You don't look that much like him! But his sister is your boss? That's pretty cool. What does she/you do for a living? Probably you've been getting it since 30 Rock started. He wasn't so well known before that, maybe the most high-profile thing he'd done (that I'm aware of) was cameos in Arrested Development.
He's not really goofy and unattractive, that's just his on-stage persona. He's kinda cute, really.