Mark Ratner from "Fast Times at Ridgemont High"
Mark "Rat" Ratner had kind of a weird nickname. His best buddy who couldn't manage to give Jennifer Jason Leigh a ride to the abortion clinic after knocking her up and scalped tickets to kids in middle school seemed like more of a rat. Mark was actually a pretty nice guy, and by the end of the movie he manages to get the girl. The epilogue reveals they still haven't "gone all the way," but I'd like to think he managed to consummate things somewhere during Clinton's first term.
Andy Stitzer from "The 40 Year Old Virgin"
Andy continues the trend of nice guys in movies who can't seem to give it away. He waxes his hairy chest and even parts with his (editor's note: extremely impressive) collection of action figures in an attempt to have sex. It almost makes you wonder how he managed to stay a virgin so long until you remember he has a really hairy chest and an extremely impressive collection of action figures. Those things take focus and dedication, and don't leave a lot of time for ladies.
The Fat Kid from "Stand By Me"
It's safe to say this kid wasn't just a virgin in the film, but most likely in real life as well. Does anyone know what ever happened to him? Let's hope he found some half decent looking girl. He probably thought being a child star would mean marrying a supermodel. Poor little naive bastard.
Jim Levenstein from "American Pie"
Just as a generation of High School students were learning about webcams and the Internet, Jim came along and taught everyone a very valuable lesson: if you try to lose your virginity on camera, bad things are going to happen. Things like premature ejaculation broadcast to your entire High School. Thanks for taking that one for the team, Jim. A lot of us dodged a bullet because of you.
Matt from "The Virginity Hit"
Well, some of us dodged a bullet. I guess Matt never saw "American Pie" because he and his friends seemed to think documenting virginity loss would be smart. I won't spoil this for you since this movie just came out, but suffice to say adding cameras to the equation is never a good idea. It's a funny idea, and it's certainly entertaining for the audience, but it didn't do Matt any favors. All teens should watch this cautionary tale to make sure their most embarrassing moment doesn't wind up on YouTube.
Lewis Skolnick from "Revenge of the Nerds"
Lewis doesn't just lose his virginity to the ultra hot cheerleader, scoring big time for nerds everywhere, he does it while wearing a Darth Vader costume. In a moon bounce. Way to go, Lewis.
The Kids from "Superbad"
Evan, Seth and Fogell. These guys really show the lengths boys in High School will go to in order to lose their virginity. Fake ID's, stealing alcohol from strangers, running from the cops and so much more. They're like the 3 musketeers of teenagers trying to get laid in the new millennium. Also, they advocate safe sex and know better than to take advantage of a girl who's too drunk. And they're hilarious. What's not to love?