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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)
14%

#17
Adjusted Score: 16609%
Critics Consensus: This throwaway comedy falls victim to its hip sensibilities.
Synopsis: When an exclusive clique of teenage socialites accidentally murders their best friend, Liz (Charlotte Ayanna), on the morning of her... [More]
Starring: Rose McGowan, Rebecca Gayheart, Julie Benz, Judy Greer
Directed By: Darren Stein

#16

Idle Hands (1999)
16%

#16
Adjusted Score: 18159%
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: When slacker teen Anton Tobias (Devon Sawa) has his right hand possessed by a demonic force, he finds that his... [More]
Starring: Devon Sawa, Seth Green, Elden Henson, Jessica Alba
Directed By: Rodman Flender

#15
#15
Adjusted Score: 21892%
Critics Consensus: As a dark comedy-thriller, this movie lacks humor and thrill.
Synopsis: A hardworking and bright high-school senior, Leigh Ann (Katie Holmes) has her impending status as valedictorian jeopardized when her bitter... [More]
Starring: Helen Mirren, Katie Holmes, Jeffrey Tambor, Barry Watson
Directed By: Kevin Williamson

#14
#14
Adjusted Score: 24199%
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: When her closest friend commits suicide after being manipulated by the popular crowd, quiet and bookish Rachel Lang (Emily Bergl)... [More]
Starring: Emily Bergl, Jason London, Dylan Bruno, J. Smith-Cameron
Directed By: Katt Shea

#13

Drive Me Crazy (1999)
29%

#13
Adjusted Score: 30143%
Critics Consensus: Unoriginal story.
Synopsis: Nicole (Melissa Joan Hart) and Chase (Adrian Grenier) live next door to each other but are worlds apart. However, they... [More]
Starring: Melissa Joan Hart, Adrian Grenier, Susan May Pratt, Kris Park
Directed By: John Schultz

#12

She's All That (1999)
41%

#12
Adjusted Score: 43552%
Critics Consensus: Despite its charming young leads, She's All That can't overcome its predictable, inconsistently funny script.
Synopsis: High school hotshot Zach Siler (Freddie Prinze Jr.) is the envy of his peers. But his popularity declines sharply when... [More]
Starring: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker
Directed By: Robert Iscove

#11

Varsity Blues (1999)
45%

#11
Adjusted Score: 47270%
Critics Consensus: This is a predictable football movie that lacks intensity.
Synopsis: In West Canaan, Texas, high school football reigns supreme. When starting quarterback Lance Harbor (Paul Walker) turns up injured, the... [More]
Starring: James Van Der Beek, Jon Voight, Paul Walker, Ron Lester
Directed By: Brian Robbins

#10
#10
Adjusted Score: 50172%
Critics Consensus: It's dark humor sometimes hits, but mostly misses the target.
Synopsis: An annual beauty pageant in small-town Minnesota turns ridiculously competitive and ultimately chaotic in this biting comedy. Amber Atkins (Kirsten... [More]
Starring: Kirsten Dunst, Ellen Barkin, Allison Janney, Denise Richards
Directed By: Michael Patrick Jann

#9
#9
Adjusted Score: 51368%
Critics Consensus: Silly plot, over-the-top directing style.
Synopsis: Rock-loving teens and aspiring musicians Hawk (Edward Furlong), Lex (Giuseppe Andrews), Trip (James DeBello) and Jam (Sam Huntington) can't wait... [More]
Starring: Edward Furlong, Giuseppe Andrews, James DeBello, Sam Huntington
Directed By: Adam Rifkin

#8
#8
Adjusted Score: 55342%
Critics Consensus: Miscasted performers and humor miss the mark.
Synopsis: In this coming-of-age comedy, Tim Dunphy (Shawn Hatosy) is leading a go-nowhere existence, spending his days smoking pot and hanging... [More]
Starring: Shawn Hatosy, Jon Abrahams, Tommy Bone, Jonathan Brandis
Directed By: Michael Corrente

#7

Cruel Intentions (1999)
54%

#7
Adjusted Score: 59597%
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: Annette (Reese Witherspoon) unwittingly becomes a pawn in Sebastian's (Ryan Phillippe) and Kathryn's (Sarah Michelle Gellar) deliciously diabolical wager of... [More]
Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Directed By: Roger Kumble

#6
#6
Adjusted Score: 59187%
Critics Consensus: Drew Barrymore's effervescent charm is almost enough to make you forgive this teen comedy's incredibly silly storyline.
Synopsis: Josie Geller (Drew Barrymore), a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former... [More]
Starring: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Directed By: Raja Gosnell

#5

American Pie (1999)
61%

#5
Adjusted Score: 67274%
Critics Consensus: So embarrassing it's believable, American Pie succeeds in bringing back the teen movie genre.
Synopsis: A riotous and raunchy exploration of the most eagerly anticipated -- and most humiliating -- rite of adulthood, known as... [More]
Starring: Jason Biggs, Shannon Elizabeth, Alyson Hannigan, Chris Klein
Directed By: Paul Weitz

#4

The Wood (1999)
61%

#4
Adjusted Score: 63214%
Critics Consensus: A charming piece of work with believable characters.
Synopsis: Three old friends -- Mike (Omar Epps), Roland (Taye Diggs) and Slim (Richard T. Jones) -- recount memories of their... [More]
Starring: Omar Epps, Taye Diggs, Richard T. Jones, Sean Nelson
Directed By: Rick Famuyiwa

#3
#3
Adjusted Score: 75302%
Critics Consensus: Julia Stiles and Heath Ledger add strong performances to an unexpectedly clever script, elevating 10 Things (slightly) above typical teen fare.
Synopsis: Kat Stratford (Julia Stiles) is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn't... [More]
Starring: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Directed By: Gil Junger

#2

Dick (1999)
72%

#2
Adjusted Score: 75172%
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: Betsy (Kirsten Dunst) and Arlene (Michelle Williams) are two 15-year-old girls in 1976. When Betsy visits Arlene at the Watergate... [More]
Starring: Kirsten Dunst, Michelle Williams, Jim Breuer, Will Ferrell
Directed By: Andrew Fleming

#1

Election (1999)
92%

#1
Adjusted Score: 97541%
Critics Consensus: Election successfully combines dark humor and intelligent writing in this very witty and enjoyable film.
Synopsis: Jim McAllister (Matthew Broderick), a well-liked high school government teacher, can't help but notice that successful student Tracy Flick (Reese... [More]
Starring: Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell
Directed By: Alexander Payne

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