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.
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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“Varsity Blues”
Image Credit: ©Paramount/Courtesy Everett Collection / Everett Collection Decades before he became the CEO of Paramount, Brian Robbins specialized in directing offbeat sports movies like “Ready to Rumble” and “Hardball,” but this is still the best of the bunch thanks to one of the best ensemble casts in a year that was full of them. One-half “Porky’s” and one-half “Friday Night Lights,” this odd blend of raucous teen sex comedy and earnest coming-of-age film (with a grim bit of “Concussion”-esque cultural commentary thrown in) feels surprisingly unified given its grab bag of elements; somehow Robbins and screenwriter W. Peter Iliff (“Point Break”) manage to deftly transition from beer- and nudity-fueled juvenile pranks to sequences of harsh physical and mental anguish and back again. What makes the movie work is a cast of talented young actors going for broke: James Van Der Beek, Scott Caan, Ali Larter, Amy Smart, and others clearly knew this was their big shot, and they bring everything they’ve got to the movie. Caan and Larter in particular exhibit the kind of “who the hell is that?” screen presence reminiscent of Mickey Rourke in “Body Heat” or Gwyneth Paltrow in “Flesh and Bone,” with each of them bringing nuance and charisma to parts that easily could have been throwaways in lesser hands.
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“She’s All That”
Image Credit: ©Miramax/courtesy Everett / Everett Collection Like most of the films on this list, “She’s All That” boasts a staggeringly impressive cast, with a perfectly balanced combination of already established young actors (Matthew Lillard, Anna Paquin) and talented newcomers (Gabrielle Union, Kieran Culkin, Dulé Hill) supporting the irresistible pairing of leads Freddie Prinze Jr. and Rachel Leigh Cook. This is filmmaking as alchemy — it’s difficult to pinpoint what makes “She’s All That” work so much better than any number of other, similar teen rom-coms given that it’s just as silly and just as predictable, but somehow the intersection of these particular actors with this particular script (by R. Lee Fleming Jr. and an uncredited M. Night Shyamalan) and this particular director (Robert Iscove) at this particular time yielded magic. The cast’s infectious good cheer combines with Iscove’s vibrant palette and energetic camera to create a lively ride that never slows down — even if the story stops dead in its tracks for an unmotivated (but thoroughly enjoyable) musical number choreographed by future directors Adam Shankman and Anne Fletcher. (That musical number is part of an insanely elaborate prom, a trope that one will see in several of 1999’s teen flicks.)
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“Jawbreaker”
Image Credit: ©TriStar Pictures/Courtesy Everett Colle / Everett Collection Darren Stein’s black comedy about a group of mean girls who inadvertently kill one of their own was unfavorably measured against “Heathers” at the time of its release, but the comparison says more about the laziness of the film’s critics than it does about the movie itself. Yes, the two movies share a cynical sensibility and candy-colored palette, but Stein’s effects are slightly less heightened than “Heathers” director Michael Lehmann’s — he skillfully straddles the line between mainstream studio fare and the more outré teen provocations of Gregg Araki, and in the process finds a comic tone all his own. Jammed to the hilt with quotable dialogue and scenery-chewing performances (Rose McGowan channeling Gene Tierney in “Leave Her to Heaven” is a particular joy), “Jawbreaker” is also a master class in merging image and music; while some of the era’s lesser teen movies slather their synthetically assembled soundtracks onto the celluloid like spray paint, Stein’s needle drops are impeccably chosen and perfectly timed to underline and deepen the emotional content of each scene. The girls strolling down the hall post-murder to Imperial Teen’s “Yoo Hoo” remains one of the most iconic images in teen movie history.
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“Cruel Intentions”
Image Credit: ©Columbia Pictures/Courtesy Everett Collection Repurposing classic works of literature in teen films was a popular practice in the late ’90s thanks to the success of Amy Heckerling’s Jane Austen riff “Clueless”; “She’s All That” took elements of its plot from “Pygmalion,” “10 Things I Hate About You” from “The Taming of the Shrew,” and in this smart, sexy, and very funny melodrama, writer-director Roger Kumble expertly mines “Les Liaisons Dangereuses” as source material for a nasty tale of romantic manipulation among the young and rich in New York. The 1999 tradition of killer casts continues here, with Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon playing every emotional and comic beat flawlessly; the film’s aggressive naughtiness could have felt forced, but Kumble and the actors perfectly calibrate the line between pathos and sleaze, making the film both genuinely trashy and genuinely moving. It has the appeal of a guilty pleasure but there’s no need to apologize for it because it’s so impeccably assembled on every conceptual and visual level — it’s as though Douglas Sirk came back from the grave to direct an episode of “Gossip Girl.”
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“The Rage: Carrie 2”
Image Credit: ©United Artists/Courtesy Everett Collection Director Katt Shea’s follow-up to Brian DePalma’s 1976 classic wasn’t particularly well regarded in 1999, and it’s easy to see why; it lacks both the structural precision and emotional complexity of the original film, to which it’s connected in rather flimsy and contrived ways — no coincidence, given that it started life as an original screenplay and was reverse engineered to be marketed as a sequel. Yet if you can put the first film out of your head and accept “The Rage: Carrie 2” on its own terms as a self-contained thriller, it has considerable strengths. Just as she smuggled feminist ideas into exploitation flicks like “Stripped to Kill” and “Dance of the Damned” when she was working for Roger Corman in the late ’80s, here Shea subverts the conventions of the late ’90s teen film to present a confrontational portrayal of toxic masculinity that serves as a kind of answer to the “boys will be boys” misogyny of “Varsity Blues.” The kind of guys who served as identification figures in that film are chilling villains here, as Shea deglamorizes and deconstructs their sexual aggression and, in the process, critiques a whole subgenre of teen movies from “Porky’s” to “American Pie.” “The Rage: Carrie 2” is also a reminder of what a skilled stylist Shea is; she knows how to make every camera movement and cut count, and, as in much of Shea’s work, there’s an elegance here that makes what could have been a standard work for hire a truly expressive and personal film.
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“10 Things I Hate About You”
Image Credit: ©Buena Vista Pictures/courtesy Everet / Everett Collection “10 Things I Hate About You” is probably the most classically satisfying teen movie of 1999, and no wonder — screenwriters Karen McCullah Lutz and Kirsten Smith found their underlying structure in Shakespeare’s “The Taming of the Shrew.” Their script is a smoothly engineered entertainment delivery system, providing laughs and heart in equal measures via characters archetypal enough to be immediately accessible but specific enough to keep the film from blurring together in the memory with the many similar rom-coms released right before and after. Without question, Lutz and Smith’s terrific script got an extra boost of luck when Heath Ledger and Julia Stiles were cast in the lead roles; they play their characters’ arcs from rebellious resistance to romantic resignation so honestly that the movie rarely feels formulaic, even when it’s hitting the most familiar beats imaginable.
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“Never Been Kissed”
Image Credit: ©20thCentFox/Courtesy Everett Collection Drew Barrymore plays not a high school student but a journalist pretending to be a high school student in this comedy that nevertheless qualifies as a teen movie given the high schoolers who surround Barrymore (played by Jessica Alba, Marley Shelton, Jordan Ladd, James Franco, and a pre-“Eyes Wide Shut” Leelee Sobieski), and the clever tweaks to the teen rom-com formula that screenwriters Abby Kohn and Marc Silverstein mine from their premise as Barrymore falls in love with teacher Michael Vartan. To say the movie stretches the limits of one’s suspension of disbelief is an understatement — Barrymore plays her part at such an extreme pitch that she’s not only unconvincing as a teenager, she’s unconvincing as a functioning homo sapien — but as the movie progresses, Barrymore’s unconventional choices take on a life of their own and become weirdly admirable. In its own way, her twitchy, exaggeratedly neurotic performance is the boldest and most original comic turn in a studio movie since Jim Carrey in “Ace Ventura: Pet Detective.”
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“Election”
Image Credit: ©Paramount/Courtesy Everett Collection A high school comedy for MTV Films might seem like an unlikely fit for erudite satirist Alexander Payne, but in Tom Perrotta’s novel about a corrupted student government race, Payne found the ideal framework to comment on American politics at the end of the millennium. Just as Paul Brickman turned the teen sex comedy into a delivery system for a radical dissection of Reagan-era capitalism in “Risky Business” in 1983, Payne found in Tracy Flick a metaphor for feminist ambition and the cultural backlash against it — a backlash ironically encapsulated in many of the commentaries on the film, which cast Reese Witherspoon’s Flick as a soulless shrew reminiscent of a certain First Lady. Viewed today, Flick still works as a Hillary Clinton stand-in, but her anguish as she runs for office against a hopelessly unqualified moron has become more pointed and relatable. Justice for Tracy Flick at last!
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“Idle Hands”
Image Credit: ©Columbia Pictures/Courtesy Everett Collection By 1999, “Scream” had inspired a wave of young adult horror movies that included “I Know What You Did Last Summer,” “Urban Legend,” and “Phantoms,” but there were still a few last gasps to come (culminating in “Urban Legend” director Jamie Blanks’ glorious “Valentine” in 2001). This tale of a stoner (Devon Sawa) whose hand becomes possessed and starts wreaking havoc isn’t exactly original — it’s basically a 90-minute extension of the most famous set piece from Sam Raimi’s “Evil Dead 2” — but what it lacks in freshness it makes up for in gory enthusiasm. The trio of leads (Sawa, Seth Green, and “She’s All That” alumnus Elden Henson) relish in the excess, and director Rodman Flender does a nice job of delivering a few honestly terrifying moments sprinkled throughout what is essentially a modern-day “Three Stooges” comedy. Like Katt Shea, Flender graduated from the Roger Corman school of filmmaking, and like Shea, he knows how to deliver the exploitation movie goods with gusto and panache.
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“American Pie”
Image Credit: ©Universal/courtesy Everett / Everett Collection The “Citizen Kane” of teenagers losing their virginity movies, “American Pie” takes the raw materials of one of the least heralded movements in North American film — the post-“Porky’s” wave of sex comedies that included “Losin’ It,” “Screwballs,” “Joysticks,” and about a hundred others — and resynthesizes them into something smarter, funnier, and more poignant than any of its cinematic ancestors. Which isn’t to say it doesn’t have plenty of bad taste to go around — this is a movie that takes its title from a guy jerking off into a pie, and that’s one of its less offensive scenes — but at the end of the day, the vulgarity dovetails with some surprisingly sensitive characterizations and a generosity of spirit aimed at characters young and old, cool and nerdy, male and female. Most of the actors here were relatively new to the screen, and all of them (the cast includes Jason Biggs, Tara Reid, Seann William Scott, Natasha Lyonne, Alyson Hannigan, Chris Klein, and Mena Suvari) are great — in fact, most of them have never been better. It’s the best kind of Hollywood studio movie, one that delivers all the expected satisfactions of its genre along with a bunch you didn’t see coming.
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“The Wood”
Image Credit: Paramount Two decades before he became known for the sci-fi spectacle of “The Mandalorian” and “Ahsoka,” Rick Famuyiwa directed and co-wrote (with cultural critic and film historian Todd Boyd) this sweet and funny coming-of-age film in which a group of friends reflects on their teen years together on the eve of one’s wedding. The framing story involving the guys as young men is possibly what helped get the movie financed (as adults, they’re played by Taye Diggs, Omar Epps, and Richard T. Jones), but the flashbacks to high school are what really distinguish the film. Drawn from Famuyiwa’s memories of growing up in Inglewood, “The Wood” is the best kind of “slice of life” movie, a film that exhibits observational insight and relatable humor in nearly every scene; its ability to consistently find the dramatic in the ostensibly unremarkable makes it a classic.
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“Drop Dead Gorgeous”
Image Credit: ©New Line Cinema/Courtesy Everett Collection The most savagely mean-spirited movie on this list, “Drop Dead Gorgeous” is as ruthless as “American Pie” is generous — no one in the film, with the arguable exception of beauty pageant contestant Kirsten Dunst, is spared by writer Lona Williams and director Michael Patrick Jann’s mercilessly savage satirical eye. As a young woman, Williams competed in several pageants herself, and evidently she had a few scores to settle with her competitors, their parents, the judges, and everyone else involved with the process; this mockumentary following the participants in a Minnesota “teen princess pageant” ridicules them all, and it does so fearlessly and hilariously. In a film packed with standout comic performances and scenes, Denise Richards stands out as the entitled beauty queen from hell, but there are plenty of great moments to go around for actors like Dunst, Amy Adams, and Brittany Murphy; the condescension the filmmakers display for their characters might not be to everyone’s taste, but if you’re the kind of person who thinks early John Waters films are just a little too kind, this is the movie for you.
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“Dick”
Image Credit: ©Columbia Pictures/Courtesy Everett Collection This one is a true oddity — and a truly wonderful one. Consistently underrated auteur Andrew Fleming (“Bad Dreams,” “Threesome”) and his co-writer Sheryl Longin reimagine the Watergate scandal from the point of view of two teenagers (Kirsten Dunst and Michelle Williams) who stumble into jobs as White House dogwalkers; through a series of increasingly clever and amusing complications, they then stumble further into history, ultimately becoming the “Deep Throat” made famous in “All the President’s Men.” It’s an audacious premise, flawlessly executed by Fleming with retina-scorching ’70s-era production design and a well-curated soundtrack of needle drops that makes this a teen comedy you can almost dance to. Dunst and Williams’ comedic gifts have been on display many times since, but their giddy goofiness here is still a treasure to behold; they’re lovable, ridiculous, and utterly compelling from beginning to end.
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“Teaching Mrs. Tingle”
Image Credit: ©Dimension Films/Courtesy Everett Collection “Scream” scribe Kevin Williamson made his feature film directorial debut with this unusual comic thriller, a teen take on “Misery” in which a trio of teenagers take their awful teacher hostage and keep her tied to a bed for most of the film’s running time. In its toxic relationship between an educator and her students and the themes about ambition and self-definition that bubble up from time to time, the film echoes “Election” in interesting ways, but it’s a softer, less caustic take on the material. Williamson’s “Dawson’s Creek” side is on full display in the mopey musings of its cast in between suspense sequences, and it’s actually what makes “Teaching Mrs. Tingle” so intriguing — it’s like a group therapy session with the threat of murder hanging over every scene. Whether that aspect of the movie would have felt even more pronounced if it had stuck with its original title “Killing Mrs. Tingle” (changed in response to the shootings at Columbine), we’ll never know.
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“American Beauty”
Image Credit: ©DreamWorks/Courtesy Everett Collection “American Beauty” may be narrated by a deceased 42-year-old whose midlife neuroses motivate much of the narrative’s action, but it’s also a teen movie that devotes a great deal of energy and sympathy to the three high schoolers pictured above. Like many of the films released in 1999 and just before (“Rushmore,” “Fight Club,” “Election”), “American Beauty” lives in the shadow cast by Mike Nichols’ “The Graduate”; it’s as clever and conflicted in its study of young people trying to find their bearings in 1999 suburbia as that film was in raising the question of whether or not young Benjamin Braddock would go into “plastics.” The world view of “American Beauty” whipsaws between total cynicism (the only viable plan for the future any of the teenagers has is as a professional drug dealer) and a somewhat unearned romanticism (Wes Bentley’s oft-parodied monologue about the “beauty” he sees in a plastic bag blowing around a parking lot), but there’s a consistent and profound sense of aching disillusionment shared among the three teens that remains haunting 25 years later.
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“Drive Me Crazy”
Image Credit: ©20thCentFox/Courtesy Everett Collection Best known at the time of its release for the tie-in music video starring Britney Spears and best known now as an early starring vehicle for “Entourage” star Adrian Grenier, “Drive Me Crazy” is a lightweight but extremely enjoyable romantic comedy that closes out the 1999 teen cycle with effervescent charm. The script is by Rob Thomas, whose teen bonafides are unassailable: Before this, he wrote an episode of “Dawson’s Creek,” and after it he created the TV series “Veronica Mars” and developed the reboot of “90210.” Thomas has a nice ear for teen dialogue that’s funny without feeling overly clever and romantic without becoming unrealistically poetic; even though the two leads (Grenier and Melissa Joan Hart) are, to put it politely, chemistry-challenged, the movie works thanks to Thomas’ light comic touch and director John Schultz’s brisk sense of pace.
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“The Virgin Suicides”
Image Credit: Paramount This one is a bit of a cheat since “The Virgin Suicides” didn’t open theatrically until the spring of 2000, but it premiered at Cannes in 1999, so let’s include it! After all, it just may be the greatest of all the films on this list, a one-of-a-kind teen movie that’s lyrical, disturbing, funny, and tragic all at once. Writer-director Sofia Coppola appeared in her dad Francis’ movie “Rumble Fish” when she was young, and like that film, “The Virgin Suicides” is a kind of art-house movie for teenagers, a richly atmospheric and mysterious fever dream that reveals new layers of meaning every time one revisits it. Told from the point of view of the boys who are obsessed with but do not understand the sisters at the movie’s center, “The Virgin Suicides” pulls off the amazing narrative hat trick of revealing all the things the boys didn’t know even while telling the story from their perspective. It’s a great movie about what it’s like to be a teenage girl, what it’s like to be a teenage boy, and what remains mysterious about each to the other and to themselves.
