The Most Underrated Teen Comedies of the 1990s, Ranked
The '90s were the ultimate era for teen comedies being the ultimate form of cinematic escape.
Forget "Clueless" and "10 Things I Hate About You" for a sec, though. Here are some of the lesser-known movies that deserve way more credit than they've gotten.
10. "Can't Hardly Wait" (1998)
This one's the ultimate high school graduation party movie.
Preston Meyers has been crushing on Amanda Beckett for four solid years. Amanda's just broken up with her jock boyfriend Mike Dexter, so Preston sees this as his big chance. He writes her a letter, spills his guts, and the whole movie is about whether or not he can actually give it to her. Remember, this was before texting.
Meanwhile, we've got wannabe-rapper Kenny Fisher trying to lose his virginity and the geeky William plotting revenge on Mike.
9. "Dick" (1999)
Kirsten Dunst and Michelle Williams star as Betsy and Arlene, two ditzy teens who accidentally get embroiled in the Watergate scandal. No, seriously. They start as White House dog walkers and somehow end up becoming President Nixon's secret advisors, nicknamed "The Official White House Dog Walkers." They're the ones who unknowingly suggest the infamous 18-minute tape gap as a "teeny-weeny mistake."
8. "Encino Man" (1992)
High school losers Dave and Stoney dig up a frozen caveman while trying to build a pool in Dave's backyard. They thaw him out, name him Link, and decide to pass him off as a foreign exchange student. As you can guess, the plan works a little too well.
Link becomes the most popular guy in school, and Dave hopes this newfound popularity will help him win over his crush, Robyn. The twist? Robyn starts falling for Link.
7. "Idle Hands" (1999)
Meet Anton. He's so lazy that his hand becomes possessed by a murderous spirit. After accidentally killing his parents, he seeks the help of his equally clueless friends, Mick and Pnub. They try to stop the hand by any means, including, get this, severing it. The hand goes on a killing spree, and it's targeting the girl next door Anton has a crush on.
Yeah, it's as wild as it sounds, mixing stoner comedy with horror elements.
6. "She's All That" (1999)
Before extreme makeovers became a TikTok trend, there was Laney Boggs. She's the artsy, glasses-wearing, definitely-not-popular girl in high school. Enter Zack Siler, a jock who bets he can turn any girl into the prom queen. His friends pick Laney, and so begins the transformation—both physically and emotionally. Zack teaches Laney how to be popular while Laney shows Zack there's more to life than popularity.
All this culminates in the classic '90s prom scene, complete with a dance-off.
5. "Drop Dead Gorgeous" (1999)
What's more American than a small-town beauty pageant? This mockumentary style comedy dives into the cutthroat world of teen beauty queens in Mount Rose, Minnesota. Kirsten Dunst plays Amber, a hopeful but poor contestant, pitted against the wealthy and manipulative Becky, played by Denise Richards.
Contestants start meeting bizarre and fatal accidents, but the show must go on, right?
4. "Never Been Kissed" (1999)
Drew Barrymore plays Josie, a 25-year-old journalist who goes undercover as a high school student to research teen culture. The catch? She was a total nerd in high school and never had her first kiss. As she navigates cliques, gets a makeover from her "cool" brother, and falls for her English teacher, Josie finally gets to redo her teenage years.
3. "Slums of Beverly Hills" (1998)
This movie follows the travails of the Abramowitz family, led by their single dad Murray, as they skirt along the fringes of Beverly Hills, moving from one low-rent apartment to another just to stay in the coveted school district. Vivian, played by Natasha Lyonne, is a teen going through puberty and all the awkwardness that entails. She gets a crash course in the birds and the bees when her cousin Rita, a dropout with a drug problem, moves in.
2. "Drive Me Crazy" (1999)
Melissa Joan Hart plays Nicole, a popular girl looking to make her ex jealous by making over her grungy neighbor, Chase, into a prom-worthy catch. Chase agrees because he wants to win back his own rebellious ex. Classic plot, right? But as they each get a peek into each other's worlds, genuine feelings develop.
1. "Jawbreaker" (1999)
This dark comedy is like "Heathers" for the '90s. The "Flawless Four" rule their high school until a birthday prank goes wrong and they accidentally kill their friend with a jawbreaker. Yeah, you heard me right. The queen bee Courtney frames it as a sexual assault and murder, leading to a whirlwind of drama, betrayal, and alliances.