Kevin Mitnick and Emmanuel Goldstein are undoubtedly the most widely known names in the black hat community*. In a series of videos from CNET News, they describe and demonstrate social engineering techniques.
On the same subject, this video demonstrating how easy it is to social engineer you way into clubs by pretending you’re the DJ is worth your time.
*I guess Kevin Poulsen should be on that list too… now the senior editor at Wired News and author of Threat Level.