Mick Unplugged: "The Heart Behind the Humor with Roy Wood Jr."

Podcast Host: Mick Huntoon
Guest: Roy Wood Jr.
Date: November 13, 2025

Episode Overview

This episode of Mick Unplugged delves into the journey and purpose behind the comedy of Roy Wood Jr. More than just a humorous hour, the conversation is an exploration of legacy, authentic leadership, and using humor as a tool for healing, community, and truth-telling. Roy shares formative moments from his upbringing, early mistakes, and the foundational “because” that drives his work—especially as outlined in his new book, The Man of Many Fathers. The discussion is raw, insightful, funny, and inspiring—a masterclass on why laughter can be a powerful legacy.

Key Discussion Points & Insights

1. Mutual Inspiration and Representation

• Mick opens by crediting Roy as a generational blueprint, stating that growing up, there were few public figures that looked like them to set an example.
• Roy credits his inspirations, notably Ricky Smiley, affirming the importance of seeing someone “like you” succeed.

  “I saw Ricky Smiley on TV in the late 90s... He put Birmingham on his back. When I saw that… I can do it from the west side. Whatever debate or doubts I had about whether or not I belonged in entertainment, gone.”
  – Roy Wood Jr. (04:13)

2. Digging Deeper: Discovering Your “Because”

• Mick differentiates between “why” and “because”—the former being the surface motivator (family, legacy), the latter being the foundational drive.

  “If I were to say, Roy, what's your why? You're going to tell me your son… But when I say, why is your son your why? I call that your because.”
  – Mick Huntoon (05:36)

• Roy’s “because” is to affirm to Black people that they aren’t alone or “crazy” for what they see and feel in America and to open the eyes of others to that reality—all through the lens of comedy.

  “If I can confirm to Black folks what they thinking and feeling while opening new eyes from non Black people on what we're going through, then mission accomplished.”
  – Roy Wood Jr. (06:00)

3. Origin Story – Creating His Own Opportunities

Roy candidly recounts his troubled college years at FAMU, including getting suspended and placed on probation for credit card theft. Unable to participate in many campus activities, he was forced to seek a radio internship off-campus—eventually talking his way into an early morning news spot at WVHT Hot 105.7.

“Negro, I had to graduate. The hell you mean?... I don't give a damn about nobody else.“
– Roy Wood Jr. (07:47)

• His hands-on radio education provided the skills and network that later propelled his stand-up and radio careers.

  “I watched [the hosts] for two hours... It was man, it was on some Star Wars Luke going to see Yoda... I really learned the craft of radio inside out from that building.”
  – Roy Wood Jr. (20:23)

4. Crafting Story and Emotion in Comedy

• Mick highlights Roy as a master storyteller, able to blend humor with emotion and never rush the narrative.
• Roy shares that his growth into a more vulnerable storyteller began during his 2021 special, Imperfect Messenger, using painful real-life experiences to elevate his material.

  “That joke was the genesis point of me going, oh, pain is a tool. Sorrow can also be woven into this fabric of what you're presenting.”
  – Roy Wood Jr. (24:50)

• He notes the influence of other comics (like Ali Siddiq) and acknowledges the delicate balance between manipulating audience emotions and staying authentic.

5. Dorm Room Fame and Evolving Beyond “Prank Call Guy”

• Mick recounts how Roy’s prank call CDs were legends among Gen Z and millennials—highlighting authentic generational comedy handoffs.
• Roy deliberately made his prank calls harder to find, focusing on evolving as a performer and not being pigeonholed.

  "If I'm not careful, [prank calls] will be the only money I make because people won't even think of me in... other regards."
  – Roy Wood Jr. (30:12)

6. The Book: The Man of Many Fathers

• Roy’s book is a series of value-driven stories, not a chronological memoir. Losing his father at 16 led him to seek mentorship from various men; each chapter explores a lesson from a different “father.”

  “I wanted to do a deep dive into who I am and why I am who I am...leave that, you know, for my son.”
  – Roy Wood Jr. (35:59)

• The book is meant for Roy’s son to read as a teenager:

  “He can pick this book up like, I don't know, maybe high school graduation...13, 14 is probably a pretty good crossroads.”
  – Roy Wood Jr. (37:30)

Notable Quotes & Memorable Moments

• On Self-Belief and Example:

  “You have to be a little crazy to bet on yourself. That’s inherent. But I think the belief that, ‘oh I could do this,’ that didn’t come from me.”
  – Roy Wood Jr. (04:15)

• On the Power of Representation:

  “If leadership is about vision, then this is what modern leadership looks like—courageous clarity and a belief that progress is possible.”
  – Mick Huntoon (02:00)

• On Channeling Pain Into Art:

  “Pain is a tool. Sorrow can also be woven... I always thought sorrow was for a one man show...No, you could probably do this and make it work.”
  – Roy Wood Jr. (24:50)

• On Legacy:

  “The written word will always have worth. They put words on walls in caves. People still go read that.”
  – Roy Wood Jr. (39:05)

• On Reaching Young Audiences:

  "People from your children’s generation... they still know me as the prank call dude. But now when you find out, oh, I've done all this other stuff, well now it's set up the way I want."
  – Roy Wood Jr. (35:01)

Timestamps for Key Segments

• [03:06] – True stories of mutual inspiration between Mick and Roy
• [05:33] – Defining the “because”; Roy explains his core motivation
• [07:19] – Roy’s candid retelling of college trouble and how adversity led him to radio
• [14:15]–[16:46] – Internship story: lessons from radio, comedy, and Black media mentorship
• [22:59] – Growth as a comedic storyteller; finding courage to blend humor and pain
• [27:00] – Mick credits Roy’s timing and storytelling as influential beyond comedy
• [30:11] – Strategic career moves: moving beyond “the prank call guy”
• [35:36] – “The Man of Many Fathers”: why the book, who it’s for, and its intended legacy
• [39:05]–[39:19] – On the enduring power of the written word

Episode Flow & Takeaways

• The episode balances humor with vulnerable, real-life storytelling. Roy’s honesty about early mistakes, the need for resilience, and making amends offers hope and relatability.
• Leadership lessons are woven throughout: cultivating legacy, the importance of visible role models, being intentional about growth and change, and mentoring the next generation.
• Roy’s “because” is both social and personal: using comedy as a tool to affirm, inform, and heal—especially for Black audiences, but also to begin overdue conversations with everyone.
• Listeners are encouraged to interrogate their own ‘because’, use pain as creative fuel, and leave a legacy that outlives technology (and even trends).

Closing Call to Action

• Mick encourages listeners to support Roy’s book, buy copies for themselves and their children, and to reflect on their “because” as their superpower.
• Roy expresses gratitude for the chance to be transparent and give back, always reminding the audience that growth, humor, and community are interconnected.

Summary in a Nutshell

"The Heart Behind the Humor" with Roy Wood Jr. goes far beyond laughs, offering a powerful, moving testament to resilience, mentorship, and intentional legacy. Roy’s journey from campus probation, to radio, to standup, to bestselling author is both cautionary and inspirational—an invitation for listeners to own their pain, disrupt expectations, and use authenticity as the ultimate leadership tool.