We Might Be Drunk Ep 257: Roy Wood Jr.
10 snips
Nov 10, 2025 
Roy Wood Jr., a talented comedian and former Daily Show correspondent, shares his hilarious tour tales and insights on comedy. He reveals what it’s like to bomb on Star Search and opens up about his experience touring with Adam Sandler. The conversation dives into the intricacies of roast culture, the unique challenges of roasting athletes, and the differences in black versus mainstream roasts. Roy also discusses life after The Daily Show, his new book, and the importance of mentoring young comedians in today’s digital landscape.
AI Snips
Chapters
Books
Transcript
Episode notes
Green Room Faux Pas With Ron White
- Roy Wood Jr. recounts opening for Ron White and awkwardly offering him a ride, only to learn Ron had his own plane.
- The moment exposed Roy to 'rarefied air' and the private-jet lifestyle of established comedians.
Private-Jet Perks And A Green-Room Disaster
- Mark Normand describes touring with Adam Sandler: private jets, SUVs, and NBA-level perks like Under Armour access.
- He admits an embarrassing green-room bathroom incident that became lasting road lore.
Jamie Foxx's Roast Takeover Explained
- Roy recounts Jamie Foxx interrupting Doug Williams at a roast because Doug had been bragging backstage.
- He frames Jamie's onstage takeover as a clapback rooted in off-camera tension, not an unprovoked assault.
