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In case no one has mentioned these:
The Iceman and the Psychiatrist
and
The Iceman Tapes: Conversations with a Killer
These are 2 documentaries about Richard Kuklinski, who worked as a contract killer for the mob for many years. He started killing people in his teenage years and estimates that he has killed over 200 people. There might have been a 3rd one too.
Here's a clip:
http://youtube.com/watch?v=rBSDiCu4Bb8
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The 2 full versions of this are on youtube.
Anyone got links to any documentaries on youtube? Didnt look through the whole thread, but I found the iceman stuff really interesting and would love to watch more.