Long before The 40-Year-Old Virgin made films about horny underachievers an acceptable cinematic genre, Kevin Smith was the immature American movie-going male's primary source of highbrow dick jokes. Smith's latest film, Zack and Miri Make a Porno, may seem like a grand experiment of Smith's in X-rated transgression, but an overview of the director's long and delightfully vulgar career shows us that Kevin Smith has been making audiences cringe for as long as he's been making them laugh.

Clerks

Smith's notoriously cheap black-and-white debut may be visually low-key, but the director's pornographic sensibilities were well under way from the moment he yelled his first "action." In the clip below, 14 years before Smith would devote an entire film to the adult entertainment industry, a sex-obsessed video store proprietor named Randall places the most vulgar order of VHS cassettes in home video history: