5) American Pie
The hottest girl in school is coming over to get your help studying, her grasp of the English language isn’t that great, and for some inexplicable reason she seems to be into you at least half as much as you’re into her. So what do you do? Set up a webcam, excuse yourself from the room while she changes, and then record the titillation for you and your buds. But in American Pie, that’s just the beginning of the story.
Considering that at this part of the film, our hero Jim (Jason Biggs) had already been caught using a freshly-baked apple pie as a sex toy, it should come as no surprise that his attempted seduction of his gorgeous Slovakian classmate Nadia (Shannon Elizabeth) did not go off without a hitch. First of all kids, back in 1999, hooking up a webcam and sending the feed to your friend’s computer required some effort. Skype was still a gleam in some programmer’s eye at that point, and mistakes were plentiful. Secondly, don’t leave your porn magazines lying around when you have a girl coming over. Unless it turns out she’s into it, and starts to, ahem, take matters into her own hands. At this point, luckily for Jim, it’s fish in a barrel time.
Unfortunately for Jim, this being his first time and all, he can’t, um, meet the minimal mechanical requirements. Let’s just say the equipment failed before it ever got a chance to be used in the field. Twice. It’s bad enough that you literally get this close to bedding your high school crush, but for things to go down the way they did… Well, let’s just say that the ’90s teen film Jim should have been a character is Can’t Hardly Wait. Twice. Good thing, then, that the whole experience was broadcast to the entire school via the webcam and the accidental connection sent to every student at East Great Falls High School who got to see that Jim can’t, uh, hold up his end.
The reason the the Biggs/Elizabeth non-tryst in American Pie is one of the funniest cinematic sex scenes is because it’s not technically a sex scene. There’s also a reality to it, because everyone can relate to the fact that the first time doesn’t go as planned. There’s always a collision of expectation and actuality that sometimes results in one or both of the partners getting short-changed. In Jim’s case, it’s just too bad he underestimated his own potency, while Nadia over-estimated it. Twice. By comparison, being used by the band chick, who slapped him in bed and screamed “Say my name, bitch!” was a definite step up.
– Adam Donaldson