I need to start spending more than five minutes on thinking up titles for lists.
Yes, this is a list about clowns. Not just in any role though: strictly those that appear in their own game as playable characters. You can pull a thousand different violent, evil, insane clowns from this medium; in fact, you're almost as likely to bump into a psychotic thug in jovial greasepaint in a video game as are you at the Gathering of the Juggalos. Instead, I want to recognize the few clowns out there that - as the (or a) playable character - are meant to be at least sympathized with to some extent, if not worth actively rooting for.
There'll still be a few decidedly unmerry-andrews here and there on this list but overall these are clowns of renown. Fools that are cool. Jesters that were never... bester. Let's just get on with this.
(As always, feel free to suggest your own contributions to the list in the comments below, and I'll be sure to add and accredit them appropriately. I imagine I must've purposely avoided a lot of clown games as a kid on principle.)