Titus, on FOX
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This ran for 54 episodes over three seasons, but I'm sure I didn't see nearly all of it. I liked the show well enough when I did watch it (though I certainly didn't love it). It was based on the stand-up comedy of Christopher Titus, who basically played himself in the show (his character was also named Christopher Titus). He had a girlfriend named Erin (Cynthia Watros). He had a father named Ken (Stacy Keach), a half-brother named Dave (Zack Ward, no relation, who I'd later see on a couple eps of Dollhouse), and a friend named Tommy. Most if not all of the characters were dysfunctional in any number of ways. Stories were often intercut with black & white scenes of Titus addressing the viewer, to talk about what was going on in the story, or whatever. The subject matter of the series was generally about serious, potentially controversial issues, and like the star's own comedy, often dealt with these issues in a way that was simultaneously funny and serious, even sometimes angry. I'm afraid I don't really remember any specific stories, but... it was definitely a good show, and I'd like to see it again sometime, to refresh my memory.