How Roy Wood Jr. Is Evolving His Comedy Trapital

Returning to Trapital for a second time is comedian Roy Wood Jr. We last spoke in mid-2020 when lockdowns curbed his usual comedy performance routine. On the outside, it might not seem Roy has changed much since our first convo — he’s still a regular on The Daily Show with Trevor Noah — but internally, Roy is amidst another career evolution.

Roy made a successful comedic career — three specials on Comedy Central over a five-year span — out of finding unique angles to discuss external events such as news and politics. But now, Roy wants to talk about himself. Spurred by an appearance on PBS’ “Find Your Roots”, Roy is more introspective about the relationship with his father, a civil rights activist, and how it influences raising his own son.

How and where Roy delivers this refined message hasn’t been decided yet. For now, Roy is taking time for himself to think through how he’s changed, and so has comedy and the entertainment industry at-large. In our discussion, Roy hinted at some of those major changes. Here’s what we covered:

[3:15] The state of live comedy in 2022
[5:32] Roy’s insane performing streak from 1998-2020
[6:27] Why the comedy club isn’t the right venue for Roy right now 
[11:45] Comedian expectations have changed 
[13:35] Morality vs. profit 
[17:05] Roy’s partnerships
[18:42] Roy’s criticism of Netflix and streaming
[26:27] The new superstar is an assemble cast 
[31:08] How Roy chooses comedic topics
[34:43] Roy’s most personal joke
[35:24] How much does Roy’s son know about his comedy career? 
[37:39] How Dick Gregory changed Roy’s life
[40:48] Roy starring in Confess, Fletch movie


Listen: Apple Podcasts | Spotify | SoundCloud | Stitcher | Overcast | Amazon | Google Podcasts | Pocket Casts | RSS

Host: Dan Runcie, @RuncieDan, trapital.co

Guests: Roy Wood Jr., @roywoodjr

 
Sponsors:
 
MoonPay is the leader in web3 infrastructure. They have partnered with Timbaland, Snoop Dogg, and many more. To learn more, visit moonpay.com/trapital
 
Enjoy this podcast? Rate and review the podcast here! ratethispodcast.com/trapital
 
Trapital is home for the business of hip-hop. Gain the latest insights from hip-hop’s biggest players by reading Trapital’s free weekly memo.

TRANSCRIPTION
[00:00:00] Roy Wood Jr.: You can be funny, you can get away with being funny for a little while, but true career longevity as a comedian, I believe, you have to make people feel, you have to give them an emotion. Sooner or later they have to leave feeling a certain way. It's not just a matter of the tactile Xs and Os of did they laugh at the setup? Did they laugh at the punchline? Okay, next joke. It's what are you infusing into that person's heart on the backside of this experience that you all had together on stage for an hour.  
[00:00:36] Dan Runcie: Hey, welcome to The Trapital podcast. I'm your host and the founder of Trapital, Dan Runcie. This podcast is your place to gain insights from executives in music, media, entertainment, and more, who are taking hip-hop culture to the next level. 
[00:00:56] Dan Runcie: Today's guest is Roy Wood Jr. This is his second time back on the podcast. The first time we recorded a podcast was back in the middle of 2020, middle of the pandemic. And we talked a lot about how the closure of comedy clubs and the closure of everything was affecting his life as a comedian and what he saw the world would be like on the other side of the pandemic. And now we're starting to be here, so it was a great opportunity to check in, hear how things are going for him. And we talked a lot about how the past couple of years have reshaped his perspective on the type of message that he wants to be able to. What are the best venues to do that and how he might change his approach up a little bit in the next few years. We also talked about streaming and what it's been like from his perspective as someone that is acting in movies, acting in TV shows, writing and produ