ByColleen K. Brutz, writer at
Verified Creator who loves Corgis, animation, Batman, tattoos, punk music, comics, Rams football, musicals, and Super Smash Bros.
Colleen K. Brutz

It’s May, which means that high school is about to come to an end for those lucky Class of 2017 seniors. They’ve paid their dues, made it through the past four years, and finally get to move on from those awkward high school days.

Most of this year’s high school graduates were born in 1999. Coincidentally, that year was the peak of high school movies. The year 1999 had the most teen movies in a single year, even surpassing all years during the John Hughes era of the 1980s. The influx of high school movies in 1999 even prompted the spoof comedy, Not Another Teen Movie (2001), which poked fun at the crazy popularity of teen movies at that time. Here’s a list of teen movies from 1999 worth checking out.

8. 10 Things I Hate About You

'10 Things I Hate About You' [Credit: Buena Vista Pictures]
'10 Things I Hate About You' [Credit: Buena Vista Pictures]

Assignment: When a love-struck teenager finds out that his crush is only allowed to date when her ill-tempered older sister dates, he convinces the school’s popular rich kid to hire an outcast bad-boy to date her sister.

Student Body: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt and Larisa Oleynik

Extra Credit:

  • The story is based on William Shakespeare’s The Taming of the Shrew.
  • The film launched the careers of Julia Stiles, the late, great Heath Ledger and Joseph Gordon-Levitt.
  • 10 Things is arguably one of the greatest teen romantic comedies of all time.

7. American Pie

Assignment: A group of high school seniors make a pact to lose their virginity before graduation.

Student Body: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Eddie Kaye Thomas, Alyson Hannigan, Tara Reid, Mena Suvari, Seann William Scott, Shannon Elizabeth and Eugene Levy

Extra Credit:

  • The filmed famously coined the phrase, “One time at band camp…” and popularized the term “MILF.”
  • Pop punk band Blink-182 makes a cameo in the film.
  • Jason Biggs deserves mad props for his infamous pie scene, which gave the movie its title.

6. Drive Me Crazy

'Drive Me Crazy' [Credit:  Fox]
'Drive Me Crazy' [Credit: Fox]

Assignment: One of the school’s popular girls helps her estranged, misfit neighbor become popular to make their perspective romantic prey jealous.

Student Body: Melissa Joan Hart and Adrian Grenier

Extra Credit:

  • The film was Adrian Grenier’s first big role long before becoming Entourage’s Vincent Chase. Funnily enough, his character’s name is Chase in the film!
  • Britney Spears’s hit song “Crazy” was featured on the film’s soundtrack. Hart and Grenier were even in the music video for the song.
  • Girl band The Donnas have a cameo in the film.

5. Drop Dead Gorgeous

'Drop Dead Gorgeous' [Credit: New Line Cinema]
'Drop Dead Gorgeous' [Credit: New Line Cinema]

Assignment: A teenage girl from a Podunk Minnesota town competes in a beauty pageant, during which several contestants mysteriously die.

Student Body: Kirsten Dunst, Denise Richards, Kirstie Alley, Ellen Barkin and Allison Janney

Extra Credit:

  • The story is told in a mockumentary format.
  • Academy Award nominee Amy Adams made her acting debut in the film.
  • The dark comedy is now regarded as a cult film.

4. Idle Hands

'Idle Hands' [Credit: Columbia Pictures]
'Idle Hands' [Credit: Columbia Pictures]

Assignment: When news of a killer takes over a small town, a teenage stoner discovers that his murderous hand is possessed by the devil. But when he cuts the hand off and the hand roams free, he and his zombie friends race to stop it from continuing its killing spree and taking his girlfriend to hell.

Student Body: Devon Sawa, Seth Green, Elden Henson, Jessica Alba and Vivica A. Fox.

Extra Credit:

  • The horror comedy was a box office flop but has since acquired its status as a cult film.
  • Punk band The Offspring has a cameo in the film. The band’s lead vocalist and guitarist, Dexter Holland, is even scalped and killed by the possessed hand in the Halloween dance scene.

3. Jawbreaker

'Jawbreaker' [Credit: TriStar Pictures]
'Jawbreaker' [Credit: TriStar Pictures]

Assignment: A birthday prank goes awry when a group of girls accidentally kill their friend and most popular girl in school. But when a lonely outcast discovers their secret, the girls offer to transform her into one of them in order to keep her quiet.

Student Body: Rose McGowan, Rebecca Gayheart, Julie Benz and Judy Greer

Extra Credit:

  • The film is often compared to its predecessor, Heathers (1988), and its successor, Mean Girls (2004).
  • Singer Marilyn Manson, who was engaged to Rose McGowan at the time, has a cameo in the film, but not as a musician like those with cameos listed above.

2. Never Been Kissed

Assignment: A 25-year-old copy editor for the Chicago Sun-Times (and former high school loser) gets her first big assignment: Go back to high school undercover and find the next big story.

Student Body: Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski, Jeremy Jordan, Molly Shannon, Garry Marshall and John C. Reilly.

Extra Credit:

  • The film was Academy Award nominee James Franco’s movie debut. Jessica Alba also played a minor character as a high schooler.
  • The film is generally perceived as a sweet romantic comedy despite its nonchalant stance on the touchy subject of student-teacher relationships.

1. She’s All That

Assignment: A popular high school jock makes a bet that he can turn an artsy outcast into the school’s next prom queen.

Student Body: Freddie Prinze, Jr., Rachael Leigh Cook, the late, great Paul Walker, Elden Henson, Jodi Lyn O'Keefe, Anna Paquin and Matthew Lillard

Extra Credit:

  • Musical artists Usher and Lil’ Kim both play minor characters in the film.
  • Sarah Michelle Gellar, who was then dating Freddie Prinze, Jr., has a small non-speaking and uncredited cameo in the movie, despite being a hugely popular star at the time.
  • The film is the most parodied teen movie in the aforementioned spoof, Not Another Teen Movie.

That’s not all! Other teen movies from 1999 include: Cruel Intentions, Election, Varsity Blues and The Virgin Suicides, making it the year that 12 high school movies were released — one for each grade leading up to graduation!

Have you seen all of these high school movies from 1999? Which one is your favorite? Are there any teen movies missing from this list? Let us know in the comments below.


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