1. Can’t Hardly Wait
Ah, the fateful “last party of high school” tale. Starring Jennifer Love Hewitt, this movie’s message was YOLO long before anyone knew who Drake was. It taught us about social hierarchy, life after high school, the fear of moving on and the realization that the people you grew up with are rapidly changing. Oh, and in a blink-and-you-missed-it moment, you may have caught a young Jason Segal as the stoned Watermelon Guy.
2. 10 Things I Hate About You
Any guy who can pull off the profess-his-love-for-his-girlfriend-on-a-loudspeaker-in-front-of-the-whole-school move might have an 11th reason to hate him. And who could forget a baby-faced Joseph Gordon-Levitt, the shy freshman pinning for the popular girl? Fun fact: both Gordon-Levitt and Ledger starred in Batman films: Ledger in The Dark Knight and Gordon-Levitt in The Dark Knight Rises (out July 20).
3. Cruel Intentions
Who could forget that infamous girl-on-girl kiss that showed us just how conniving Sarah Michelle Gellar can be? Cruel Intentions also brought together bad boy Ryan Phillippe and girl-next-door Reese Witherspoon, who were up against Winona Ryder and Johnny Depp for most amazing 90s couple ever. Speaking of the 90s, hi Sarah Michelle Gellar’s frosted lipstick, so glad you could join us.
From Cher’s closet to the ancient cell phones and the priceless lingo, this movie was the epitome of the 90s. Cher Horowitz may seem like a ditzy blonde from Beverly Hills, but deep down all she really wants is to help others, fall in love, and make her father proud.
5. American Pie
The raunchfest begins with this series, from Michelle’s now famous “this one time at band camp” speech to Jim’s, um, infatuation with apple pie. It spawned a plethora of other movies, the most recent bringing most of the original cast together again for American Reunion this past April. It’s weird to think all the teens are now grown up and starting their own families.
6. Never Been Kissed.
This is one of the movies that inspired me to study journalism. You couldn’t help but root for Josie Grossie the whole time. I mean, her suggestion for a “Millennium Dance”? Y2K was so 12 years ago. Fun fact: Octavia Spencer, the Oscar-winning actress for The Help, plays a fellow journalist in the film.
7. She’s All That
Playing ultimate jock Zack Syler, Freddie Prinze Jr.’s smooth moves could have won any girl’s heart. But after making a bet with his friends, he has to turn resident geek Rachael Leigh Cook into the prom queen. Check out Anna Paquin, aka Sookie Stackhouse of True Blood, as Zack’s little sister Mackenzie.
8. Get Over It
Okay, so it’s not quite a 90s movie, but it’s close enough. Ben Foster just lost the love of his life to some rock jock portrayed by 90s hottie Shane West (with a British accent!), and with the help of his friends, he tries out for the school play to win her back. Co-starring Sisqo (remember the “Thong Song”?) and Kirsten Dunst, this flick channels Shakespeare’s A Midsummer Night’s Dream.
9. Whatever It Takes
This movie put two of the dreamiest boys of the 90s in one great teen classic. Shane West played a sensitive guy who plays the accordion in his spare time (um, okay), while James Franco played (what else?) the popular pretty boy pining for Shane’s neighbor. Swoon.
10. Bring It On
“I’m sexy, I’m cute, I’m popular to boot!” Although not technically a 90s movie, Bring it On made every girl in America want to become a cheerleader (or maybe that was just me). Kirsten Dunst ruled the school as Toros captain Torrence, and put the other sequels (should I even call them that?) to shame.