I can't think of a comedian that translates to long term enjoyment of a pin.
Cheech and Chong are close.
Rodney is for a different Generation.
George Carlin would be a Cult Favorite but fails Mainstream.
Modern Comedians usually are not funny.
There is just not anyone out there Comedian -Wise that could sustain a pinball Theme.
Do like Don Rickles though, how he insulted Famous People and they loved it.