My dad encouraged us to fail. Growing up he would ask us what we failed at that week. If we didn't have something he would be disappointed. It changed my mindset at an early age that failure is not the outcome failure is not trying. Don't be afraid to fail.
The comedians I liked were Bill Cosby and Steven Wright like just always as a comedic actor. I always liked Gary Larson who's really funny for a cartoonist obviously.