5. Max Payne
Nothing has ever went well in Max's life and it's understandable how he has ended up a borderline alcoholic. Despite all his misfortune though, he still somehow manages to see the cruel irony in the world and just gets on with life, going from job to job while keeping everyone else at bay. You may think that he sounds very depressing to drink with but let's face it- when you drink with him, you can take pleasure in the fact that maybe your life doesn't suck as bad as you thought.