American Pie - (1999)

From getting it on with an apple pie, to being humiliated for your lack of stamina on a live web stream, teen comedy 'American Pie' contains many cringe inducing scenes.

Jason Biggs' character, high school senior Jim Levenstein, bares the brunt of these bedroom misadventures before having a prom night to remember with band member Michelle (Alyson Hannigan).