Comedian Robert Schimmel died last night from injuries suffered in a car accident.

Of all the comedians who have appeared on my radio shows through the years, no one turned tragedy into comedy like Bob. From his earliest days in the business, when he moved from New York to Los Angeles to take advantage of an offer to be a regular in a comedy club there, only to discover that the club had burned down, Bob lived a life you wouldn’t wish on anyone.

His son Derek died of cancer. Bob had a heart attack in 1998. Two years later, he was diagnosed with non-Hodgkins lymphoma. He left his wife for another woman, then moved back in with his wife (with whom he had four kids) before leaving her again to marry the other woman (with whom he had another kid), who he later divorced. Earlier this year, Bob contracted cirrhosis and Hepatitis C from a blood transfusion.

The remarkable thing about Bob was that he turned all of this into comedy — and when I say “all of it,” I mean he didn’t leave anything out. I wasn’t close with him off the air, but he sat in my guest chair many times over the years and never failed to make me laugh at the darkest humor I’ve ever heard. I loved having him on the air because he was able to weave prepared material from his act seamlessly into our conversations, which were never rehearsed or prepped in any way. Every hour was spontaneous and unique.

In his honor, I’ve dug two of those appearances out of my archives. The first is from February 3, 2000, when Bob joked about his heart attack and the accompanying sex pamphlet he was given by the American Cancer Society.

Listen.

The other is from September 13, 2002, when he was on about an hour before another guest, “Hollywood Squares” host Peter Marshall, which prompted Bob to tell a story about his trouble-making appearance on that TV game show. He also discussed a stunning request he got from his daughter, and the encounter between his mother and a porn star.

Listen to our conversation here.