🎧 Hear the full interviews on The Plug w/ Justin Jay → https://www.theplugwithjustinjay.com/
🎤 Exclusive conversations with celebrated artists, actors, musicians & creators.
Subscribe now →https://www.youtube.com/channel/UCNH5UGRKI5E1AUBWAk-OkrA?sub_confirmation=1

Roy Wood Jr. isn’t afraid to joke about the things most comedians won’t touch. From race and politics to everyday realities of life in America, his comedy balances honesty, risk, and sharp wit. Whether on stage, as a longtime correspondent on The Daily Show, hosting the White House Correspondents’ Dinner, or guest-hosting the topical show Have I Got News For You (airing on HBO and CNN), Roy finds humor where most wouldn’t dare go.
In this episode of The Plug with Justin Jay, Roy opens up about:
- How race shapes his stand-up and why he leans into delicate topics
- The challenge of writing sharp political jokes without letting them get “weaponized” online
- Behind the scenes of The Daily Show and the Correspondents’ Dinner
- The risks of critiquing both the Black community and progressive politics
- Personal stories from Finding Your Roots and how family history informs his material

Roy Wood Jr. doesn’t just tell jokes — he creates conversations. This interview is an unfiltered look at the craft, risks, and responsibility of using comedy to explore race and truth in America.

00:00 Roy Wood Jr. Interview Intro
00:27 Has 2023 Changed Everything for Roy?
00:40 The Grind of Stand-Up Comedy
01:59 Why Comedy Feels Like Jack Bauer in 24
02:39 Inside the White House Correspondents’ Dinner
04:43 Can Comedy Really Change Minds?
06:45 What Roy Learned on The Daily Show
09:18 Balancing Nuance in Political Comedy
12:10 Hosting vs. Correspondent: What’s Harder?
13:01 Race, Risk & Critiquing Both Sides
14:13 Breaking Down *Imperfect Messenger*
17:15 Writing Jokes on Delicate Topics
18:46 Internet Killed the “Incubation Period” for Comedy
20:00 When Roy Knows He’s Won the Crowd
22:35 Crafting Jokes for the President
24:32 Personal Stories from *Finding Your Roots*
26:15 Race, Trauma & Healing Through Comedy
27:15 Future Stand-Up Specials & Fatherhood Themes
28:13 Roy Shouts Out Pete Davidson’s *Bupkis*
29:08 Comics Roy Respects & Emerging Voices
30:01 Final Thoughts on Comedy & Free Speech
30:49 Closing Thanks to Roy Wood Jr.

About The Plug
---
The Plug w/ Justin Jay is a bi-monthly arts and culture podcast featuring unfiltered, long-form interviews with the artists, entertainers, and innovators shaping today’s world. Each episode explores career challenges, inspirations, and the stories behind music, sports, design, and politics.

---
Follow the audio podcast of The Plug w/ Justin Jay every other Thursday → https://www.theplugwithjustinjay.com

---
Topics: music production, New York City history, hip-hop history, creative process, professional surfing, comedy, photography, arts & entertainment

---
Subscribe & Stay Connected
• YouTube → https://www.youtube.com/channel/UCNH5UGRKI5E1AUBWAk-OkrA?sub_confirmation=1
• Website → https://www.theplugwithjustinjay.com
• Apple Podcasts → https://podcasts.apple.com/us/podcast/the-plug-w-justin-jay/id1517322794
• Spotify → https://open.spotify.com/show/3M3BwnadvgbuwtErUHN1pl
• Instagram → https://www.instagram.com/justinjayphoto/

---
• Have comments, feedback, or guest suggestions?
We’d love to hear from you!
Email The Plug w/ Justin Jay → theplugpodcast.jj(AT)gmail.com