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All 1999 Teen Movies Ranked

For moviegoers of a certain age, 1999 was a particularly fertile year for teen-centric films that spoke directly to the adolescent experience. Whether it was a rom-com like 10 Things I Hate About You, a biting satire like Election, a bawdy sex romp like American Pie, or a darkly comic drama like Cruel Intentions, there was a little something for everyone, and several of them went on to develop cult followings that hold strong to this day.

This year, all of those films celebrate their 20th anniversary, and to mark the occasion, we decided to take a quick little jog down memory lane and look at the whole batch of 1999 teen movies to see how they rank against each other. Are they really as good as you remember?

#17

Jawbreaker (1999)
8%

#17
Adjusted Score: 10.093%
Critics Consensus: This throwaway comedy falls victim to its hip sensibilities.
Synopsis: High school. A time of sweet innocence. Untainted youth. Goal-oriented teenagers. NOT! At fictional Reagan High School, these are the... [More]
Directed By: Darren Stein

#16

Idle Hands (1999)
16%

#16
Adjusted Score: 17.836%
Critics Consensus: An uneasy mix of slapstick and gore, Idle Hands lacks the manic energy and comedic inspiration required to pull off its goofy premise.
Synopsis: The devil will find work for idle hands to do, so what happens when he goes on the prowl for... [More]
Directed By: Rodman Flender

#15
#15
Adjusted Score: 21.609%
Critics Consensus: As a dark comedy-thriller, this movie lacks humor and thrill.
Synopsis: After the success of Scream, I Know What You Did Last Summer, and television's Dawson's Creek, screenwriter Kevin Williamson made... [More]
Directed By: Kevin Williamson

#14
#14
Adjusted Score: 20.804%
Critics Consensus: As disposable as its predecessor is indispensable, The Rage: Carrie 2 mimics the arc of Stephen King's classic story without adding anything of value.
Synopsis: In this film, the boys on the high-school football team compete to see who can seduce the most girls. When... [More]
Directed By: Katt Shea

#13

Drive Me Crazy (1999)
28%

#13
Adjusted Score: 28.856%
Critics Consensus: Unoriginal story.
Synopsis: Nicole and Chase live next door to each other ' and that's about all they have in common. Nicole is... [More]
Directed By: John Schultz

#12

She's All That (1999)
40%

#12
Adjusted Score: 42.093%
Critics Consensus: Despite its charming young leads, She's All That can't overcome its predictable, inconsistently funny script.
Synopsis: In the tradition of Clueless, Sixteen Candles and The Breakfast Club, comes a hilarious new comedy about sex, style and... [More]
Directed By: Robert Iscove

#11

Varsity Blues (1999)
41%

#11
Adjusted Score: 42.784%
Critics Consensus: This is a predictable football movie that lacks intensity.
Synopsis: In his 35th year as head coach, Bud Kilmer is trying to lead his West Canaan Coyotes to their 23rd... [More]
Directed By: Brian Robbins

#10
#10
Adjusted Score: 47.454%
Critics Consensus: It's dark humor sometimes hits, but mostly misses the target.
Synopsis: The local boosters of Mount Rose, Minnesota proudly invites you to watch as their annual celebration of civic pride, wholesome... [More]
Directed By: Michael Patrick Jann

#9
#9
Adjusted Score: 49.062%
Critics Consensus: Silly plot, over-the-top directing style.
Synopsis: Set in 1978, Detroit Rock City follows four teenagers who embark on a wild adventure to attend a KISS concert.... [More]
Directed By: Adam Rifkin

#8
#8
Adjusted Score: 53.867%
Critics Consensus: Miscasted performers and humor miss the mark.
Synopsis: Based on a novel by Peter Farrelly, published in 1988 before he became famous as a writer and director of... [More]
Directed By: Michael Corrente

#7

Cruel Intentions (1999)
54%

#7
Adjusted Score: 58.826%
Critics Consensus: This darkly comic drama and its attractive young cast are easy on the eyes, but uneven performances and an uninspired script conspire to foil Cruel Intentions.
Synopsis: Sarah Michelle Gellar and Ryan Phillippe sizzle as a pair of unscrupulous siblings in a deliciously sexy tale of seduction,... [More]
Directed By: Roger Kumble

#6
#6
Adjusted Score: 59.537%
Critics Consensus: Unoriginal and unremarkable high school satire adds little to the genre.
Synopsis: Many people wish they could go back to high school, knowing what they know as an adult; Josie Geller gets... [More]
Directed By: Raja Gosnell

#5

American Pie (1999)
61%

#5
Adjusted Score: 66.496%
Critics Consensus: So embarrassing it's believable, American Pie succeeds in bringing back the teen movie genre.
Synopsis: In this wild Unrated version of the hit comedy, follow the raging hormones of four teenage boys and their girls... [More]
Directed By: Paul Weitz

#4

The Wood (1999)
61%

#4
Adjusted Score: 62.939%
Critics Consensus: A charming piece of work with believable characters.
Synopsis: A man who's uncertain about the biggest step forward of his life steps back to take a look at his... [More]
Directed By: Rick Famuyiwa

#3
Adjusted Score: 70.867%
Critics Consensus: Julia Stiles and Heath Ledger add strong performances to an unexpectedly clever script, elevating 10 Things (slightly) above typical teen fare.
Synopsis: Popular, pretty Bianca Stratford (Larisa Oleynik) is in dilemma. A family rule forbids her from dating until her unpopular, rebellious,... [More]
Directed By: Gil Junger

#2

Dick (1999)
71%

#2
Adjusted Score: 73.712%
Critics Consensus: A clever, funny slice of alternate history, Dick farcically re-imagines the Watergate era and largely succeeds, thanks to quirky, winning performances from Michelle Williams, Kirsten Dunst and Will Ferrell.
Synopsis: In DICK, an historically-challenged comedy, high school students Betsy Jobs and Arlene Lorenzo wander off during a class trip to... [More]
Directed By: Andrew Fleming

#1

Election (1999)
92%

#1
Adjusted Score: 96.671%
Critics Consensus: Election successfully combines dark humor and intelligent writing in this very witty and enjoyable film.
Synopsis: In this satiric comedy, Jim McAllister is a popular and well-respected instructor at George Washington Carver High School in Omaha,... [More]
Directed By: Alexander Payne

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