Roy Wood Jr. | Father Figure (Episode 593)

Roy Wood Jr. (@roywoodjr) was on Variety’s 10 Comics to Watch For list in 2016, is currently a correspondent on The Daily Show with Trevor Noah, and is the star of Father Figure on Comedy Central.

The Cheat Sheet:

  • Learn how a youthful indiscretion was “the most important thing” that led Roy Wood Jr. to pursue a life of comedy.
  • Discover how a forgiving journalism school and a deal with his mother gave Roy’s comedy career the low-stakes structure it needed to grow early on.
  • Find out how Roy took being booed off stage as an opportunity to learn rather than as a soul-crushing defeat.
  • How does a performer stay visible and relevant in such a hyper-competitive landscape?
  • Understand how comics practice nuances you may not even notice to punctuate their presentations (and how Roy learned to lose some of his bad habits by observation).
  • And so much more…

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Sure, everybody has regrets. Who among us hasn’t wished for a time machine to go back and erase mistakes of the past? Not comedian Roy Wood Jr., who credits being arrested for shoplifting as a teenager as “the best thing” that ever happened to him.

Now a regular correspondent on The Daily Show with Trevor Noah, one of Variety’s 10 Comics to Watch For in 2016, and the star of Father Figure on Comedy Central, Roy has become a familiar face poised to become even more familiar. He joins us to talk about how he got where he is today and what we can expect from him in the future. Listen, learn, and enjoy!

Please Scroll down for Full Show Notes and Featured Resources!

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More About This Show

When a minor crime spree landed young Roy Wood Jr. in a holding cell to await sentencing, he was certain a lifetime in prison would be his fate — a terrifying prospect when gritty HBO drama Oz was his only exposure to what this might entail.

“The deal I made with myself was, ‘Before I go to prison, I’m going to do everything I’ve ever wanted to do in life,'” says Roy. “And comedy was on the list. It’s really just that simple. That was something I always wanted to try, but never had the guts to do when I was in high school.”

While Roy was in gifted programs throughout his early education, it wasn’t until high school that he really had a chance to settle in one place for more than two years. It’s when he first started to feel like he fit in anywhere, and he was loath to ruin it by failing at comedy in front of his new peers — until the prospect of prison.

“When you’re faced with being stabbed and raped eventually in federal prison…comedy becomes a lot less daunting of a task!” says Roy. “Getting arrested, hands down, was the best thing that ever happened to me — because it was an ultimate pivot point in my life. It didn’t take two days for me to realize what the hell I wanted to do. I had a plan laid out of how I wanted to go about doing it, and three years later I had a college degree and a decent career.”

Roy knows he was lucky the journalism school he attended at the time of his indiscretion didn’t expel him, because it allowed him a low-stakes structure to try his hand at comedy. He didn’t have to go all in to make it work, but a deal with his mother upon graduating ensured that he was able to experience growth in his career every year without getting sidetracked.

“To me, [comedy] had always been full time,” Roy says. “I never said ‘yes’ to something in the place of comedy. Comedy supercedes everything…I just rolled into a guy willing to drive anywhere to perform for anybody. If you have a stage and a microphone, I’m there. I’ll sleep in my car; I’ll figure out the rest of it on the back end.”

Novice comedians in larger cities often enjoy each other’s camaraderie while taking the rough steps to get established. But Roy’s nomadic education prior to high school may have better prepared him for the lack of such a support system in the southern comedy scene.

“’98 or ’99, if you wanted to get on stage every week, you had to drive four hours,” says Roy. “There was none of this being in the same city all month — I didn’t have that luxury. I wish I did!”

Listen to this episode of The Art of Charm in its entirety to learn more about why a comedian who bombs in an opening slot should stick around for the whole show, how dissecting differing comic styles helps Roy better hone his own style, what bad habits Roy has learned to drop while performing, how a comedian without the camaraderie of other comedians quantifies getting better, what simple goals can help a novice comedian grow, why a ‘no” is better than being ignored, how to use social engineering to get gigs, ways Roy has to skip a level, and lots more.

THANKS, ROY WOOD JR.!

If you enjoyed this session with Roy Wood Jr., let him know by clicking on the link below and sending him a quick shout out at Twitter:

Click here to thank Roy Wood Jr. at Twitter!

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Jordan Harbinger - author of 924 posts on The Art of Charm

Jordan Harbinger has spent several years abroad in Europe and the developing world, including South America, Eastern Europe, and the Middle East, and speaks several languages. He has also worked for various governments and NGOs overseas, traveled through war zones, and been kidnapped -- twice. He’ll tell you the only reason he’s still alive and kicking is because of his ability to talk his way into (and out of) just about any type of situation. Here at The Art of Charm, Jordan shares that experience, and the system borne as a result, with students and clients.

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