, iTunes, Google Play
Advertisement
18 of 30
Romy & Michele’s High School Reunion (1997)
Starring: Lisa Kudrow, Mira Sorvino

Two best friends (Kudrow and Sorvino) haven’t quite accomplished what they hoped since finishing high school, but when their 10-year reunion rolls around, they decide to concoct an elaborate fantasy life for themselves to impress their classmates.

Watch it: iTunes, Google Play
19 of 30
Drop Dead Gorgeous (1999)
Starring: Denise Richards, Kirsten Dunst, Ellen Barkin

A dark satire about the horrors of teen beauty pageants.

Watch it: Google Play
20 of 30
Election (1999)
Starring: Reese Witherspoon, Matthew Broderick

An even darker black comedy about a high school election that ruins a man's life thanks to one type-A student.

Watch it: Amazon, iTunes, Google Play, Netflix
21 of 30
Legally Blonde (2001)
Starring: Reese Witherspoon, Luke Wilson, Jennifer Coolidge

Further proof that you should never judge a book by its Valley Girl-esque cover. She might just turn up at Harvard Law one day.

Watch it: Amazon, iTunes, Google Play, Netflix
22 of 30
Ghost World (2001)
Starring: Thora Birch, Scarlett Johansson

High school seniors and best friends Enid (Birch) and Rebecca (Johansson) have no life plans beyond graduation besides getting an apartment together. They decide to meddle in a lonely man’s (Steve Buscemi) life, which results in a complete falling out between the two friends.

Watch it: Amazon, iTunes, Google Play
Advertisement
23 of 30
Bend It Like Beckham (2002)
Starring: Parminder Nagra, Keira Knightley, Jonathan Rhys Meyers

Jess (Nagra) dreams of playing soccer, but her traditional Indian parents want her to follow a more practical path.

Watch it: Amazon, iTunes, Google Play
24 of 30
Mean Girls (2004)
Starring: Lindsay Lohan, Rachel McAdams

An uncomfortably spot-on portrayal of the complex and cruel mind games high school girls play with one another to remain at the top of the metaphorical food chain.

Watch it: Amazon, iTunes, Google Play
25 of 30
Saved! (2004)
Starring: Jena Malone, Macaulay Culkin, Mandy Moore

Students at a Christian school struggle with their commitment to their faith and each other.

Watch it: Amazon, iTunes, Google Play
26 of 30
Juno (2007)
Starring: Ellen Page, Jennifer Garner, Michael Cera

After a high school student (Page) gets pregnant, she decides to give the baby up for adoption and searches for the right parents in the local Pennysaver.

Watch it: Amazon, iTunes, Google Play
27 of 30
Bridesmaids (2011)
Starring: Kristen Wiig, Maya Rudolph, Rose Byrne

Annie (Wiig) wants to make her best friend Lillian’s (Rudolph) wedding the best day ever, but it’s kind of hard to be a stellar maid of honor when Annie’s own life is in a bit of a shambles. Enter Helen (Byrne), Lillian’s new BFF from the country club set she’s about to join. Helen is one of those women who’s so perfect, you actually wonder if she ever takes a shit.

For a darker take on the whole wedding industrial complex, pair a viewing of Bridesmaids with Leslye Headland’s Bachelorette (2012).

Watch Bridesmaids: Amazon, iTunes, Google Play
Watch Bachelorette: Amazon, iTunes, Google Play
Advertisement
28 of 30
Moonrise Kingdom (2012)
Starring: Kara Hayward, Jared Gilman

Two madly in love 12-year-olds (Hayward and Gilman) flee their respective homes and run away together, throwing the people they left behind into a state of chaos. Pair this with any other Wes Anderson creation, really, but you’ll probably identify with Margot Tenenbaum (Gwyneth Paltrow) in The Royal Tenenbaums the most.

Watch Moonrise Kingdom: Amazon, iTunes, Google Play, Netflix
Watch The Royal Tenenbaums: Amazon, iTunes, Google Play
29 of 30
Pitch Perfect (2012)
Starring: Anna Kendrick, Skylar Astin, Rebel Wilson

It’s a cutthroat world out there on the college a cappella scene, and Beca (Kendrick) wants no part of it/hasn't even heard of it when she arrives at Barden University. Well cue up the “Since U Been Gone” audition montage, because someone’s about to get pitch-slapped.

Watch it: Amazon, iTunes, Google Play
30 of 30
Spy (2015)
Starring: Melissa McCarthy, Rose Byrne, Jason Statham

The CIA’s best field agent (McCarthy) is actually someone they’ve stupidly confined to a desk job for years in this hilarious sendup of every spy movie ever.

Watch it: Amazon, iTunes, Google Play
Advertisement

More from Movies

Watch

R29 Original Series