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I feel you man. This is one reason I don't like to have very good friends as roommates. My current roommates owe me several hundred dollars in bills, one of them I don't mind being a hard ass to, the other I'm closer with and thus have a harder time demanding money from. But clearly your situation is a lot more serious.
You might give him another week to see if he snaps out of it. Some people don't deal well with losing jobs, and he might just need a little time to deal with the situation himself. But if that doesn't work I'd just sit down with him and tell him what you've told us. Tell him that as a friend you're worried about the way his life is headed and that you suspect he's not too happy about it either. Tell him you're willing to help him out for awhile, but not if it just makes you an enabeler of his slow downward spiral. Try to be as friendly and non-confrontational as possible (no one likes being talked down to) but let him know how you feel.
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