Animal House (1978)
One of a string of irreverent comedies making fun of status quo America (think Stripes, Meatballs, Caddyshack), this film remains the high-water mark of anti-establishment humor. If you haven't seen this yet, come out from under that rock and get ready to laugh.
Wonder Boys (2000)
A great send-up of relationships between college professors and their students, this adaptation of Michael Chabon's novel pokes holes in the myths that grow up around educators, with plenty of pot smoking and bad behavior along the way, as well as a great soundtrack.
The Rules of Attraction (2002)
Adapted from Bret Easton Ellis's novel of the same name, this dark comedy follows a quintet of brooding and lustful students who attend the fictional Camden College. There's rape, suicide, drug use, fantasy, love letters, and unrequited love. James van der Beek plays the drug dealing Sean, and he pines for Shannyn Sossamon's character, the virgin Lauren Hynde.
Van Wilder (2002)
Growing up sucks, and if you want to stew on a rip-roaring coming-of-age tale, this National Lampoon classic stars Ryan Reynolds as the comedy's protagonist, and focuses on his inability to cope with the concept of life beyond leaving college and his endless dorm-room escapades. The point here? College is a time to cut loose, sure, but we all have to come to grips with real-life bullshit eventually.
The War on Kids (2009)
Public school can be a nightmare. This documentary unfolds many of the reasons why, from comparing schools to prisons (there's even a quiz so you can try to identify which is which) to interviews (with such luminaries as John Taylor Gatto) to prescription pills, illicit drugs, and school violence, WOK is an indie glimpse at the flip side of education. It's stuff you probably intuitively know, but haven't seen quite like this.