American Pie (1999)

Rowdy coming of age sex comedy directed by Paul Weitz.

Four high-school boys are reaching that age where only one thing is on the mind: sex for the first time. When the friends challenge one another to do it before senior prom, they variously join a choir, help a student with school work and even hang out with geeks in the pursuit of what they believe is the ultimate status-gaining act. But when it comes down to it, going the whole way is more frightening than they realized.