6. Shannon (Mallrats)
Kevin Smith's sophomore effort may not have opened to a lot of critical or commercial acclaim, but has since gained a cult following in the years since its release. Brodie, played by Jason Lee, has just been dumped by his girlfriend who now appears to be dating the proprietor of the Fashionable Male shop in the mall, Shannon. Shannon, played by Ben Affleck before he made it big, is a scumbag with sexual proclivities that involve preferring sex with women in uncomfortable places... you know, like the back of a Volkswagen. Fortunately for Brodie (and his lady-friend Rene), Shannon is arrested for having sex with a minor, the tape of which is displayed to the entire mall.
Why We Can't Help But Love Him: The fact that there is video evidence of this man attempting dirty talk by using the phrases "Who's your favorite New Kid" and "call me Donnie" solidify this classic Affleck role on this list.