With his fifth appearance, comedian Alex Edelman is the most frequent guest on Working It Out. Since his last appearance, Alex won an Emmy for his HBO stand-up special Just For Us, which Mike was a producer on. Now Alex is back on the road with a new hour of comedy, including a just-announced visit to Carnegie Hall. Alex discusses Boston sports memories, whether AI will replace comedians, and grieving the death of his creative collaborator Adam Brace. Plus, Alex’s rocky stint as a hospital clown, and his new job as a writer and actor on Greg Daniels’ highly anticipated follow up to The Office: The Paper.

See Alex at Carnegie Hall

Please consider donating to Memorial Sloan Kettering Cancer Center

Chelsea Handler has achieved massive success, from her latest Netflix special The Feeling to her worldwide tours to her Las Vegas residency. But as she discusses with Mike, and details in her new book I’ll Have What She’s Having, she wasn’t always on top of the world. Chelsea tells Mike about bombing badly at Just For Laughs, and how some advice from Jane Fonda helped her during a difficult time. Plus, the story of when Chelsea unintentionally drove a giant bag of cocaine across the country, and why she felt compelled to confront Woody Allen with a very dark joke.

Please consider donating to the Carter Center

This week comedy duo Jane Wickline and Liva Pierce (together known as Dukes) join Mike on the podcast. The three discuss how The Graduate brought Jane and Liva together, their unlikely porn preferences, and what happened when Jane showed up to her SNL audition early. Jane and Liva work out a couple songs from their touring show and for the first time ever on Working It Out—Mike’s jokes get set to music.

Please consider donating to Samir Foundation

Get tickets to Dukes