Wayne Brady(I)

Spoofed his own harmless, sugary persona while appearing as a guest on Chappelle's Show (2003), portraying himself as a drug-dealing, pimping, murderous psychopath who terrorizes Dave Chappelle and others.

[on replacing Monty Hall as host of Let's Make a Deal (2009) in 2009]: They got me because they wanted someone a little edgier, but I get that it is daytime, so I am not going to say, 'Hey bitch, what's behind Door No. 1?' But it lets me push it as far as you can in the daytime schedule, because it is a Vegas audience.