Jay Leno is the most successful of all the late night talk show hosts but that doesn't necessarily mean he's the funniest of all them. Middle aged people tend to prefer him in the Tonight Show slot more then when Conan O'Brien had it since they like safe humor instead of anything truly inventive. Most of Leno's best skits are just the same skits he does over and over again like Jay Walking and Headlines. Which are decent skits to do but it's not like he's coming up with completely new and inventive skits that make you laugh, he just goes to the same well over and over again. I'm not saying Leno is bad but if you were to rank the funniest moments in late night talk history chances are he wouldn't have as many things on the list as Conan or David Letterman would.
Review of The Tonight Show with Jay Leno
