DiscoverTrapitalHow Roy Wood Jr. Is Evolving His Comedy
How Roy Wood Jr. Is Evolving His Comedy

How Roy Wood Jr. Is Evolving His Comedy

Update: 2022-09-161


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

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Host: Dan Runcie, @RuncieDan,

Guests: Roy Wood Jr., @roywoodjr




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[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 producing shows as well, and how it's been like navigating these streaming networks, what their goals and incentives are. What his goals and incentives are and what he has seen from others in this space. We also talked about his upcoming movie Confess, Fletch. It's out in theaters on September 16th. It stars Jon Hamm. This is a reboot of the classic Chevy Chase Fletch movies from the eighties. So we talked about what to expect there, what he's excited about and more. Roy's good people, man, plain and simple. If you listen to the last conversation that him and I had, you know that if you've watched anything he's ever done on The Daily Show, ever seen him perform standup, you know that as well. Here's our conversation. Hope you enjoy it.

[00:02:30 ] Dan Runcie: All right. We are joined today by a return guest to the Trapital podcast, the one, the only, Roy Wood Jr. How are you doing man? 

[00:02:38 ] Roy Wood Jr.: You're back. I'm back. You're welcome. You're all welcome. I apologize in advance for my voice. There's things that happened this week that I did not plan on happening. And this is the result. It was either this or cancel, and I didn't want to cancel it. 

[00:02:54 ] Dan Runcie: No, I appreciate you. Hey, it's either this, or, you know, this is part of getting back on the road, right, 'cause I feel like the last time we talked, we were talking about what the other side of this whole pandemic was going to look like and what it was going to be like for comics returning to the stage. And now you're in it. What has it been like to return to the stage and with everything? 

[00:03:15 ] Roy Wood Jr.: What's wild is that I can't tell you too much. You know in 2022 I've only done four or five road gigs. Most of my gigs this year were COVID makeup dates from '21. So I've been blessed enough to be able to, you know, have a podcast that I'm able to do for myself, and sell a couple of scripts, and just create other revenue streams for myself, when the pressure to go back out on the road wasn't there. Also, creatively, I'm just in a different spot, bro. And I know that the stuff that I want to talk about, I don't know if the comedy club is the right place. It's part of the process creatively, but I just haven't been in a rush to get back out to figure it out yet, you know? It's been a really weird year for me in that the thing that I've done for 23 years is the thing that I did the least this year. And you know, that part of it's been really odd. It seems like the clubs are doing well though. You know, I still talk to a lot of comedians that are in the clubs because I'm still kind of that on the outside looking in. So I see all the comics who are touring, there's guys who I didn't know were headliners yet, but apparently, they are now. They're out there, they're doing their thing as well. So, you know, I'd say, all in all, it seems like the comedy club model got through it okay. But I don't know how sustainable it is as an entertainer to continue to be a part of this standup comedy model. You know, a lot of these new cats, you know, they're finding their own venues and they're figuring out their own way through the internet to get shit popping for themselves. But, you know, I will say this about standup. Since the shutdown, this idea of having one magical five-minute set on late night, and that being the thing that definitively becomes the new pivot point in your career, the likelihood of that happening is definitely less and less as the years go by.

[00:05:09 ] Dan Runcie: Interesting. I could only imagine how big of a life change it is for you. I remember you saying in the past, from when you started this once out of every 10 days, you were doing something on the road, right? Whether it was a standup show or something, and for you to be doing this completely different now, and just thinking about what the adapting is a complete life change, let alone anything on the business side of things.

[00:05:32 ] Roy Wood Jr.: Until the shutdown, until a federally mandated government shutdown, from 1998, I'd never gone more than 10 days without performing, period. 

[00:05:41 ] Dan Runcie: It's huge. 

[00:05:43 ] Roy Wood Jr.: And I've gone months. I look forward to it for months at a time. I don't have another gig right now. And I have a corporate gig in three months and I'm like, perfect, perfect because it gives me the time, it gives your brain the time to settle. I can only imagine, you know, when you look at guys like Chris Rock, who have said, you know, you need time to go away and live and see the world and experience things and have something to come back and report on. I understand that now.

[00:06:13 ] Dan Runcie: You also mentioned too, that there's material that you want to talk about, topics that you wa

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How Roy Wood Jr. Is Evolving His Comedy

How Roy Wood Jr. Is Evolving His Comedy

Dan Runcie