How about a more narrow focus. I was thinking about good drug movies to recommend to a friend. Not well-known recent stuff like Trainspotting or Blow, but lesser known dope flicks. I'll start off.

Panic in Needle Park
Cisco Pike
Puppet on a Chain
Salton Sea
Rush
Spun
Drugstore Cowboy (most mainstream of the list)
The Man With The Golden Arm
Bad Lieutenant
Withnail and I
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I really wanted to go to that Bukake because I thought for sure that you were going to be on the receiving end. - Ryan Knox to Jeff Steward