The 1995 hit “Clueless” starring Alicia Silverstone and Paul Rudd may have been the quintessential ’90s teen flick. From Cher’s killer wardrobe to the catchphrases and cliques, this slice of life as a privileged teen growing up in Beverly Hills will hold any ’90s girl’s attention span when it plays on TV.
“10 Things I Hate About You”
This 1999 modernization of Shakespeare’s “Taming of the Shrew” became a classic for teens in the late ’90s. There was a character for every teen to identify with, from Julia Stiles’ ill-tempered outcast Kat to Larisa Oleynik’s popular, beautiful Bianca and Joseph Gordon Levitt’s too-nice-for-his-own-good Cameron. Filled with memorable moments like when Heath Ledger’s bad boy Patrick woos Kat by singing “Can’t Take My Eyes Off of You” backed up by the high school marching band and Kat’s poem, this movie has you rooting for all the unlikely love connections.
“Drive Me Crazy”
Starring ’90s teen queen Melissa Joan Hart and Adrian Grenier, 1999’s teen romantic comedy “Drive Me Crazy” was the ultimate story of two childhood friends reconnecting as completely opposite teens. When the two neighbors decide to fake-date each other to make their crushes jealous, romance sparks and leaves crowds of teen girls hoping popular and perky Nicole will in fact fall for activist Chase. Not only did this movie pull at the heartstrings with its teen songs, but it was also a vehicle for Britney Spears’ late ’90s hit of the same name.
This 1994 dramedy starring Winona Ryder, Ben Stiller, and Ethan Hawke follows the challenges of the lifestyle of a typical Gen X-er. Ryder plays filmmaker Lelaina, who is in the midst of making a documentary about the marginalized lives of her friends. She falls for coffee house guitarist Troy, though she ends up dating cable executive Michael, whom she uses to get her documentary on the air. The movie aptly represents the generation of early 20-somethings that came of age with this movie and resonates with them today.
“Dazed and Confused”
The 1993 coming-of-age comedy “Dazed and Confused” did more than serve as a breakout vehicle for stars from Matthew McConaughey and Ben Affleck to Milla Jovovich. This movie, centering on the last day of senior year and the hazing of incoming freshmen, connected so much with ’90s kids that it developed a cult following and was named one of the top 10 movies of all time by renowned director Quentin Tarantino.
“She’s All That”
Starring Freddie Prinze, Jr., as popular jock Zack and Rachael Leigh Cook as nerdy Laney, the 1999 flick “She’s All That” was one of the most popular teen movies of the ’90s. After Zack’s popular girlfriend dumps him shortly before prom, he bets his friend that he can turn any girl into prom queen, even unpopular and dorky Laney Boggs. Zack takes an interest in Laney by ridding her of her glasses, ponytail, and paint-splattered overalls and transforms her into a popular girl and finds true love. This movie gave every less-than-popular girl hope that a good looking guy would transform her into a queen bee but fall in love with the real her at the same time.
This 1997 smash hit starring Kate Winslet as down-on-her-luck society girl Rose and Leonardo DiCaprio as free-spirited starving artist Jack won the hearts of every girl growing up in the ’90s, while still offering enough epic adventure to entertain the guys as well. The film topped the box office and had fans lined up for hours for a chance to see the epic romance and swoon over DiCaprio’s good looks.
This 1994 epic dramedy starring Tom Hanks, Gary Sinese, Sally Fields, and Robin Wright centers on the adventures of the slow-witted yet golden-hearted Forrest Gump as he unexpectedly finds himself in the midst of defining moments in history. The movie made countless kids shout “Run, Forrest, run!” during gym class and others spout the wisdom that “Life is like a box of chocolates. You never know what you’re gonna get.”