W. Kamau Bell on Cosby, Comedy, and Father's Day

W. Kamau Bell on Cosby, Comedy, and Father's Day

Author: Paul Ollinger June 24, 2026 Duration: 27:50

I was most pleased to speak this afternoon with W. Kamau Bell, a Peabody Award and 4-time Emmy-winning comedian, filmmaker, and television host who is also a Celebrity Jeopardy champion!

He is best known as the creator and host of CNN’s United Shades of America on which he spent seven seasons traveling the country exploring communities, subcultures, and perspectives that often go overlooked. The show demonstrated his unique skill of helping people conduct difficult conversations without losing their sense of humor.

Not that he’s afraid to mix things up. Kamau’s 2022 HBO docu-series, We Need to Talk About Cosby dove deep into numerous allegations of sexual assault against legendary comedian and television icon, Bill Cosby, a comedian whose work Kamau deeply admired.

Kamau has a new podcast called Who’s With Me? on which he has already talked to Ted Danson, Delroy Lindo, Daveed Diggs, and Kristen Kish.

He spoke to me from his home in Oakland, CA where he lives with his wife and their three daughters. In this occasionally-serious, but most enjoyable conversation, we discuss:

* The difference between craft and character

* His love of podcasting

* Comedy nerd-ship

* The best part about Father’s Day

* And—most importantly— Dave Barry

Leave comments below. And follow / subscribe to this podcast.

Also subscribe to Kamau’s ‘Who’s With Me?’ Substack here and to Paul’s ‘Reasonably Happy’ Substack here.



Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 50

Reasonably Happy with Paul Ollinger
Podcast Episodes
Jared Dillian on ‘The Awesome Portfolio’ [not-audio_url] [/not-audio_url]

Duration: 45:04
My guest today is Jared Dillian, a former Wall Street trader, DJ, and the best-selling author of Street Freak, No Worries, and his new book, The Awesome Portfolio.Let me ask you a question: Can you let your investments r…
Dave Winfield, Baseball Legend [not-audio_url] [/not-audio_url]

Duration: 50:40
If MLB first-ballot Hall-of-Famer Dave Winfield’s story tells us anything, it’s that you can’t judge a person by how things appear on the surface.What we saw from the outside: a formidable 6’6”, 220 lb athlete who had ju…
Life in the Soviet Union (w/ Vitaliy Katsenelson) [not-audio_url] [/not-audio_url]

Duration: 58:21
Vitaliy Katsenelson grew up in the Soviet Union - in Murmansk, the largest city north of the Arctic Circle. Today, he is the CEO & Chief Investment Officer of IMA (Investment Management Associates).An award-winning write…
Senator Phil Gramm Dispels Economic Myths [not-audio_url] [/not-audio_url]

Duration: 1:00:09
This week, I sit down with Phil Gramm, economist, three-term United States Senator from Texas, former chairman of the Senate Banking Committee, and co-author of 'The Triumph of Economic Freedom: Debunking the Seven Great…
‘Young Money’ with Jack Raines [not-audio_url] [/not-audio_url]

Duration: 57:39
This week, I’m talking to Jack Raines, the guy behind the mega-popular Substack Young Money and author of a great new book called Young Money: A Field Guide to Wealth and Purpose in Your Twenties.After graduating from co…
Can You Fake Happiness? w/Beth Cabrera [not-audio_url] [/not-audio_url]

Duration: 44:08
“People do not decide their futures: they decide their habits and their habits decide their future.” – F.M. AlexanderIf you want to improve, be kind to yourself. That’s the message from this week’s guest, Dr. Beth Cabrer…
Freeze the Rent! And Other Silly Policies ( w/ Paula Pant) [not-audio_url] [/not-audio_url]

Duration: 1:12:21
Last week, I received a bill from New York City for $71,1783.16. It was the balance due for my Non-primary residence surcharge, aka the pied-à-terre tax that is a premium on top of the $55k or so we pay in regular, old f…
Nobel Prize Winner on "Moral Economics" [not-audio_url] [/not-audio_url]

Duration: 49:36
This week, I sit down with Dr. Alvin Roth, Nobel Prize-winning economist, Stanford professor, and author of Moral Economics: From Prostitution to Organ Sales, What Controversial Transactions Reveal About How Markets Work…
How Empathy Is Destroying Western Civilization (with Gad Saad) [not-audio_url] [/not-audio_url]

Duration: 1:10:26
In this episode of Reasonably Happy, I sit down with Dr. Gad Saad, an evolutionary behavioral scientist, longtime professor, and author of the New York Times bestseller Suicidal Empathy: Dying to be Kind. Gad lays out wh…