1995 | 1 hour 37 minutes | Directed by Amy Heckerling
 

Starry Alicia Silverstone, Stacey Dash, Brittany Murphy

There are many cases when a book-based movie turns sour, but Clueless is a stellar example of how such a movie should look and feel, I daresay. Loosely based on Jane Austen's 1815 novel Emma, Clueless is considered one of the greatest teen romantic comedies ever made. The film's success propelled young Alicia Silverstone's career and had us all swooning for Paul Rudd, adopting the "As if!" and wishing for the dazzling outfits from Cher's and Dionne's closets.

1990 | 1 hour 25 minutes | Directed by John Waters
 

Starring Johnny Depp, Ricki Lake, Amy Locane

Cry-Baby is a romantic musical comedy directed by John Waters. Yes, the same John Waters of Pink Flamingos infamy. Set in 1950s Baltimore, it follows a love story that goes like this - a bad boy with a heart of gold falls for a good girl with a bad boyfriend, which ultimately ends in a fight between good and bad. So, lots of goods and lots of bads, and a whole lot of entertaining! Cry-Baby is an ode to the teen rebellion and one that's more than swell at doing its job.

1998 | 2 hours 4 minutes | Directed by Gary Ross
 

Starring Tobey Maguire, Jeff Daniels, Joan Allen

Pleasantville is a fantasy comedy-drama that follows two teenage siblings who find themselves trapped in a 1950s sitcom. The life of the small Midwest town they end up in seems absolutely perfect, and the people living there - impeccably happy. However, that soon turns out to be false, and the influence of the TV show starts to seep into the teenagers' real ones. Pleasantville is a lighthearted satire that knows exactly how to entertain the audience.

1993 | 1 hour 43 minutes | Directed by Richard Linklater
 

Starring Jason London, Wiley Wiggins, Matthew McConaughey 

Dazed And Confused is yet another cult classic comedy/coming-of-age story on our list; it seems that the '90s spawned plenty of iconic movies! So, here, we get to follow the adventures of high school and junior high students on their last day of school in 1976, and, boy, do they get wild! From sketchy characters to off-the-wall happenings, Dazed And Confused will take you to the whirlwind that is teenage life. By the way, it's one of Tarantino's favorite movies, and that's a great recommendation.

1999 | 1 hour 43 minutes | Directed by Alexander Payne
 

Starring Matthew Broderick, Reese Witherspoon, Chris Klein

Election is a black comedy film based on Tom Perrota's 1998 novel of the same name. The election mentioned in the movie's name is actually an election for a high school Class President title, and there's one clear favorite - Tracy Flick. However, not everybody is happy with her, so a teacher convinces a bona fide jock to run against her. This, of course, sparks a very interesting chain of events. Election, with its combination of dark humor and intelligent writing, is one heck of a witty and entertaining movie!

1996 | 1 hour 51 minutes | Directed by Wes Craven
 

Starring Neve Campbell, Courteney Cox, David Arquette

Scream is, as you all well know, a slasher film that follows teenager Sidney as she and her friends start to get weird calls one year after Sidney's mother's death. The team soon figures out that the calls are coming from a crazed serial killer, and here's when the slashing and the gore and all the good stuff start. Scream created such a craze among the audiences that to this day, even with an adjusted dollar rate, it is still the highest-grossing slasher film ever made. And if that isn't a guarantee of a great time, we don't know what is!

1990 | 1 hour 50 | Directed by Richard Benjamin
 

Starring Cher, Bob Hoskins, Winona Ryder

Mermaids is a family comedy-drama film based on Patty Dan's 1986 novel of the same name. Set in the 1960s, it follows a crazed teenager who moves in with her wayward mother and a younger sister to a small town in Massachusetts. The teen in question rebels against her mother's debaucheries and becomes infatuated with all things Catholic, even dreaming of becoming a nun. However, in the end, the two of them learn to accept each other and even change for the better. Mermaids is a fun movie about the serious thing called growing up; also, add in the Cher factor, and it is even better.

1990 | 1 hour 40 minutes | Directed by Reginald Hudlin
 

Starring Christopher Reid, Robin Harris, Christopher Martin

House Party is a definite cult classic comedy that follows the events that happened at… a house party. The two best friends had hoped for an all-out party, yet what they actually got was the wildest night of their lives. House Party is full of iconic slapstick comedy, witty lines, and an atmosphere that's the absolute embodiment of the '90s. And, even if you watch this movie for the first time as an adult, you'll still feel the urge to find the nearest house party and sneak into it.

1998 | 1 hour 33 minutes | Directed by Wes Anderson
 

Starring Bill Murray, Jason Schwartzman, Olivia Williams

Rushmore is a coming-of-age comedy-drama film directed by Wes Anderson before Wes Anderson the Pastels Man emerged. Of course, despite the lack of pastels, it is still a very kooky movie, following the story of a Rushmore Academy student falling for a much older teacher and befriending a middle-aged industrialist. Soon, our diligent student figures out that the teacher and his friend are having an affair, which sparks a full-out vendetta from him. Rushmore is definitely a very original take on 'teenage' movies that will amuse the heck out of you with its unconventional story and humor.

1990 | 1 hour 42 minutes | Directed by Allan Moyle
 

Starring Christian Slater, Samantha Mathis, Anthony Lucero

Pump Up The Volume is a coming-of-age comedy-drama film that follows the story of a high school student named Mark. He runs a pirate radio station entertaining his fellow youth; however, once he starts to use the said station as a vessel for speaking his mind, a real uproar begins among his teen comrades. However fun the premise of Pump Up The Volume might sound, it did not become a box office hit. Nevertheless, the critics loved it, and so did the audiences later on! So much so, in fact, that this movie even got adapted into a musical.