I would have to say the first celeb that comes to mind for me is Howie Mandel. I think the transformation in him was among the most extreme I've seen in celebs going bald. Going from that giant mop top to bald and earrings is a bold statement. I seen him right after he shaved it and thought, wow that is a good look right there, really fits him. I shaved not long after...but was on the edge anyway. I wouldn't say he pushed me over the edge, but I'd say I liked the way he looked and thought I could have a similar look.
I also like the bald head with the soul patch look that he does...I think it takes a little attention away from the head if you're completely smooth on the whole skull like me. I don't grow good facial hair, but I can grow a decent soul patch.