Entertainment
There are many movies like 'Clueless' fans can watch to celebrate the film's 25th anniversary.

If You Love 'Clueless' You're Going To Be Totally Buggin' Over These Movies

by Dylan Kickham
Paramount Pictures

It's been 25 years since Cher Horowitz first donned her yellow plaid blazer and uttered the brutal kiss-off that's still iconic to this day: "As if!" Everyone who loves a good teen movie will tell you that Clueless really is the paramount of quotable, fashionable, rom-com goodness, and chances are you've rewatched it so many times you can recite the whole script by heart. If you want to try something new with a similar vibe, these movies like Clueless that are available to stream are your best bets.

On July 19, 2020, Clueless officially celebrated its 25th anniversary. The classic teen comedy first hit theaters in the summer of 1995, and has become one of the most emblematic films of the decade in terms of both linguistics and fashion. It launched the movie careers of Alicia Silverstone and Brittany Murphy, and was also Paul Rudd's first major movie role ever. While the story of a seemingly airheaded Valley girl with undeniable charm and a knack for makeovers seems inextricably tied to the '90s, Clueless also has a timeless quality as an adaptation of Jane Austen's 1815 novel Emma.

There are a ton of other great movies that capture the bratty, campy, heart-on-its-sleeve charm of Clueless, so check these out next time you're craving a funny, comforting teen comedy:

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1. Emma

Miramax Films

Where to stream: HBO Max

If Clueless feels timeless, that's because it's loosely based on the Jane Austen novel Emma. The story of the plucky young noblewoman Emma Woodhouse is basically the same as Cher's, just set in 19th-century England rather than Beverly Hills. Gwyenth Paltrow stars in the 1996 theatrical adaptation of Emma that was released just one year after Clueless. There's also a newer version of Emma starring Anya Taylor-Joy that was released in 2020, which is available to rent for $5.99 on Amazon.

2. What a Girl Wants

Where to stream: Netflix

Tai may have felt like a fish out of water in Clueless, but that's nothing compared to Daphne's unexpected foray into British aristocracy. The 2003 Amanda Bynes movie has a lot in common with Clueless, including an undeniably likable (if a bit ditzy at times) teen lead, an adorable romance, and an impossibly elegant mansion.

3. Heathers

Where to stream: Hulu

If Clueless has become a poster child of '90s teen movies, then Heathers is the paragon of the '80s. The 1989 black comedy also centers on a transformative makeover to turn an outcast into one of the most popular girls in school, except there's a lot more murder involved. Still, Heathers has stood the test of time along with Clueless as one of the most quotable high school classics ever made.

4. Election

Where to stream: Amazon Prime

Cher may seem clueless, but she actually does strive to get high marks in school and knows exactly how to get what she wants, and that's a spirit of determination she shares with Election's Tracy Flick. The 1999 Reese Witherspoon comedy my not be quite as lighthearted as Clueless, but it delivers just as many laughs and memorable moments.

5. 10 Things I Hate About You

Buena Vista Pictures

Where to stream: Disney+

The happy-go-lucky, materialistic Cher Horowitz may be the complete opposite of the patriarchy-dismantling Kat Stratford, but strangely enough, their stories about finding love and discovering their true selves in high school are very similar. Plus, both films star iconic '90s actors and are based on prestigious works — 10 Things I Hate About You is an adaptation of Shakespeare's The Taming of the Shrew.

6. Josie and the Pussycats

Where to stream: HBO Max

If your favorite aspect of Clueless is the movie's campy silliness, then Josie and the Pussycats needs to be the next title on your watch list. The 2001 musical comedy celebrates early 2000s fashion and lingo in the same way Clueless did for the '90s. Plus, both movies have a similar unexpected moral about the dangers of consumerism. Oh, and there are also a couple actors in common: Donald Faison and Breckin Meyer graduated as Clueless high schoolers to make up half of the doomed boy band Du Jour in Josie and the Pussycats.

7. The Edge of Seventeen

Where to stream: Netflix

Cher and Josh's tempestuous step-sibling relationship is nothing compared to the complex resentment of Nadine for her older, more popular brother Darian in The Edge of Seventeen. Just like Clueless, the 2016 Hailee Steinfeld movie explores how it feels to be betrayed by a best friend, except Nadine says a lot more than just "That was way harsh, Tai."

8. Drop Dead Gorgeous

Where to stream: HBO Max

One of the primary reasons Clueless has remained so beloved years later is all of its quotable lines, and that's also what made Drop Dead Gorgeous a cult classic. The 1999 black comedy nails the same type of ditzy-but-smart humor that made Clueless a hit, and it also stars Brittany Murphy as an outsider-type character who feels pretty similar to Tai. As an added bonus, the beloved beauty pageant mockumentary is filled with a ton of other major actors in early roles, like Kirsten Dunst and Amy Adams.

9. Lady Bird

Where to stream: Netflix

Cher has her fair share of boy problems in Clueless, and Lady Bird can definitely relate. Both teenagers have no trouble standing out with their unique names and flair for dramatics; plus, they share a home state (although Lady Bird lives considerably further north). All in all, the Saoirse Ronan-led 2017 movie is a more modern and moodier choice for Clueless fans, but it still hits the spot.

10. Romy and Michele's High School Reunion

Buena Vista Pictures

Where to stream: $2.99 to rent on Amazon

If you're a fan of the bold, colorful, sometimes bordering-on-ridiculous fashion choices in Clueless, you'll be all over the outfits in Romy and Michele's High School Reunion. The flashy fashion sense isn't the only DNA these two movies share, though. Much like Cher, both Romy and Michele come off as ditzy Valley girls at first, but they prove themselves to be clever, smart, and kind throughout their trip to their high school reunion. Unfortunately, the movie isn't available to stream for free, but you can rent a digital copy for cheap on Amazon.

11. A Cinderella Story

Where to stream: HBO Max

For people who swoon over the love stories in Clueless, A Cinderella Story is the perfect follow-up to check out to get your teen movie romance fix. A modern adaptation of Cinderella, the Hilary Duff flick employs online chatrooms and a masquerade ball to keep the identity of Sam's secret love (Chad Michael Murray, of course) hidden from her. Not only is it a great romance, but it also encapsulates so much mid-2000s nostalgia in a similar way that Clueless does for the '90s.

Honestly, if you love Clueless, then you have probably also watched a good chunk of these fun teen comedies, but hopefully there will be a couple you haven't seen yet that you can enjoy for the first time. Or, of course, you can just put on Clueless again — it's streaming on Netflix, so there's nothing stopping you from rewatching it as often as you like.