208. Kevin Fredericks: How To Make A Comedy Show About Grief

Lin-Manuel Miranda called Mike up a few months ago to say he wanted Mike to meet comedian and author Kevin Fredericks. This week, Mike sits down with him for the first time and the two of them break open Kevin’s new solo show “Grief Sucks,” which Kevin wrote about his brother’s death. The two discuss how to make the darkest topics funny, how being a comic is mostly about failing and then doing it again anyway, and what to do when you accidentely cry on stage. Plus, some thoughts about the Oreos you eat on the way to eat Oreos. Please consider donating to Storm DeBarge's non-profit work (CashApp: $bijan1996) Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

The last time comedian Chris Fleming was on Working it Out, the episode was titled “He Should Be Way More Popular.” In the 2 years since then Mike’s wish has come true. Chris and Mike chat about the pros and cons of having a higher profile in comedy, including the protective steps needed to avoid legal action from Adam Driver over a bit. Mike also takes the chance to respond to the shots Chris takes at Mike in his new HBO special Live at the Palace, and Chris talks about getting glared at by Ryan Gosling. Plus, Mike and Chris work out lots of new jokes about drum circle friend groups, hotel smells, and dog DNA tests. Please consider donating to Planned Parenthood Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

(Recorded February 2025) Nathan Lane sits down with Mike and recounts moments from his legendary career — discussing what it was like to work with Mike Nichols, Elaine May, and Robin Williams. He shares what he likes most in a director, who he’s jealous of, and what he remembers of twenty-something year old Mike. Plus, an incredible story about working with Joaquin Phoenix on the film Beau is Afraid. Please consider donating to Broadway Cares Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

(Recorded February 2025) Nathan Lane sits down with Mike and recounts moments from his legendary career — discussing what it was like to work with Mike Nichols, Elaine May, and Robin Williams. He shares what he likes most in a director, who he’s jealous of, and what he remembers of twenty-something year old Mike. Plus, an incredible story about working with Joaquin Phoenix on the film Beau is Afraid. Please consider donating to Broadway Cares Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Mike welcomes author, actor, and filmmaker Cazzie David to the podcast and right away, Mike challenges the notoriously misanthropic Cazzie to list five things she loves. It takes a while. Then, Cazzie breaks down her new book of essays, Delusions, which she says her mom found “disturbing,” and Cazzie talks about co-directing the indie film I Love You Forever. Plus, Cazzie’s close call with a rabid bobcat, and why Mike wants his journals burned after he dies. Please consider donating to The Legal Aid Society Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Working It Out all-timer Taylor Tomlinson returns to the podcast this week on the heels of the release of her new Netflix special, “Prodigal Daughter.” Mike and Taylor talk through what they do when they get stuck on a bit, what they’d do if they found out they were dating their cousin, and how being a stand-up is sometimes just telling 300 people a secret you weren’t ready to share. Plus, lots of new jokes about sex dreams, lovebombing, and baby names. Please consider donating to the Palestine Children's Relief Fund Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Ali Siddiq is one of the most prolific storytellers in comedy. Although they work in a similar format, Ali and Mike’s paths have never crossed until now. Now they sit down to discuss the nuances of comedic storytelling, including how to make specific topics relatable to audiences, and Ali explains how he made his own path in comedy after serving six years in prison on drug charges. Plus, Ali and Mike, both parents of swimmers, share war stories from swim meets. Please consider donating to the Houston Food Bank Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Beloved British comedian James Acaster and Mike have never met but they have a lot in common, including brushes with death early in their lives that influenced their comedy. James and Mike discuss James’s experience with hecklers, which is the subject of James’s new special Hecklers Welcome. Plus, James talks about having Robert De Niro on his podcast Off Menu, and he shares the best pre-show ritual that Mike has ever heard. Please consider donating to Friends of the Earth Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Best of WIO: Bob Odenkirk (Recorded July 2025)Bob Odenkirk was already a comedy legend (SNL, The Ben Stiller Show, Mr. Show with Bob and David) before he took a left turn into dramatic acting with Breaking Bad and Better Call Saul. Now he’s entered yet another new phase as an unlikely action star in films like the Nobody series. Bob sits down with Mike to discuss how anger works in comedy and action films, the stress of making Better Call Saul, and the time Bob played Mike’s brother on a TV pilot.Please consider donating to Food on Foot Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Connor Ratliff is a beloved cult comedy figure known for his award-winning podcast Dead Eyes and his long-running live show/YouTube series The George Lucas Talk Show. He also played an improv student in Mike’s film Don’t Think Twice, which is a bit of a winking joke because Connor is one of the most experienced and revered improvisers on the scene. Mike and Connor go deep on improv comedy process, Connor shares some of his most devastating audition stories, and the two take a phone call from their mutual friend Chris Gethard.Please consider donating to Paws NY Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.