Second City alum David Steinberg is on Charlie Rose right now, making some very interesting observations about how sometimes, more "personal" comedy, like Dave Chappelle on Comedy Central can find a wider audience than "generalized" comedy on the big networks.
He's also talking about finding one's authentic self, and how timing is so important in comedy in so many ways - the literal timing of joke delivery, the timing in a comedian's life and creative development, the synchronous timing with the Zeitgeist, and so on.
A huge issue I've been thinking about since last week's open mic - letting the audience know you enough to know they can trust you, so they can be comfortable with you delivering riskier jokes. I did three bits last week, and spent the entire hour before my five minutes obsessively reordering them. It was ridiculous. I kept writing "Sunburned," "Inappropriate," and "Uncool Job" in a different order again and again. (Yeah, you should have been there for my proofreading joke...it left the room in tatters.)
My first instinct was to put a safer and more self-deprecating bit first, before going to something a bit sharper, but at the last minute I switched the order, and led off with the edgier joke, which got a fairly flat reaction. Honestly, as soon as the words started coming out of my mouth, I had this creeping feeling up the back of my neck, and I thought "Oh, crap, I haven't let these people know me enough to let me get away with saying something this barbed without thinking negatively of me." I knew it, but I had to keep plugging along. I know better for next time.
This has been your semi-regular installment of comedic navel-gazing. You are now free to explore other internet amusement options that are actually interesting.