Money, Family & Comedy w/Roy Wood Jr.

✍️ Follow Paul Ollinger on Substack by clicking here ✍️My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can still hit hard. A native of Birmingham, AL, Roy has that rare ability to make you laugh while also making you think—whether he’s talking about race, class, media, relationships, or the strange little hypocrisies we all live with. In addition to The Daily Show, Roy has performed on The Tonight Show, The Late Show with David Letterman, BET’s Comic View, Conan, and many other top TV programs. He is now the host of the CNN current events-comedy show, Have I Got News for You. His 2025 memoir, The Man of Many Fathers explores—among other things—Roy’s complicated relationship with his father, Roy Wood, Sr., a civil rights journalist and African American radio pioneer.Today, Roy and I talk about money, family, fatherhood, and we go deep on the craft of comedy.Speaking of comedy, see my upcoming shows below. Save the date / buy your tickets!COMEDY NEAR YOU - GET YOUR TICKETS!* May 16: QED, Astoria Queens, 9:30* May 20: Dunwoody Country Club (members only)* May 21: Atlanta Punchline - ON SALE* May 22-23: DC Comedy Loft ON SALE* June 4: Atlanta Athletic Club (members only)* June 19-20: Comedy Catch, Chattanooga ON SALE* June 25: Couples Therapy Comedy at West Side Comedy Club, NYC* July 21: The Venice West, Los Angeles - On Sale soon* July 23: Cobbs Comedy Club, San Francisco - ON SALE* Aug 1: Sticks and Stones Comedy Club, Southampton, NY -* Aug 8: Atlanta Country Club (members only)* Aug 13-16: Headlining McCurdy’s in Sarasota, FL - ON SALE* October 15: Capital City Country Club (members only) Get full access to Reasonably Happy at words.paulollinger.com/subscribe