Roy Wood Jr. on the Lessons that Last

Roy sits down with Rainn PLUS an excerpt from "The Man of Many Fathers"

Salutations to all you sons, daughters, and soul apprentices out there—

This week on the Soul Boom podcast, Rainn sits down with comedian, writer, and cultural truth-teller Roy Wood Jr. — whose new book, The Man of Many Fathers, is a moving meditation on fatherhood, mentorship, and manhood.

In this episode, the two talk about fatherhood as a spiritual apprenticeship — the ways men inherit not only wisdom but also wounds, and how healing those patterns can help us raise the next generation with more honesty, kindness, and heart. They trade stories about comedy as therapy, laughter as revelation, and what it means to find fathers in unlikely places: coaches, barbers, teachers, neighbors, and friends.

Roy Wood, Jr. with Roy Wood, Sr. From Roy’s Twitter.

At its heart, The Man of Many Fathers is Roy’s love letter to the village that raised him — and the village he hopes to build for his own son. His own father, Roy Wood Sr., was a legendary journalist and radio host who helped chronicle the civil rights movement, a man of immense intellect and moral courage. Roy Wood Sr.’s résumé in civil rights journalism is one of those unsung American stories. He covered the Soweto uprisings in South Africa, the Rhodesia/Zimbabwe civil war, and the Vietnam War — focusing specifically on the Black platoons who were dying faster than their white counterparts. He hosted a radio show with Ernie Banks, became the first news director at Chicago’s Black-owned radio station WVON, and even hired Don Cornelius — then gave Cornelius $500 to help get Soul Train off the ground. He later turned down a producer credit, which, as Roy Jr. put it, proved just how “old school” his father was.

That legacy followed Roy Jr. everywhere, whether he wanted it to or not.

But Roy Sr. died when Roy Jr. was just sixteen—at a time when the two were still finding their rhythm as father and son. He never got the chance to finish that conversation: the long, unfinished dialogue between a father and a son trying to understand each other. In a way, this book is how he continues it.

Some of his father’s journalistic precision clearly rubbed off. Roy inherited his dad’s instinct to tell the truth, but he learned to do it through laughter—turning his reporting on the absurdities of American life into stand-up, sketch, and satire. From the newsroom to the green room, the impulse is the same: to make sense of chaos with clarity and compassion.

Roy Wood Jr. on The Daily Show. Credit: Comedy Central

And where his father’s lessons left off, others stepped in. A high school coach, a radio mentor, a kind cafeteria cook, a dishwasher philosopher — more than a dozen men in all — helped shape the person he became. Together they formed what Roy calls his “village of fathers,” a mosaic of masculine wisdom gathered from every corner of his life.

Like Rainn, Roy uses humor to excavate the soul — both men turning the absurdity of life into a search for meaning. One does it through the lens of faith and the soul’s journey; the other through the lineage of fathers, mentors, and everyday saints. In the end, both are talking about the same revolution: one of the heart.

So this week, along with the episode, we’re sharing a brief excerpt adapted from Roy’s The Man of Many Fathers — a letter to his son that begins, as all real wisdom does, in humility.

Excerpt from The Man of Many Fathers

By Roy Wood Jr.

Dear Son,

It must have been 2006, maybe 2007, about ten years before you were born, when I ran into actor and comedian Brandon T. Jackson on Father’s Day in Chicago’s Midway Airport. I didn’t know Brandon that well at the time, but we were both on the Los Angeles comedy scene pretty heavy. We stopped and spoke to one another. Had we seen each other anywhere in Los Angeles, this same moment would’ve warranted nothing more than a brief head nod out of respect.

But stand-up comedy is such an isolating, nomadic life, especially on travel days. When you see another comedian in the airport it feels good, even if you don’t know them that well. You are in a place with thousands of strangers, and you have found the one person who understands exactly what you’re going through. A moment that would be a passing head nod on the streets of Hollywood becomes a full-on conversation in an airport.

Brandon and I talked while walking to one of the little airport convenience stores. Like most comedians, we commiserated over our industry gripes and career challenges. “Drama bonding” is what I like to call it. I was struggling financially after taking a moral stance against a comedy club booker who accounted for 40 percent of my road bookings. Brandon, meanwhile, was in the middle of multiple auditions for a pretty major comedy film. He was nervously optimistic he would get the role but also worried about what booking the film would mean for his availability for the more reliable television roles during that same time. I politely poked and prodded him for more information about the film to help him weigh the pros and cons, but all he could tell me was “It’s a comedy with Ben Stiller.”

Once inside the store, Brandon made a beeline to the greeting-card rack and began frantically looking through what was left of the Father’s Day options on sale. The rack was barren like grocery store shelves when people make a run for the milk and bread before a hurricane. Between topics, Brandon would pull a Father’s Day card off the rack, read it, then ask me for my opinion on the prose inside the card.

“Getting this to my pops as soon as I land—I want a card that really says something,” he said, while handing me a card. “What do you think about this one?”

My responses lacked the reassurance he was looking for, so he’d put each card back on the rack and search for another. We did this for about three or four greeting cards, and every time my reaction was the same. Humdrum. Take or leave it.

Brandon got frustrated and looked at me like a date who couldn’t decide where to eat. He fired off sarcastically, “Well damn, what kind of card do you get your father?”

I thought about it for what was probably far too long and replied, “I don’t think I have ever bought a Father’s Day card.”

Brandon froze. It was one of those moments when you know you could ask a follow-up question if you wanted, but you also don’t know where the answer is going to take you and you’ve got a flight to catch.

Presumably pressed for time, Brandon passed on a follow-up, and the conversation returned to the usual industry fodder. Shortly thereafter, we shook hands, said our goodbyes, and headed off to our respective gates. Back to the comforting isolation that is traveling for a living.

I have never forgotten that conversation.

It was the first time as an adult when I actually had to stop and think about what my relationship with my father was like. Thank God Brandon was running late for his flight. There’s no telling how I would have answered his follow-up question…

Son, when you were born, I went through something that day. Having a child is interesting because the first thing you do is think about all of the things you’re going to do with them, the way you’re going to throw a ball together or learn chess together. You start making plans for education and social engagement. “I’m so full of knowledge!” you excitedly think to yourself. “Which piece of knowledge will I pass down to him first?” After those feelings subside, you think about how you are going to teach this child values. That, in turn, forces you to think about how you were taught values—to audit your own parents.

I sat back in the delivery room just holding you and thought about the time that I had with my father, who died when I was sixteen. I didn’t feel like I got as many lessons from him as I plan to give to you…

The more I thought about simple life lessons I wanted to teach you, like the value of saying please and thank you and “Yes, sir” and “No, sir,” the importance of chivalry, and my approach to avoiding violent situations, the more I realized I did not learn most of these things from my own father. I learned these lessons from other men who came in and out of my life…

As I sat in the delivery room holding you in 2016, I reflected on how lucky I have been to have so many men over the decades who have imparted wisdom, either knowingly or unknowingly…

That’s why I’m going to jump at any opportunity to get worthy men in front of you as soon as possible. Fatherhood is a job that’s bigger than any one man…

It is their wisdom that I will use to help construct a village for you, so that one day when you finally meet Brandon T. Jackson in an airport, you’ll know exactly what kind of Father’s Day card to help him find.

Love,
Dad

P.S. Brandon booked the movie. When you get a little older, son, check out Tropic Thunder. Still a classic.

Adapted from The Man of Many Fathers by Roy Wood Jr. Copyright © 2025 by South Park & Princeton Productions, Inc. Published in the United States by Crown, an imprint of the Crown Publishing Group, a division of Penguin Random House LLC.

ROY WOOD JR. is a comedian, writer, and Emmy-nominated producer whose sharp wit and deep empathy have made him one of the most compelling voices in American comedy. A longtime correspondent on The Daily Show with Trevor Noah, he also hosted the White House Correspondents’ Dinner to its highest ratings in years and produced the acclaimed PBS documentary The Neutral Ground.

Beyond the stage, Roy’s work bridges humor and humanity—using laughter to confront issues of race, class, and justice with clarity and compassion. His philanthropic efforts support literacy, disability inclusion, and reentry programs in his hometown of Birmingham, Alabama, where he continues to invest in community empowerment and opportunity.

His book, The Man of Many Fathers, is a moving exploration of the men who shaped him after losing his own father, legendary journalist Roy Wood Sr., when he was sixteen. Through storytelling that’s equal parts hilarious and healing, Roy carries forward his father’s legacy—seeking truth, building community, and finding the soul beneath the punchline.