Remembering the Best Teen Comedies of the 90s and 00s

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20th Century Fox/Miramax/Buena Vista

Everyone remembers the Golden Age of teen comedies -- the John Hughes era that introduced audiences to a more honest, touching (and touchy-feely), and totally hilarious teenage perspective. Then came 'Clueless,' Amy Heckerling's brilliant 1995 film, which ushered in the Second Coming of teen comedies, paving the way for far more modern and sometimes satirical views on young adult life, love, and angst ... now with the occasional dance number or super cool band cameo.

The late 90s and early 00s gave us some of the best teen comedies ever, and it's a shame because they just don't make 'em like they used to. Actually, they're hardly making them at all anymore. So put on those old flared jeans and join us as we take a look back at the best teen comedies of not-so-long-ago.

  • 'Can't Hardly Wait'

    1998's 'Can't Hardly Wait' is a total teen movie party city. The cast is insanely packed with faves: Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo (aka Peter's son from 'Hook'), Peter Facinelli, Lauren Ambrose, and way, way more. Seth Green thinks he's like, some cool hip-hop dude, which is worth the price of admission alone. There's also PILES of cameos, including Melissa Joan Hart, Jason Segel, Clea DuVall, and Jenna Elfman. Basically, we could spend the entire time just talking about all the people in this movie because that's how awesome this cast is. But it's also a genuinely hilarious film about getting to that point at the end of high school where you're just, like, so over it, and you realize that everyone has been acting way cooler than they are -- and that makes everyone and everything seem pretty dumb. It's also got some super cute little love story elements to it and one of the best worst insults in movie history: "Denise Fleming is a tampon!"

  • '10 Things I Hate About You'

    '10 Things I Hate About You' put a modern (well, for 1999) spin on William Shakespeare's 'The Taming of the Shrew,' complete with all the tiny backpacks and chunky boots that required. Joseph Gordon-Levitt, Julia Stiles, Larisa Oleynik (Alex Mack!) and the late Heath Ledger starred in the complicated love/hate story that teaches us lessons about being honest with ourselves and with others, and not living our lives according to social expectations. Plus it's got a great supporting cast, including David Krumholtz and future cult leader Andrew Keegan, and an amazing soundtrack -- as an added bonus, Letters to Cleo and Save Ferris (look them up, youths) pop up to perform in the film, earning the movie a little extra credit. And who doesn't still have Kat's poem for Patrick memorized (and still know exactly when to start crying)?

  • 'She's All That'

    There was a time in the 90s when Rachael Leigh Cook was totally all that. And 1999's 'She's All That' proves it. Cook plays the dorky girl who just needs to lose the glasses to become a popular hottie (yeah, yeah) so Freddie Prinze Jr. can win a bet and get revenge on his sexy ex-girlfriend or something. Anna Paquin plays his sister, Kieran Culkin play's Cook's hilarious little bro, and Matthew Lillard (yeah, remember this time in our lives?!) plays a 'Real World' house reject. There's also a mega awesome dance number that defies logic -- how many hours did the student body spend learning this routine? Did they hire a professional choreographer? Does it really matter? What matters is that this movie is really funny and very sweet, even if it's a bit silly.

  • 'Josie and the Pussycats'

    'Josie and the Pussycats' came from the writing/directing team that brought you 'Can't Hardly Wait,' so you knew it was going to be something special. While on the surface it seemed like it could be just another cheap attempt to mine vague nostalgia for big box office bucks, 'Josie' was anything but. It's actually a total satire of those kinds of movies, taking digs at consumerist culture with the help of some really catchy songs courtesy of Kay Hanley of Letters to Cleo fame, who provided Josie's singing voice. And this trio is superb: Rachael Leigh Cook, Rosario Dawson, and Tara Reid (who is actually really funny in this -- really). Plus there's Alan Cumming and Parker Posey as hilariously evil executives, and the best fake boy band: Du Jour. Just try to get "Backdoor Lover" out of your head. You cannot.

  • 'Never Been Kissed'

    1999's 'Never Been Kissed' combines the best of teen comedy from the 80s and the 90s with Drew Barrymore playing a homely journalist named Josie (it's all connected!) forced to relive the nightmare of her teenage experience when she's assigned to go undercover at the local high school -- not that anyone would buy Barrymore as a high school kid, but we did all live through 'Dawson's Creek.' Barrymore is forced to snuggle up to the cool kids like Jessica Alba and James Franco, but takes a liking to fellow nerds and falls for her hottie teacher, played by Michael Vartan. The catch is, of course, that Josie (formerly Josie Grossie) has never been kissed, and along the way she learns and helps others learn valuable lessons about not judging other people based on their appearances, and that hey, being smart is way cooler than just looking cool.

  • 'Bring It On'

    Way before Peyton Reed took the gig directing 'Ant-Man,' he directed this hilarious little movie in 2000 called 'Bring It On.' Like, totally, for sure -- maybe you've heard of it? Kirsten Dunst becomes head cheerleader and the newest member of her squad (Eliza Dushku, professional tough girl) clues her in to her former captain's cheer-plagiarism. If you love dance routines, charming satire of high school politics, and fierce insults, this is the movie for you. It's a film about growing up, accepting responsibility, and finding your own voice instead of just being a lame follower. It's also the movie that gave us a major crush on Jesse Bradford. Swoon.

  • 'Drop Dead Gorgeous'

    Another Kirsten Dunst movie?! Yes! But 1999's 'Drop Dead Gorgeous' is an oft-overlooked teen comedy that doesn't really get talked about enough alongside some of these classics. Directed by 'The State' and 'Reno 911!' veteran Michael Patrick Jann, 'Drop Dead Gorgeous' is a faux documentary that follows a group of girls as they vie for the crown in a small town Minnesota beauty pageant. Featuring the likes of Dunst, Denise Richards, Kirstie Alley, Amy Adams, Allison Janney, and the late, great Brittany Murphy, 'Drop Dead Gorgeous' is a fierce dark comedy that pokes fun at everything from teen sex to eating disorders and the beauty industry. It also has murder!

  • 'Jawbreaker'

    1999 gave us another dark teen comedy: 'Jawbreaker,' starring then up-and-comer Rose McGowan as the Queen Bee of the popular girls at school, who are scrambling to hide the accidental murder of their BFF -- which they don't seem that upset about, actually. Also starring former Noxzema spokesmodel Rebecca Gayheart (now that's a deep cut) and Julie Benz, things get messy when the ladies are discovered by one of the nerdy girls, played by a then-little-known Judy Greer. 'Jawbreaker' is basically 'Mean Girls' before 'Mean Girls' but without all the moralizing and the hugging at the end. It's a seriously twisted movie about some seriously messed up high school girls, with a bonus cameo by McGowan's then-fiance Marilyn Manson and a supporting turn from eternal badass Pam Grier.

  • 'Election'

    Alexander Payne's 1999 film 'Election' gave us a very different and totally nutso side of Reese Witherspoon as persistent over-achiever Tracy Flick, who drives high school teacher Jim McAllister (Matthew Broderick, former teen comedy icon) to the brink of insanity with her constant brown-nosing and her plotting to become class president. Based on the novel by Tom Perotta, the film gives us a peek at a more obsessive and candid look at high school life -- albeit one that's way more dismal in comparison to the upbeat teen comedies of the time, but no less hilarious. The film offers this absurd concept of a battle between this grown, adult man and this relentlessly cheerful teenage girl, and it gives us probably the only actually good Chris Klein performance in recorded history.

  • 'Not Another Teen Movie'

    This is the teen comedy to end all teen comedies. When 'American Pie' and slasher movies arrived on the scene, they kind of killed this era of teen comedies, as films for teens started relying heavily on crude humor and searching for the next horror gimmick to launch a franchise. So 'Not Another Teen Movie' is like our swan song, lovingly satirizing all of our favorite teen movies, including almost all of films on this list. It's the film that kickstarted the career of Chris Evans, who plays the role of generic jock/popular guy, who makes a bet to turn the nerdy girl into a super sexy popular girl by prom night, but along the way there's all the other elements from other teen movies of the time, like cheerleading politics, the big football game, the school dance confrontation, and chasing the girl down at the last minute to apologize. Unlike the other dumb spoof movies that followed, 'Not Another Teen Movie' is actually funny -- it didn't just make pop culture references that wouldn't be relevant by the time it hit DVD, and it worked just as hard to make us laugh as the teen movies it was satirizing. It knew why we loved those movies, but also what was so silly about them. A real satire has respect for its subject, and 'Not Another Teen Movie' embraces the genre, laughing with it, not just mercilessly ridiculing it. To lend it some extra cool cred, it has cameos from Melissa Joan Hart, who starred in 'Drive Me Crazy' and 'Can't Hardly Wait,' Sean Patrick Thomas of 'Save the Last Dance,' and 80s icon and John Hughes muse Molly Ringwald.

  • 'Can't Hardly Wait'

    1998's 'Can't Hardly Wait' is a total teen movie party city. The cast is insanely packed with faves: Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo (aka Peter's son from 'Hook'), Peter Facinelli, Lauren Ambrose, and way, way more. Seth Green thinks he's like, some cool hip-hop dude, which is worth the price of admission alone. There's also PILES of cameos, including Melissa Joan Hart, Jason Segel, Clea DuVall, and Jenna Elfman. Basically, we could spend the entire time just talking about all the people in this movie because that's how awesome this cast is. But it's also a genuinely hilarious film about getting to that point at the end of high school where you're just, like, so over it, and you realize that everyone has been acting way cooler than they are -- and that makes everyone and everything seem pretty dumb. It's also got some super cute little love story elements to it and one of the best worst insults in movie history: "Denise Fleming is a tampon!"

  • '10 Things I Hate About You'

    '10 Things I Hate About You' put a modern (well, for 1999) spin on William Shakespeare's 'The Taming of the Shrew,' complete with all the tiny backpacks and chunky boots that required. Joseph Gordon-Levitt, Julia Stiles, Larisa Oleynik (Alex Mack!) and the late Heath Ledger starred in the complicated love/hate story that teaches us lessons about being honest with ourselves and with others, and not living our lives according to social expectations. Plus it's got a great supporting cast, including David Krumholtz and future cult leader Andrew Keegan, and an amazing soundtrack -- as an added bonus, Letters to Cleo and Save Ferris (look them up, youths) pop up to perform in the film, earning the movie a little extra credit. And who doesn't still have Kat's poem for Patrick memorized (and still know exactly when to start crying)?

  • 'She's All That'

    There was a time in the 90s when Rachael Leigh Cook was totally all that. And 1999's 'She's All That' proves it. Cook plays the dorky girl who just needs to lose the glasses to become a popular hottie (yeah, yeah) so Freddie Prinze Jr. can win a bet and get revenge on his sexy ex-girlfriend or something. Anna Paquin plays his sister, Kieran Culkin play's Cook's hilarious little bro, and Matthew Lillard (yeah, remember this time in our lives?!) plays a 'Real World' house reject. There's also a mega awesome dance number that defies logic -- how many hours did the student body spend learning this routine? Did they hire a professional choreographer? Does it really matter? What matters is that this movie is really funny and very sweet, even if it's a bit silly.

  • 'Josie and the Pussycats'

    'Josie and the Pussycats' came from the writing/directing team that brought you 'Can't Hardly Wait,' so you knew it was going to be something special. While on the surface it seemed like it could be just another cheap attempt to mine vague nostalgia for big box office bucks, 'Josie' was anything but. It's actually a total satire of those kinds of movies, taking digs at consumerist culture with the help of some really catchy songs courtesy of Kay Hanley of Letters to Cleo fame, who provided Josie's singing voice. And this trio is superb: Rachael Leigh Cook, Rosario Dawson, and Tara Reid (who is actually really funny in this -- really). Plus there's Alan Cumming and Parker Posey as hilariously evil executives, and the best fake boy band: Du Jour. Just try to get "Backdoor Lover" out of your head. You cannot.

  • 'Never Been Kissed'

    1999's 'Never Been Kissed' combines the best of teen comedy from the 80s and the 90s with Drew Barrymore playing a homely journalist named Josie (it's all connected!) forced to relive the nightmare of her teenage experience when she's assigned to go undercover at the local high school -- not that anyone would buy Barrymore as a high school kid, but we did all live through 'Dawson's Creek.' Barrymore is forced to snuggle up to the cool kids like Jessica Alba and James Franco, but takes a liking to fellow nerds and falls for her hottie teacher, played by Michael Vartan. The catch is, of course, that Josie (formerly Josie Grossie) has never been kissed, and along the way she learns and helps others learn valuable lessons about not judging other people based on their appearances, and that hey, being smart is way cooler than just looking cool.

  • 'Bring It On'

    Way before Peyton Reed took the gig directing 'Ant-Man,' he directed this hilarious little movie in 2000 called 'Bring It On.' Like, totally, for sure -- maybe you've heard of it? Kirsten Dunst becomes head cheerleader and the newest member of her squad (Eliza Dushku, professional tough girl) clues her in to her former captain's cheer-plagiarism. If you love dance routines, charming satire of high school politics, and fierce insults, this is the movie for you. It's a film about growing up, accepting responsibility, and finding your own voice instead of just being a lame follower. It's also the movie that gave us a major crush on Jesse Bradford. Swoon.

  • 'Drop Dead Gorgeous'

    Another Kirsten Dunst movie?! Yes! But 1999's 'Drop Dead Gorgeous' is an oft-overlooked teen comedy that doesn't really get talked about enough alongside some of these classics. Directed by 'The State' and 'Reno 911!' veteran Michael Patrick Jann, 'Drop Dead Gorgeous' is a faux documentary that follows a group of girls as they vie for the crown in a small town Minnesota beauty pageant. Featuring the likes of Dunst, Denise Richards, Kirstie Alley, Amy Adams, Allison Janney, and the late, great Brittany Murphy, 'Drop Dead Gorgeous' is a fierce dark comedy that pokes fun at everything from teen sex to eating disorders and the beauty industry. It also has murder!

  • 'Jawbreaker'

    1999 gave us another dark teen comedy: 'Jawbreaker,' starring then up-and-comer Rose McGowan as the Queen Bee of the popular girls at school, who are scrambling to hide the accidental murder of their BFF -- which they don't seem that upset about, actually. Also starring former Noxzema spokesmodel Rebecca Gayheart (now that's a deep cut) and Julie Benz, things get messy when the ladies are discovered by one of the nerdy girls, played by a then-little-known Judy Greer. 'Jawbreaker' is basically 'Mean Girls' before 'Mean Girls' but without all the moralizing and the hugging at the end. It's a seriously twisted movie about some seriously messed up high school girls, with a bonus cameo by McGowan's then-fiance Marilyn Manson and a supporting turn from eternal badass Pam Grier.

  • 'Election'

    Alexander Payne's 1999 film 'Election' gave us a very different and totally nutso side of Reese Witherspoon as persistent over-achiever Tracy Flick, who drives high school teacher Jim McAllister (Matthew Broderick, former teen comedy icon) to the brink of insanity with her constant brown-nosing and her plotting to become class president. Based on the novel by Tom Perotta, the film gives us a peek at a more obsessive and candid look at high school life -- albeit one that's way more dismal in comparison to the upbeat teen comedies of the time, but no less hilarious. The film offers this absurd concept of a battle between this grown, adult man and this relentlessly cheerful teenage girl, and it gives us probably the only actually good Chris Klein performance in recorded history.

  • 'Not Another Teen Movie'

    This is the teen comedy to end all teen comedies. When 'American Pie' and slasher movies arrived on the scene, they kind of killed this era of teen comedies, as films for teens started relying heavily on crude humor and searching for the next horror gimmick to launch a franchise. So 'Not Another Teen Movie' is like our swan song, lovingly satirizing all of our favorite teen movies, including almost all of films on this list. It's the film that kickstarted the career of Chris Evans, who plays the role of generic jock/popular guy, who makes a bet to turn the nerdy girl into a super sexy popular girl by prom night, but along the way there's all the other elements from other teen movies of the time, like cheerleading politics, the big football game, the school dance confrontation, and chasing the girl down at the last minute to apologize. Unlike the other dumb spoof movies that followed, 'Not Another Teen Movie' is actually funny -- it didn't just make pop culture references that wouldn't be relevant by the time it hit DVD, and it worked just as hard to make us laugh as the teen movies it was satirizing. It knew why we loved those movies, but also what was so silly about them. A real satire has respect for its subject, and 'Not Another Teen Movie' embraces the genre, laughing with it, not just mercilessly ridiculing it. To lend it some extra cool cred, it has cameos from Melissa Joan Hart, who starred in 'Drive Me Crazy' and 'Can't Hardly Wait,' Sean Patrick Thomas of 'Save the Last Dance,' and 80s icon and John Hughes muse Molly Ringwald.

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