Many would consider the 1990s to be one of the best eras for teen comedies. Look no further than 1995's Clueless, which is a brilliant and hilarious film that perfectly captures that specific time while also holding up surprisingly well after all these years.
Clueless stars Alicia Silverstone as a popular rich girl who uses her powers of persuasion to become a matchmaker among her friends and teachers. The film explores the world of high school, the complexities of teen romance, and maintains a fun vibe throughout. It is the perfect movie to put you in a feel-good mood and luckily, there are plenty of other '90s classics that will give viewers that same feeling.
Emma (1996)
Some fans might not be aware that Clueless is actually loosely based on a Jane Austen novel called Emma. Oddly enough, one year after Clueless was released, Austen's novel got a more direct big-screen adaptation starring Gwyneth Paltrow.
Paltrow plays the titular 19th century Englishwoman who takes pleasure in acting as a matchmaker for her friends. But things get complicated when she begins considering a romance of her own. Emma and Clueless certainly have similarities, but both serve as their own unique interpretation of the same story.
Can't Hardly Wait (1998)
Every era's teen comedies need to have one party film and Can't Hardly Wait fills that role perfectly. Featuring an ensemble of young actors, including several who appear in Clueless, the film follows various characters as they attend a wild graduation party while looking to the future.
The real charm of the movie comes from these memorable characters, who represent various recognizable high school clichés. There are also some fun cameos peppered throughout the film.
American Pie (1999)
The decade ended with one of the biggest teen comedies of all time which inspired a whole new genre of sex comedies in the future. American Pie follows a group of male friends nearing the end of their high school days who make a pact to lose their virginities on prom night.
Clueless is a much more intelligent and subtle movie, but American Pie does deliver some big laughs with its crude humor. The iconic pie scene is still hilarious and Eugene Levy elevates the film as a perfect embarrassing dad.
Rushmore (1998)
Given that Rushmore is directed by Wes Anderson, it's no surprise that it doesn't quite fit alongside these other teen comedies. However, like Clueless, it is a clever and witty look at an ambitious and intelligent high school student who learns they don't have it as figured out as they thought.
Jason Schwartzman stars as a young man at a private high school who finds himself competing with his mentor for the affections of a charming young teacher. The movie is filled with Anderson's trademark dry humor and is an entertaining new take on the teen comedy.
Scream (1996)
While Scream falls more into the teen horror category than the teen comedy category, there is no denying it is a funny movie. It follows a group of young high schoolers being terrorized by a masked killer and picked off one by one.
The movie is an incredibly smart meta look at the slasher genre and is filled with funny and likable characters, many of whom meet bloody demises. But despite the blood, Scream feels at home with other '90s teen movies.
Dick (1999)
While Dick steps far outside the '90s era for its story, it still feels like a quintessential comedy from this time. The movie stars Kirsten Dunst and Michelle Williams as two airhead high school students who accidentally find themselves involved in the Watergate scandal.
The movie is a smart and hilarious imagining of how these lovable but not-too-bright characters might have changed the course of history forever. Also, Dan Hedaya, famous for playing Cher's dad in Clueless, plays Richard Nixon in this film.
Never Been Kissed (1999)
While Clueless has a popular and privileged character as its protagonist, Never Been Kissed looks at someone who didn't have such a fun time in high school. Drew Barrymore plays a reporter who is assigned to go undercover in high school, forcing her to relive her humiliating teen years.
Barrymore is effortlessly charming and funny in the lead role. She is also backed by a great cast who take this silly premise and turn it into a lovable romantic comedy that celebrates the outcasts of the world.
She's All That (1999)
There are few movies that feel as perfectly suited to the '90s teen comedy genre as She's All That. Starring a who's who of good-looking young actors from the era, it follows a popular jock who accepts a bet from his friends that he cannot transform a timid bookworm into the prom queen.
The cheesy premise is the perfect setup for an unexpected love story with plenty of drama and excitement. It has everything fans of the genre would want and remains a wonderfully rewatchable film of this kind.
Romy And Michele's High School Reunion (1997)
Clueless has a lot of fun with the over-the-top nature of its characters, which is something Romy and Michelle's High School Reunion embraces as well. Mira Sorvino and Lisa Kudrow star as the titular friends who come up with an elaborate lie to impress everyone at their 10-year high school reunion.
The two leads are hilarious as the dim-witted but loyal best friends. It is a total blast joining these two on their epic road trip while also seeing how high school never changes for some even after a decade of leaving it behind.
10 Things I Hate About You (1999)
Just as Clueless borrowed from classic source material, 10 Things I Hate About You is a modern telling of William Shakespeare's Taking of the Shrew. Joseph Gordon Levitt plays a young man hoping to ask out a pretty classmate (Larisa Oleynik) only to discover she can't date until her older sister (Julia Stiles) does. Gordon-Levitt then hires bad boy Heath Ledger to ask out the older sister.
The talented young cast and the amusingly complicated plot make for a really fun time. Ledger showed off his early charisma and brought a lot of fun to the role while the story has some great genre moments.