The ‘90s was a competitive time for great teen movies, and not all the hits have aged well, but there are some notable exceptions. Case in point: About 28 years have passed since the Beverly Hills high school classic known as Clueless was in theaters, and its lighthearted pace, comedic timing, bubblegum fashion and silly catchphrases — ”As if!” — still make for fun viewing.
Amy Heckerling’s 1995 film, which stars Alicia Silverstone, Stacey Dash and the late Brittany Murphy, was later made into a three-season TV series that ran on ABC and UPN with most of the cast except Silverstone. The TV show doesn’t appear to be available to watch online, but the original movie is available to stream right now on Paramount Plus.
If you’re in the mood for more movies like Clueless after rewatching it, we’ve got some top picks to consider that are available on some of the best streaming services. Some are likely to be surprising in how they are connected, but you’ll quickly catch the vibe.
Mean Girls (2004)
When the previously-homeschooled-in-Africa Cady (Lindsay Lohan) starts attending a Midwestern high school, she quickly learns that a group of popular girls called the Plastics (Rachel McAdams, Lacey Chabert and Amanda Seyfried) rule the roost. The Plastics decide to take Cady on as a project, and it is painfully funny to watch.
Another teen movie hall of famer, the Tina Fey-penned classic still elicits overt laughs and remains the comedic highlight of Lohan’s acting career. Likewise, McAdams’ Regina George character remains the quintessential example of a bully. And the soundtrack will transport you right back to the early Aughts. Check out our fun list of the best movies like Mean Girls, if you want to hop into another rabbit hole and be really fetch.
Watch on Netflix
On the surface, Emma. and Clueless don’t resemble each other. Their respective comedic paces are centuries apart, as are the time periods in which they take place. But both movies have the same inspiration in Jane Austen’s 1815 novel Emma, which is about a wealthy girl who likes to play matchmaker.
2020’s Emma. — yes, the period is part of the title — is a remake of the 1996 film of the same name, which starred Gwyneth Paltrow. The newer version stars Anya Taylor-Joy as Emma Woodhouse, and it’s the one to watch.
Watch on Peacock
The Half of It (2020)
Ellie Chu, a queer Chinese-American student played by Leah Lewis, writes other kids’ homework for money. Her hustle, which is needed to help pay the bills at home, leads her to take on a special project: helping jock Paul Munsky (Daniel Diemer) craft messages that will win over Aster Flores (Alexxis Lemire), the girl of his dreams. And, as it turns out, Ellie’s dreams, too.
The Cyrano de Bergerac premise is stronger here than in Clueless, and The Half of It has some dramatic elements to it, which Clueless definitely does not. But both show what happens when you awkwardly try to rig the dating game.
Watch on Netflix
Easy A (2010)
Nathaniel Hawthorne’s 19th century novel The Scarlet Letter serves as a loose inspiration for this comedy starring Emma Stone, Amanda Bynes and Penn Badgeley. Olive Pendergast is a gutsy student whose motto is, “Let’s not and say we did,” because boys pay her to be able to make up a lie and say that they have gone all the way with her.
Olive yearns for a life that is like an ‘80s movie montage, and Easy A references classic teen movies all throughout the film, connecting it with a strong lineage of stories. Lisa Kudrow’s twisted guidance counselor Mrs. Griffith is way more scandalous than her Friends character Phoebe Buffay could ever dream of being, and it’s bittersweet to watch Bynes give an incredible performance as Marianne, a pious cult leader in training, because the troubled star unfortunately hasn’t done a movie since.
Watch on Netflix
Turn the intensity dial up on Cher Horowitz and you get Tracy Flick, the overachieving student body president candidate with questionable scruples played to the hilt by Reese Witherspoon. Many movies that followed have turned school election plots into a trope, but this one is still a battle worth catching.
Election came out four years after Clueless and furthers its over-the-top cadence with some truly outrageous moments. These come largely courtesy of Witherspoon and Matthew Broderick, who plays Jim McAllister, the high school’s government teacher who couldn’t be further from Ferris Bueller, his daydreaming teen character from classic ‘80s flick. Whether you’re seeing Election for the first time or just the first time in awhile, prepare to be surprised at some of the twists along the way.
Watch on Max
But I’m a Cheerleader (1999)
Gay conversion camps get deliciously raked over the coals in this strong comedy starring Natasha Lyonne, Clea DuVall and Michelle Williams. Lyonne plays Megan, a cheerleader whose friends and family stage an intervention because they think she’s a lesbian. They send her to a camp called True Directions in order to, um, set her straight.
Lyonne is riveting as Megan comes to a big realization about herself, and RuPaul is wonderful as Mike, a counselor who is also a graduate of the program, yet still seems to delight in the male form. Like Election, But I’m a Cheerleader came out in 1999 and is a lot edgier than Clueless, yet they work so well together as companion viewing. The ‘90s moved fast!
Watch on Freevee
The Breakfast Club (1985)
John Hughes’ masterpiece offers the ultimate ‘80s ensemble cast in Molly Ringwald, Judd Nelson, Ally Sheedy, Emilio Estevez and Anthony Michael Hall. As they would come to describe themselves, “A brain, an athlete, a basket case, a princess and a criminal” convene for high school detention, which is the only way they would ever have interacted with each other. But over the course of the day, they form an incredible connection.
Clueless is a lot bubblier and more airheaded than the more aloof Gen X humor of The Breakfast Club, but they’re still a perfect pairing. After all, the Breakfast Club is still one of the most special stories to witness in the teen movie canon.
Watch on Netflix
Can’t Buy Me Love (1987)
Patrick Dempsey is adorable as Ronald Miller, a nerd in desperate need of a glow-up, in Can’t Buy Me Love. To help boost his status, Ronald pays a popular blonde named Cindy Mancini (Amanda Peterson) $1,000 to pretend she’s his girlfriend, and some very ‘80s teen movie shenanigans ensue.
Of course, Can’t Buy Me Love doesn’t represent the pinnacle of Dempsey’s long career, but it sure is a delight to watch now. It’s also fun to see the performance from a then-12-year-old Seth Green, who appears as Ronald’s wisecracking little brother Chuckie. And the soundtrack is truly diverse, spanning from soul sensations Atlantic Starr and the fleeting British pop band Curiosity Killed the Cat to the enduring punk pop OG Billy Idol.
Watch on Tubi