How Roy Wood Jr. Is Evolving His Comedy — For Himself, Not Others

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:

0:53 The state of live comedy in 2022
3:47 Roy’s insane performing streak from 1998-2020
4:54 Why the comedy club isn’t the right venue for Roy right now
10:39 Comedian expectations have changed
12:47 Morality vs. profit
16:42 Roy’s partnerships
18:42 Roy’s criticism of Netflix and streaming
26:35 The new superstar is an assemble cast
29:09 How Roy chooses comedic topics
33:24 Roy’s most personal joke
36:36 Where Roy’s comedy is evolving
38:00 How much does Roy’s son know about his comedy career?
39:57 How Dick Gregory changed Roy’s life
44:00 Roy starring in Confess, Fletch movie

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