Roy Wood Jr. Discovered His Love of Comedy from Heckling His Opponents in High School Baseball

Roy Wood Jr.’s first unofficial, unpaid comedy gig was as roast master for a youth baseball team in Birmingham, Alabama — Jeff Ross must have been booked.

Talking trash has always been a significant element of organized athletics for stars and benchwarmers alike, though more so for the latter. After all, if you can’t run the bases, at least you can run your mouth. Wood, the longtime Daily Show correspondent and prospective Daily Show host, never had a future in professional baseball, but as he discovered during his time in the dugout while riding the bench on his high school team, comedically chirping at opposing players isn’t all that different from stand-up comedy — only with more rhymes and puns related to the words “pitcher” and “batter.”

On the most recent episode of the Renaissance Man podcast hosted by former NBA player Jalen Rose, Wood opened up about his comedy origin story as the benchwarmer who could get inside opponent’s heads with hilarious burns, though Wood preferred the title “Team Psychologist.”

Wood also discussed how, shortly after his high school trash-talking days, he started his stand-up career in earnest, but not before nearly derailing it with a dumb decision. “I got arrested for stealing clothes,” Wood explained. “I was 19 years old, and I was told, ‘Yeah, you’re going to go to prison. You’ll probably do a year, but they’re going to give you five.’” Thankfully, Wood was shown leniency and avoided jailtime, but the feeling of desperation and despair didn’t leave him.

“That’s where guts came in to (start doing) the open mics … a sense of hopelessness and the presumption that my life was over,” said Wood. “The truth was that was just the rock bottom, ground zero reason that I needed to get me back on the path.” Wood worked his way up through the amateur level, taking gigs across the deep south and even sleeping in bus stations between performances. Then, in 2015, 20 years after Wood discovered his gift of gab in Birmingham dugouts, he joined The Daily Show and mocked his political opposition with the same cutting wit that he once used to rattle opposing pitchers.

“It’s been a blessing to go from sleeping in a bus station to roasting the president at the Correspondents’ Dinner with my mother in attendance,” Wood said. In terms of trash talking, telling Joe Biden to his face that, “Mr. President, I think you left some of your classified documents up here. … I’ll put them in a safe place, he don’t know where to keep them,” has to be somewhere in the ballpark of a World Series win.