Podcast Summary: You Made It Weird with Pete Holmes

Guest: Wayne Brady
Date: October 2, 2024

Overview

In this deeply candid, joyful, and insightful episode, Pete Holmes sits down with the multi-talented Wayne Brady. Known for his improvisational genius and wide-ranging career, Wayne opens up about his lifelong battles with imposter syndrome, mental health, identity, family origins, his journey to accept his talents, and his recent coming out as pansexual. The discussion flows from the pressures of fame to childhood trauma, building self-worth, the evolving landscape of entertainment, and the beautiful absurdities of being alive and creative.

Key Discussion Points & Insights

1. Nerding Out Over Comics & Showbiz Hustle

• [01:32-03:43] Wayne, a self-proclaimed comic book nerd, dreams of playing Mr. Terrific in a DC adaptation and riffs with Pete on the business of producing such shows.
  • Quote: “I’m a straight up comic nerd. Like for real, for real.” – Wayne ([02:41])
• Pete laments the challenges of funding digital comedy, with Wayne offering to help produce.
• They discuss early-career milestones and the shifting sense of accomplishment in entertainment.
  • Quote: "I used to drive to San Diego from here, two hours to sing in wedding bands for $50." – Wayne ([05:50])
  • Quote: "When you give me a check for a couple thousand dollars. Are you kidding me?" – Wayne ([05:59])

2. From Whose Line to Social Media Stardom

• [06:07-11:16] The pair compare the old showbiz thrill of being on TV to today's viral fame ecosystem, from Antoine Dodson’s “Hide your kids, hide your wife” moment to TikTok stars.
  • Quote: “Someone’s first brush with social media – it’s either fame or infamy.” – Wayne ([06:44])
  • Quote: “I remember coming up, I was like, it’s the guy from Road Rules. … And now I’m like, who cares? Any bus that pulls into the bus stop, he got on it.” – Pete ([10:14])
• Wayne touches on the difference between creating in private and performing live, especially for comedy and improv.
  • Quote: “If you can’t ply your trade live, I don’t know if I have as much respect for you.” – Wayne ([11:16])

3. Pressure, Ownership, & Imposter Syndrome

• [12:13-21:14] Pete probes Wayne on the pressures of being an all-around improv virtuoso and the expectation to "perform" on cue.
• Wayne details early sidekick roles, his feeling like the "seventh guy in the back," and the evolution toward owning his skills.
  • Quote: “...the tools that I needed to develop because ... I’ve accepted that I am very, very good at this art.” – Wayne ([15:09])
• Stories of being one of few Black performers, imposter syndrome in comedy, and learning to take pride in his achievements.
  • Quote: “I couldn’t take it in. I could not accept that gift. In fact I fought it.” – Wayne ([18:47])

4. Standup, Peer Respect, & the Science of Comedy

• [21:42-24:34] The conversation turns to peer validation, explaining comedic perspective to audiences, and the “membrane” one crosses to be accepted as ‘funny.’
  • Quote: “So much of the first 10 years of comedy is like waiting for someone to say: you’re a comedian, you’re one of us.” – Pete ([21:07])
• The science vs. art of standup and improv, the grind behind crafting material, and why instant TikTok magic isn’t the same as showbiz discipline.

5. Summoning Playfulness, Rituals, and Show-Time Mindset

• [24:58-27:39] Pete asks Wayne about the practice of “summoning” his onstage persona, and if he has rituals.
• Wayne attributes his ability to perform now to gratitude for being wanted, booked, and anticipated by audiences.
  • Quote: “Isn’t it cool that there are enough people that go: we got Wayne Brady on the show ... he’s gonna kill.” – Wayne ([27:03])
  • Quote: “Gratitude being the opposite of fear. … You can’t feel afraid and grateful at the same time.” – Pete ([27:49])

6. The Terrifying Joys and Dangers of Headlining & Perfectionism

• [30:14-33:54] Wayne walks through going from the surprise delight in group improv to the demands of solo stardom; the pain and pressure of always having to "bring it," fear of not being enough, and its toll on friendships and well-being.
  • Quote: “I was miserable. I was absolutely.” – Wayne ([31:54])
  • Quote: “I’ll replay it for weeks and weeks and weeks.” – Pete ([32:18])
• They bond over letting go, with therapy helping Wayne move from obsessive control to trusting ensemble work.

7. Inner Child, Trauma Work, & Gratitude

• [34:41-39:13] The show dives deep into psychological territory: childhood wounds, the inner child as a driver for performance, and the reparative power of gratitude and awareness.
  • Quote: “When I’m on stage doing improv ... this is Lil Wayne getting a chance to play with another kid.” – Wayne ([34:56])
• Pete likens stage gratitude to “showing” his child self the present moment’s goodness.
  • Quote: “Really, there’s another way to say the same thing, which is I’m saying to my child self: look, look, look!” – Pete ([35:29])

8. Family, Generational Guilt, and Parental Dynamics

• [39:32-52:22] Wayne unpacks his upbringing—his military father’s absence, being raised by his strict grandmother, and the generational expectations around education and safety.
  • Quote: “My father was not physically around...he made the choice early on to ask my grandmother to raise me so that I’d have the same upbringing he did.” – Wayne ([39:36])
• Profound discussion about carrying dreams and anxieties for ancestors, the meaning of college in Black and immigrant families, and seeing these cycles repeat with his own daughter.
  • Quote: “So I had a lot of guilt around that, too. So I needed to succeed to prove to them that I was OK.” – Wayne ([50:52])

9. Race, Comedy, and the Wayne Brady "Blackness" Debate

• [56:08-61:39] Pete asks about the notorious "Wayne Brady makes Bryant Gumbel look like Malcolm X" joke. Wayne candidly discusses the pain, Paul Mooney’s intent, and why challenges to his racial authenticity stung so deeply.
  • Quote: “When we look at another Black person ... and we question their blackness—first of all, and I say, what is your blackness? … Who says you are the gatekeeper and the arbiter of that?” – Wayne ([59:10])
  • Wayne explains processing this in therapy and how it tapped into his lifelong desire to belong.

10. Battling Depression and Embracing Therapy

• [63:30-73:05] Wayne opens up about living with undiagnosed depression and anxiety, the hidden toll it took behind the scenes, and a turning point in seeking genuine therapy, not just "gaming" therapists.
  • Quote: “I wish I could say I started going [to therapy] a while after all that happened. Really, I didn't take therapy seriously until 10 years ago.” – Wayne ([32:40])

11. Solitude, ADHD, and Growing Up Inside

• [73:32-78:10] Both Wayne and Pete relate as "indoor cats," shaped by protective, nervous upbringings that cultivated rich inner worlds and imagination, but fueled social withdrawal as adults.
  • Quote: "The Wayne that people see on TV is drastically different ... I'm a very solitary person and developed that as a self-defense mechanism." – Wayne ([73:05])

12. Coping Mechanisms: Community, Men's Groups, Small Steps

• [78:10-88:00] Discussion of men’s groups as community, the importance of connection to combat isolation, and practical tools for coping with overwhelm and executive dysfunction (making the bed, doing just the next thing).
  • Quote: “If I make my bed, it all falls into place.” – Wayne ([86:59])
  • Quote: “Who could do the day you’re doing? Nobody, including you. But isn’t there even just a comfort ... just this, just this?” – Pete ([88:00])

13. Coming Out as Pansexual

• [89:37-98:46] Pete respectfully asks Wayne about being pansexual and the complicated, ongoing journey of self-discovery and public disclosure.
  • Quote: “I’m still figuring it out too.” – Wayne ([90:16])
  • Wayne discusses misunderstandings, people's desire to categorize, and that his “truth” is still a journey, influenced by his faith and family support.
  • Quote: “It means that you would be open to love for everyone. Hearts, not parts.” – Wayne ([97:56])

14. Faith, Meaning of Life, and Legacy

• [98:49-107:07] Wayne credits Pete’s public spiritual searching for encouraging his own. They discuss the importance of being unembarrassed about faith, separating love from fear, and following the example of elders with deep self-faith.
  • Quote: “Maybe I can… that’s how you don’t walk around mad and angry and negative, asshole sometimes…” – Wayne ([103:01])
  • Quote: “When you know yourself to be a child of God, you know you’re going to your father. … Don’t be afraid of yourself.” – Pete ([105:39])
  • They tie loving oneself to being able to build and contribute rather than be cynical and destructive.

15. The Funniest Moment Ever

• [107:21-109:48] In a closing segment, Pete asks Wayne about the hardest he’s ever laughed. Wayne recalls being on stage in pure flow with his best friend Jonathan, laughing until he, literally, farted:
  • Quote: “That’s when I’ve laughed the hardest… laughing so hard onstage that I just ripped one.” – Wayne ([109:15])

Notable Quotes & Moments (with Timestamps)

• Wayne on gratitude as fuel: "I can operate at a level of gratitude that I wasn’t capable of before, and that unlocks it for me." ([26:05])
• Wayne on feeling singled out: "I felt like there was no seat at the table for me." ([61:39])
• Pete on inner child work: "Really… I’m saying to my child self: look, look, look!" ([35:29])
• Wayne on imposter syndrome in success: "You don’t get a laminated comedy ID, you know what I mean?" ([20:54])
• Wayne on therapy and men’s group: "Being a part of a men's group gave me a community of at least a couple guys who I could talk to…" ([78:10])
• Pete on pansexuality and gender boxes: "When what you’re saying is life, the human experience… is so much stranger and wilder and mysterious and unknowable." ([92:14])
• Wayne on coming out: "That’s part of the journey for me. So I’m still trying to find out exactly what it means." ([98:46])
• Wayne on faith and self-love: "Well, if you’re saying that you’ve got faith and you love him, then you gotta love you." ([105:39])
• Wayne on laughter and joy: "I've laughed so hard on stage with Jonathan that I just ripped one." ([109:15])

Important Timestamps

• Comic Nerd/Dream Roles: [01:32-03:43]
• Old Showbiz vs. Viral Fame: [06:07-11:16]
• Imposter Syndrome, Early Career: [15:14-21:14]
• Gatekeeping, Blackness, & Chappelle show joke: [56:08-61:39]
• Therapy & Depression: [63:30-73:05]
• Childhood Solitude & Imagination: [73:32-78:10]
• Practical coping (making the bed): [84:03-86:59]
• Wayne on coming out as pansexual: [89:49-98:46]
• Meaning of Life & Faith: [98:49-107:07]
• Hardest Laughter: [107:21-109:48]

Concluding Thoughts

Wayne Brady and Pete Holmes co-create a conversation that moves seamlessly between deeply funny and refreshingly honest. From the challenges of living up to industry and community expectations, through inner battles with self-worth and depression, to moments of acceptance (creatively, racially, sexually, and spiritually), this episode is a celebration of vulnerability, resilience, and joy—their shared "weirdness" is rendered not just relatable, but healing.

Memorable Sign-Off:
"I like how to make a up!" – Pete ([110:12]), after Wayne recounts laughing so hard he ‘ripped one’ onstage.

Check Out:

• Wayne Brady: The Family Remix (Hulu / Freeform)
• Let’s Make a Deal (CBS)
• Whose Line Is It Anyway? (CW)

Wayne’s Final Words:
"Keep it crispy, baby." ([111:19])

This summary covers core topics, highlights the episode’s wisdom and hilarity, and respects the conversational spirit and candor that Pete and Wayne brought to the mics.