One of my favorites is the
Iceman Richard Kuklinski. They did 2 interviews with him, about 10 years apart, from the prison that he is in and made a film for each one. He was hit man for the mob and admits to killing many people (exact #'s escape me). The person interviewing him is some kind of shrink and throughout the piece they cut in and out of the interview, some reenactments, and actual pictures of the crime scenes. This documentary was very compelling and I've watched it several times. If you like the mafia type stuff, you should really check these out. They are on HBO on demand every once in a while.