17 Best Teen Comedy Movies of 1999 — the Greatest Year for Adolescent Comedies

In January of 1999, two teen movies opened back to back and kicked off what would be one of the most extraordinary years for youth-oriented movies in the history of Hollywood. Both were No. 1 at the box office their first weekend. Both boasted remarkable casts of rising stars — they even shared a star in Paul Walker. And both whipped ancient genre conventions into new combinations that made them fresh and new. Yet for all their similarities, “Varsity Blues” and “She’s All That” couldn’t have been more different: one an R-rated sports drama that tempered its inspirational coming-of-age drama with surprisingly harsh depictions of misogyny and physical and mental abuse, the other a sweet, good-natured romantic comedy nearly as innocent as a Mickey Rooney-Judy Garland vehicle from the 1940s. In their similarities and differences lies the key to why 1999 was such a great year for movies of their type — the 1939 of teen movies.

The year was, as documented in Brian Raftery’s book “Best. Movie. Year. Ever.” and elsewhere, an incredible year for American cinema in general, yielding a broad range of classics that included “Magnolia,” “Eyes Wide Shut,” “Three Kings,” “Being John Malkovich,” “The Sixth Sense,” “Boys Don’t Cry,” “Fight Club,” “The Matrix,” and many more. What’s amazing is how much breadth there was not just across but even within genres and subgenres; we not only had great movies of nearly every kind, but a wide variety of each from which to choose. And everything seemed to be just a little better than normal; 1999 was a great year for meat-and-potatoes thrillers like “Double Jeopardy” and escapist adventure films like “Deep Blue Sea.” Almost every movie year has its masterpieces, but what makes 1999 exceptional is that even the programmers were terrific.

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The slate of teen movies that came out that year had both the masterpieces (“Election”) and the terrific programmers (“American Pie”). There were filmmakers like Alexander Payne and Andrew Fleming (“Dick”) who used the genre as a Trojan horse to comment on larger societal issues, and filmmakers like Katt Shea (“The Rage: Carrie 2”) who took unpromising studio assignments and turned them into vehicles of personal expression. There were visions of suburban life that were carefree (“Drive Me Crazy”) and horrifying (“American Beauty”), and world views generous (“10 Things I Hate About You”) and cynical (“Drop Dead Gorgeous,” “Jawbreaker,” “Cruel Intentions”). What all of these movies had in common was that they took teenage characters and audiences seriously in a way that John Hughes had 15 years earlier; even the silliest of the 1999 teen movies was written, directed, and acted with a degree of commitment that put youth film cycles of earlier eras — the beach party movies of the 1960s, or the “Porky’s” knockoffs of the early ’80s — to shame.

Something else they had in common was their actors. So many of the same performers show up in these movies that they form an unofficial repertory company, providing resonant links from one movie to the next. Kirsten Dunst, Mena Suvari, and Marissa Winokur each appeared in at least three of the movies on this list, and a huge number of actors — Walker, Reese Witherspoon, Chris Klein, Sarah Michelle Gellar, Ali Larter, and many others — show up in at least two. Some of the adult actors cross over from film to film too; Allison Janney shows up in “10 Things I Hate About You,” “American Beauty,” and “Drop Dead Gorgeous,” the latter of which also features a hilarious performance by “Election” vice principal Matt Malloy. Like Suvari, John Cho appears in both “American Pie” and “American Beauty,” and even an actor who only shows up in one 1999 teen movie, Matthew Broderick, carries associations from his own iconic high school role as Ferris Bueller. “Jawbreaker” and “Drive Me Crazy” even share the same prom band, ’90s rock and roll titans The Donnas.

The cumulative effect of all of this is to create a sense that the teen movies of 1999 are interconnected on a kind of subliminal level, even though they were made more or less concurrently and couldn’t have influenced each other. Although they’re strikingly different, they feel like parts of one bigger movie — it’s as though each teen movie is its own storyline in an overarching epic ensemble narrative like Paul Thomas Anderson’s “Magnolia,” one of 1999’s greatest films. To watch all of them together is both an illuminating and slightly exhausting experience. It’s fascinating to see the subtle variations on various themes and character types across the movies, and to see an actor appear as a lead in one film and an extra in another, as Gellar did in “Cruel Intentions” and “She’s All That.” Here, in the order in which they were released, are the teen movies that made 1999 such a memorable year.

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