17. Road Trip (2000)
They always say "never make a sex tape." But if you absolutely have to, don't send footage of you with a jumpoff to the girl of your dreams. When Josh Parker (Breckin Meyer) does just that, he and his goons (Seann William Scott, Paulo Costanzo, and DJ Qualls) hit the road to intercept it.
Plenty of memorable fuckery—including a rail-thin white dude making sweet love with a large, luscious, black coed—occurs along the way, so stop pumping the brakes on this one.