The Sound of Young America is my favorite podcast. Not one of, is. I love the variety of guests and the questions always seem fresh even when the subjects are not. He didn't earn the title "America's Radio Sweetheart" for nothing.
One of my favorite interviews he did was with Shelley Berman. A legend with a history peppered with land-mines other interviewers would likely trod upon, yet Jesse managed to keep the interview interesting and coax a bit more than you'd expect from Shelley.
Here's Jesse, the host of TSoYA, being interviewed by the also awesome Claire Zulkey.