Is it just me, or are coming-of-age teen comedies some of the best movies to watch in almost any circumstance? They’re funny, have interesting (but predictable) storylines and always leave you feeling good at the end.
When it comes to teen comedies, you don’t get any better than Clueless. This 90s classic has inspired hundreds of movies and TV shows over the last few decades.
But what happens when you’ve watched the movie so much that you know all the lines? What you need is movies similar to Clueless.
In this article, I’ll show you 15 films like Clueless. Read through each one and choose what you’re going to binge next.
Never Been Kissed
Josie, an up-and-coming editor, needs to go undercover at a local high school, so she researches the lives of the students attending the school.
However, Josie finds it challenging to fit in and being back in school reminds her of some unpleasant memories from her actual time in high school.
Will Josie successfully navigate her way around high school and complete her report? Or will she find her bad memories too much to deal with?
Drew Barrymore stars in this movie; she’s known for Charlie’s Angels, ET, and 50 First Dates. She’s joined by David Arquette, Michael Vartan and John C Reilly.
Heathers is a smart black comedy set in high school that deals with the various social groups that everybody associates with schools.
Veronica is part of a snobby clique consisting of three other girls named Heather. However, Veronica longs for her normal life back as she’s fed up with being “popular” and dislikes her friends.
When Veronica becomes close to a new rebellious outsider named Jason, the pair begin to kill off the Heathers one by one.
Heathers is like Clueless as it deals with the various dynamics of high school, but with a much darker twist.
The movie stars Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk, and Kim Walker.
The Breakfast Club
This movie is as iconic as Clueless; it pretty much started the teenage coming-of-age films back in the 80s.
It follows a group of five high school students from different backgrounds with different mindsets who find themselves detained together in the school library on a Saturday morning.
As time goes by, they lose their egos and develop close relationships.
It’s a must-watch if you enjoyed Clueless. Empire Online called it the “definitive 80s teen movie”. Plus, it has a killer soundtrack to boot.
The movie stars Emilio Estevez, Judd Nelson, Molly Ringwald, Ally Sheedy, and Paul Gleason.
She’s All That
If you loved the 90s vibes from Clueless, then you’ll love what She’s All That has to offer you.
Zack’s famous girlfriend, Taylor, cheats on him and ends their relationship. He boasts to his friends that he can make any girl popular, which leads to Zack and his friends placing a bet.
The bet involves Zack turning socially awkward Laney into the prom queen at the end of the year. The problem is both Zack and Laney start developing feelings for each other.
She’s All That is an easy movie to watch with plenty of 90s references to give you a hit of nostalgia.
Starring in the movie is Freddie Prince Jr, Rachael Leigh Cook, Matthew Lillard, and the late Paul Walker.
Young adult Molly is forced to find a new job when her boss steals her money. She finds work as a nanny, looking after an 8-year-old girl named Ray.
However, Ray isn’t your typical 8-year-old; she acts more grown up than Molly does. But this could be the perfect opportunity for the pair to learn something from each other. Ray can teach Molly how to be a grown-up, while Molly can teach Ray it’s OK to act like a child.
The movie shares similar cast members to Clueless.
Brittany Murphy stars in the movie; she’s known for Just Married, 8 Mile, and Girl Interrupted. Dakota Fanning and Donald Faison join her.
Before they graduate, two high school friends, Amy and Molly, realise they’ve become outsiders, and their friends have cast them aside for becoming bookworms.
In a bid to make up for lost time, they both decide to let their hair down and shake off the cobwebs while they still can.
The show is set in high school and covers some of the same social norms that Clueless does.
The movie stars Beanie Feldstein, Kaitlyn Dever, Molly Gordon, and Diana Silvers.
The Crush is a slightly more serious movie that is more psychological thriller than a teen coming of age. However, it shares similar cast members to Clueless and is a “coming of age” film of sorts.
It follows 28-year-old writer Nick who moves to a new city for work. He stays at a guest house, and the owner’s 14-year-old daughter, Adrian, makes it clear that she’s attracted to him.
He avoids the situation and starts dating a photographer, but Adrian hates that he’s not interested in her and becomes obsessed with him. Her obsession leads her to destroy his property and attack his friends.
Will he manage to get rid of his unwanted admirer before she does something worse?
The Crush stars Alicia Silverstone, Cary Elwes, Jennifer Rubin, and James G Robinson.
Legally Blonde 2
You might have heard about Legally Blonde, but Legally Blonde 2 doesn’t get the credit it deserves.
Sure, it might not be the same as the first (sequels rarely are), but it’s still a fun movie to watch and will give you the same feeling Clueless does.
In this sequel, Elle halts her wedding preparation and sets off to Washington to support a representative of an animal rights bill.
Will she manage to help the bill pass? You’ll have to watch it to find out.
The movie stars Reese Witherspoon, best known for This Means War, Sweet Home Alabama, Just Like Heaven, Walk The Line, Wild, and Election.
This movie is based on the Jane Austen novel of the same name.
Set in 1815, a wealthy young woman named Emma Woodhouse loves to play matchmaker and is constantly meddling with the romantic lives of her friends.
However, a few misguided matches and some romantic missteps lead her to find the love she didn’t see the first time.
This movie is like Regency-era Clueless; if you enjoy period dramas and films, then you’ll love what Emma has to offer.
The movie is headed by Anya Taylor-Joy, who’s known for The Queen’s Gambit, Last Night In Soho, The Northman, and The Witch.
When teenager Ren and his family move from a big city to a small town, he’s shocked to discover that rock music and dancing are illegal in his new hometown.
It’s a massive blow for Ren, a teen who loves to express himself through music, and it’s only a matter of time before his rebellious spirit shakes up the small town.
This movie is full of iconic moments and is a pure feel-good movie. It’s like Clueless as it follows a group of teenagers and doesn’t take itself too seriously.
It stars Kevin Bacon, Lori Singer, John Lithgow, Sarah Jessica Parker, and Dianne Wiest.
She’s The Man
Viola is a football-loving teen whose team is dissolved, leaving her heartbroken and dying to play football. She decides the only way she’ll be able to develop her skills and be taken seriously in the sport is to pose as her twin brother.
This elaborate plot takes her to college, where she joins the men’s football team and enters a tournament.
The movie is full of the same subjects as Clueless and is a fun teen comedy to watch whatever the occasion.
Oh, and remember Amanda Bynes? Yeah, she heads this movie alongside a young Channing Tatum.
Emma Roberts stars as a rebellious Malibu “princess” who’s sent to an extremely strict boarding school in England.
Unwilling to cooperate with the school’s rules, she refuses to accept the regime and misbehaves in the hope that she will be sent back to America.
It’s a fun coming-of-age American comedy set in England. It’s one the whole family can enjoy.
Alongside Emma Roberts are Adrian Quinn, Natasha Richardson, Lexi Ainsworth, and Shelby Young.
He’s All That
This movie came out in 2021 and is a remake of the 90s classic “She’s All That”, which I mentioned earlier in this article. However, as you’ve probably guessed from the name, the roles are reversed in this story.
Social media influencer Padgett and boyfriend Jordan break up on camera, and it goes viral on the internet.
Padgett decides she will give her high school’s least popular boy, Cameron, a makeover, turning him into the prom king.
If you enjoyed watching the teen drama in Clueless, you’ll enjoy this.
But, be warned, The Guardian News called the movie “Netflix’s dull TikTok teen remake”, so make of that what you will.
The movie stars Addison Rae, Madison Pettis, Tanner Buchanan, and Matthew Lillard.
Can’t Hardly Wait
Can’t Hardly Wait is your typical 90s American teen rom-com that you’ll love if you enjoyed watching Clueless.
It follows a mixed graduating class of good-looking girls, jocks, geeks, and rich kids… you know, all the usual types.
The mixed group meets at the rich kid’s house for a party. However, a lot happens at the party, including a planned confession of love and some other unplanned goings on.
The movie stars several young actors and actresses before they made it big such as Seth Green, Jennifer Love Hewitt, Ethan Embry, and Charlie Korsmo.
Not watched American Pie before? You need to, especially if you enjoyed watching Clueless. However, I must warn you, it’s a lot more graphic and basically revolves around sex.
In a bid to lose their virginity, four high school graduates Jim, Oz, Kevin, and Finch, make a pact to sleep with a woman before prom night ends.
The movie includes one memorable scene with an apple pie… but I’ll let you use your imagination for that one.
It stars Jason Biggs, Sean William Scott, Alyson Hannigan, and Chris Klein.