I've been re-watching The Mighty Boosh late-a-ly, and this time I think I've got it. I was always uncomfortable with how the Vince character is...perfect. Except for being a little dumb, he's beloved and usually very lucky. How can you have a comedy work with a character like that?
But what makes it work is that this character is best friends with Howard, a rather loser-ish, history-teacher-type, and chooses to spend most of his time with him. It's like if Jenny Lewis were best friends with Andrea Dworkin, and neither of them were successful. Do you get it now, too?
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