It's been kind of a tradition of mine, I love to end the day with his monologue and I've been doing it for years. His humor is right up my alley and rarely do I ever find myself laughing out loud from something on TV, but he gets me laughing every time. It's the best way to end the day. I love how he's often the butt of his own jokes. If you haven't given him a chance, you need to. Jenny is also a Conan lover. I have definitely found the woman of my dreams. In fact Conan O'Brian was one of the topics on our first date! Awwwww!
Actually, Jenny and I waited like 2 hours to see him in NYC and we got cut from the line last second. It was heart breaking, but we're going back some day and we're going to try again!
This is borderline "too stupid", but it still makes me laugh: Stupid, but Funny
On a related note, I think Jay Leno has gotten really lazy with his jokes. I can't even watch his show anymore. JayWalking, where he goes out and finds ditsy people to make up silly answers to easy questions is a perfect example. And some people love it. I don't get it. I also hate that he's always bragging about his cars, and he seems to set himself up so that he gets to talk about how wealthy he is. BO-RING!
David Letterman is a classic, but I don't watch him either. He was even in the same Fraternity (Sigma Chi) that I was in, back in the frat days, but I don't speak publicly about that! :)