The Union: The Business Behind Getting High, 2004 (not ideally recent)
420 Hour Stand Up, 2009 (it's not a documentary but it's enjoyable)
American Meth, 2007 (documentary-ish)
Facing the Habit, 2007 (eye opening)
American Drug War: The Last White Hope, 2007
DMT: The Spirit Molecule, 2010
Meth, 2006
Super High Me by Doug Benson is too easy. I'm sure you've seen that.
How Weed Won The West, 2010
Methadonia, 2005
High: The True Tale of American Marijuana, 2008
I saved this one for last.
A Huey P. Newton Story, 2001.
A one man play reconstructing Huey P. Newton's situation but tweaking the time slightly forward.
Huey P. Newton was one man in a team of people at the top levels of the Black Panther Party.
I have watched it 7 times. Second time with the captions on so I could get at the marrow of what he was talking about.
And a lot of what he was talking about was drugs.
imho, it was five star entertainment.