The most notorious pie scene ever comes in this 1999 teen sex comedy that raised the bar (or lowered it, maybe) for gross-outs and embarrassment for the sake of laughs. Actually, the movie’s overarching joke – and it’s a film that grasped this before most – is that, in the Internet era, there’s no longer any expectation of privacy, so you shouldn’t expect your most shameful sexual secrets to remain secret for long.
This holds true repeatedly for the virginal Jim (Jason Biggs). Told that a woman’s genitals feel like warm apple pie, Jim spies his mom’s freshly-baked pastry cooling in the kitchen and does to the pie what Alexander Portnoy once did to a piece of liver, only to be caught in the act by his dad (Eugene Levy). Hard to tell who should be more embarrassed: Jim? Or Biggs, who will forever be known as the actor who humped a pie?