6. American Pie (1999)
In this late '90s classic that epitomized Tara Reid's brief attractiveness and lends hilarity to her subsequent tumble to Hollywood's D-list, four dork pals make a pact to lose their V-cards by prom night.
Pie fucking, "Stiffler's mom," "shitbreak," "band camp," jizz drinking, two exponentially shittier sequels, and four incomparably even shittier DVD spin-offs result. Mena Suvari, Natasha Lyonne, and flute fan Alyson Hannigan also star, along with Shannon Elizabeth who has never been more taut and premature-ejaculate making as an unclothed foreign exchange student with few lines.