You know how sometimes you see that one of your favorite teen movies from the ’90s or early ’00s is on TV, and you decide to watch it since it’s been a while? And then you’re enjoying all the dated cheesiness and unrealistic depictions of high school life, when suddenly you see a familiar face you weren’t expecting? Maybe a now A-list actor or the star of your favorite TV show? And you do a spit take and go “Wait… she’s in this? He plays that character?”
Hey, celebrities have to get their starts somewhere, and sometimes that involves playing a bit part in a silly rom-com about dating bets. And we’ve got ten classic examples for you right here. If you spend tonight marathoning all of these movies and looking for even bigger stars standing in the background during dance scenes, don’t say I didn’t warn you.
10. Jessica Alba in Never Been Kissed
In what looks to be her second ever movie role, Jessica nailed it as a bitchy mean girl who gets covered in dog food and yells at Drew Barrymore. I’m surprised she avoided being typecast as that exact character for the remainder of her career. Speaking of her career, where did it go?
9. James Franco in Never Been Kissed
And let’s not fail to mention James Franco’s first movie role ever, in the same movie. Look at him perfecting his douchebag impression at such a young age. He must have thought it looked really good on him, because he never took it off.
8. Megan Fox in Holiday in the Sun
You might not remember this Olsen twins movie at all, let alone that Megan Fox was in it, but her first-ever role as a bitchy rich girl should be remembered for all of time. She went on to hone that character type in Confessions of a Teenage Drama Queen. Side note: Remember when chokers were a thing people wore?
7. Justin Long in Crossroads
Aww, look at little Justin trying to have sex with Britney Spears. I’m starting to think it was a rule in these movies for the future star to play either a total dweeb or a bitchy popular kid. There’s really no in between for supporting high school characters. So sad.
6. Jason Segel in Can’t Hardly Wait
Sometimes “total dweeb” can also be “stoner,” I guess. This was Jason’s first movie, and he’s actually credited as “Watermelon Guy.” It’s fun to watch him talk about Velma from Scooby Doo knowing he would later date Linda Cardellini, who played Velma in the Scooby Doo movies. Spooky.
5. Kerry Washington in Save the Last Dance
Kerry actually had a pretty big part in this movie, but unless you’re a big fan you might not remember it was her. And now she’s got a baby and a big TV show. Wow, time flies.
4. Aaron Paul in Whatever It Takes
Another dweeb example. You probably only remember Shane West and continuing douchebag James Franco if you remember this movie at all, and yet there’s little Aaron as the kooky best friend.
3. Ashley Benson in 13 Going on 30
See that girl behind Tom-Tom in the group of six chicks? That’s tiny Ashley Benson, better known for her roles on Pretty Little Liars and in weird videos with James Franco. (Wow I’ve mentioned James a lot in this post. Maybe I’m cursed.) And bonus! That girl on the far right is Brie Larson!
2. Josh Radnor in Not Another Teen Movie
I had no idea Josh Radnor was a thing until How I Met Your Mother, and even when that premiered I was still like, “Wait, is that Jimmy Fallon?” But before that he appeared in bit parts on TV shows and in movies like this one, as a tour guide.
1. Usher in She’s All That
After his amazing turn in the fabulous, watch-it-now-or-regret-it-forever teen alien movie The Faculty, Usher played “Campus DJ” in this ’90s classic. That’s his role. Campus DJ. Which is apparently a thing. And he somehow teaches a bunch of slacker high school students a choreographed dance. Yeah…