Teen movies that came out in 1999
by tbell1826 | created - 03 Apr 2018 | updated - 03 Apr 2018 | Public- Instant Watch Options
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1. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 385,784 | Gross: $38.18M
2. Cruel Intentions (1999)
R | 97 min | Drama, Romance
Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
Director: Roger Kumble | Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Votes: 205,309 | Gross: $38.77M
3. She's All That (1999)
PG-13 | 95 min | Comedy, Romance
A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.
Director: Robert Iscove | Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker
Votes: 103,882 | Gross: $63.37M
4. American Pie (1999)
R | 95 min | Comedy
Four teenage boys enter a pact to lose their virginity by prom night.
Directors: Paul Weitz, Chris Weitz | Stars: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Jennifer Coolidge
Votes: 434,051 | Gross: $102.56M
5. Varsity Blues (1999)
R | 106 min | Comedy, Drama, Romance
A back-up quarterback is chosen to lead a Texas football team to victory after the star quarterback is injured.
Director: Brian Robbins | Stars: James Van Der Beek, Jon Voight, Paul Walker, Ron Lester
Votes: 49,110 | Gross: $52.89M
6. The Virgin Suicides (1999)
R | 97 min | Drama, Romance
A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents in suburban Detroit in the mid 1970s.
Director: Sofia Coppola | Stars: Kirsten Dunst, Josh Hartnett, James Woods, Kathleen Turner
Votes: 169,367 | Gross: $4.86M
7. Jawbreaker (1999)
R | 86 min | Comedy, Crime, Thriller
Three of the most popular girls at Reagan High accidentally kill the prom queen with a jawbreaker when a kidnapping goes horribly wrong.
Director: Darren Stein | Stars: Rose McGowan, Rebecca Gayheart, Julie Benz, Alexandra Adi
Votes: 28,969 | Gross: $3.07M
8. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 97,623 | Gross: $55.47M
9. Drive Me Crazy (1999)
PG-13 | 91 min | Comedy, Drama, Romance
Nicole and Chase used to be BFFs, then junior high happened. The high school centennial dance is coming but Nicole gets dumped. So does Chase. They stage a relationship to get at their exes. They visit each other's worlds. Love in the air?
Director: John Schultz | Stars: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Mark Metcalf
Votes: 21,308 | Gross: $17.85M
10. But I'm a Cheerleader (1999)
R | 85 min | Comedy, Drama, Romance
A naive teenager is sent to rehab camp when her straitlaced parents and friends suspect her of being a lesbian.
Director: Jamie Babbit | Stars: Natasha Lyonne, Clea DuVall, Michelle Williams, Brandt Wille
Votes: 41,295 | Gross: $2.21M
11. Idle Hands (1999)
R | 92 min | Comedy, Fantasy, Horror
A teenage slacker's right hand becomes possessed with murderous intent.
Director: Rodman Flender | Stars: Devon Sawa, Seth Green, Elden Henson, Jessica Alba
Votes: 46,783 | Gross: $4.00M
12. Detroit Rock City (1999)
R | 95 min | Adventure, Comedy, Music
In 1978, four rebellious teenagers try to scam their way into a KISS concert.
Director: Adam Rifkin | Stars: Edward Furlong, Giuseppe Andrews, James DeBello, Sam Huntington
Votes: 41,370 | Gross: $4.22M
13. Dick (1999)
PG-13 | 94 min | Comedy
After wandering off during a White House tour, two high school girls inadvertently become Richard Nixon's top secret advisers at the height of the Watergate scandal.
Director: Andrew Fleming | Stars: Kirsten Dunst, Michelle Williams, Dan Hedaya, Will Ferrell
Votes: 21,376 | Gross: $6.24M
14. Drop Dead Gorgeous (1999)
PG-13 | 97 min | Comedy, Romance, Thriller
A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win.
Director: Michael Patrick Jann | Stars: Kirsten Dunst, Denise Richards, Ellen Barkin, Allison Janney
Votes: 40,851 | Gross: $10.56M
15. The Rage: Carrie 2 (1999)
R | 104 min | Drama, Horror, Sci-Fi
A horrible massacre strikes up after an outcast teenage girl is taunted by a group of high school jocks, all of them unaware of her cutthroat telekinetic powers.
Directors: Katt Shea, Robert Mandel | Stars: Emily Bergl, Jason London, Dylan Bruno, J. Smith-Cameron
Votes: 17,896 | Gross: $17.76M
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