The late 90s and early 2000s were a golden era for teen comedies. These films were light-hearted, relatable, and often featured a cast of up-and-coming actors who would go on to become Hollywood stars. Whether you’re looking for a nostalgic trip down memory lane or simply want to introduce your friends to some classic teen comedies, here are nine films worth watching over the weekend. By the way, you can also go to an open-air cinema with friends (read about Open-Air Cinemas in Singapore: A Unique Movie-Watching Experience).
1. American Pie (1999)
“American Pie” is a classic teen comedy that follows a group of high school seniors who make a pact to lose their virginity before graduation. The film features a hilarious cast, including Jason Biggs, Chris Klein, and Alyson Hannigan, and is packed with iconic moments that will have you laughing out loud.
2. Clueless (1995)
“Clueless” is a coming-of-age comedy that follows the life of wealthy teenager Cher Horowitz, played by Alicia Silverstone. The film is a modern adaptation of Jane Austen’s “Emma” and features a fantastic cast, including Paul Rudd and Brittany Murphy.
3. 10 Things I Hate About You (1999)
“10 Things I Hate About You” is a romantic comedy that follows the story of high school student Kat Stratford, played by Julia Stiles, and her love interest, Patrick Verona, played by Heath Ledger. The film is a modern adaptation of William Shakespeare’s “The Taming of the Shrew” and features a fantastic cast, including Joseph Gordon-Levitt and Larisa Oleynik.
4. Bring It On (2000)
“Bring It On” is a comedy that follows the story of a high school cheerleading squad and their quest to win the national championship. The film features a talented cast, including Kirsten Dunst, Eliza Dushku, and Jesse Bradford, and is packed with high-energy dance routines and hilarious moments.
5. She’s All That (1999)
“She’s All That” is a romantic comedy that follows the story of popular high school jock Zack Siler, played by Freddie Prinze Jr., and his bet to turn the nerdy and unassuming Laney Boggs, played by Rachael Leigh Cook, into a prom queen. The film features a talented cast and is packed with memorable moments that will have you laughing out loud.
6. Mean Girls (2004)
“Mean Girls” is a comedy that follows the life of high school student Cady Heron, played by Lindsay Lohan, and her attempt to navigate the complicated social hierarchy of her new school. The film features a hilarious cast, including Rachel McAdams and Tina Fey, and is packed with memorable one-liners and iconic moments.
7. Legally Blonde (2001)
“Legally Blonde” is a comedy that follows the life of sorority girl Elle Woods, played by Reese Witherspoon, and her journey to law school. The film features a talented cast, including Luke Wilson and Selma Blair, and is packed with hilarious moments and iconic fashion.
8. The Princess Diaries (2001)
“The Princess Diaries” is a comedy that follows the life of awkward teenager Mia Thermopolis, played by Anne Hathaway, and her discovery that she is actually a princess. The film features a talented cast, including Julie Andrews and Hector Elizondo, and is packed with memorable moments and heartwarming messages.
9. Can’t Hardly Wait (1998)
“Can’t Hardly Wait” is a comedy that follows the story of high school student Preston Meyers, played by Ethan Embry, and his attempt to win the heart of his longtime crush, Amanda Beckett, played by Jennifer Love Hewitt. The film features a talented cast and is packed with hilarious
