Podcast Summary: The Dan Le Batard Show with Stugotz – South Beach Sessions featuring Deon Cole

Release Date: August 14, 2025

1. Introduction and Early Struggles ([02:33] - [09:04])

The episode begins with Dan welcoming comedian Deon Cole to the “South Beach Sessions.” Dan highlights Deon’s diverse background in Hollywood, including his roles in popular TV shows like Black-ish and Grown-ish, his stand-up comedy, and his work as a writer and producer for Conan O'Brien.

Dan: "This man right here, Deon Cole, he is thirsty. Look at that. He is starting. He is ready for everything here." ([02:33])

Deon Cole expresses gratitude for being on the show, thanking Dan and the platform for the opportunity.

Deon Cole: "For us here and thank you so much for having me, man. Sharing your platform." ([03:02])

2. Comedy as Therapy ([03:06] - [04:18])

Dan probes into Deon’s passion for stand-up comedy, asking which aspect of his multifaceted career he enjoys the most. Deon reveals that stand-up is particularly therapeutic for him.

Deon Cole: "I think stand up because it's more therapeutic, more personal. You know, it's more my thoughts and. Yeah, it's. It's more me." ([03:13])

When pressed about the therapeutic nature of comedy, Deon elaborates on how performing stand-up allows him to express and cleanse his thoughts in a way that feels communal, likening it to an AA meeting.

Deon Cole: "It does become therapeutic because it's like, oh, we all like an AA meeting in a sense. You know, it's similar to that." ([04:18])

3. Creating a Stand-up Special on His Mother’s Passing ([04:18] - [07:53])

Dan brings up Deon’s notable stand-up special centered on the passing of his mother, a deeply personal and uncommon subject in comedy. Deon recounts the emotional turmoil of shooting the special on the anniversary of his mother’s death.

Deon Cole: "I could hear her almost like, saying, do it. We got you. I got you." ([06:12])

He describes feeling his mother’s presence during the performance, which provided him with strength but also led to intense emotional moments post-show.

Deon Cole: "I could feel her warmth, man. And I could feel her going, stop cursing so much." ([07:14])

4. Growing Up in Chicago and Facing Racism ([08:11] - [17:22])

Deon shares memories of his childhood in Chicago, emphasizing the love and humble beginnings despite financial hardships.

Deon Cole: "Lots of love. Plenty love, man. I never. We were like. I mean, like every other story that has been told." ([08:21])

He details the transition from a gang-infested area in Chicago to a predominantly white suburb in Dalton, Illinois, where he encountered overt racism, including physical confrontations and hate crimes.

Deon Cole: "Damn. But my mother moved me from there, moved me to the suburbs." ([12:44])

Deon describes the constant fear and necessity to defend himself, leading to the formation of a close-knit group with other black youths who supported each other.

Deon Cole: "It was this pack of us, you know, which is my best friends to this day." ([14:39])

5. Discovering Comedy as a Path ([17:22] - [29:06])

At 22, motivated by a bet from his friend Gwil and facing repeated rejections from comedy clubs, Deon embarks on his stand-up journey. Despite initial struggles, including being banned from multiple venues, he perseveres.

Deon Cole: "I went up and bombed on the tour. I think I did like two, three dates out of like a 20 city deal." ([29:15])

This phase becomes a turning point as Deon transitions from performing stand-up to focusing on writing, eventually catching the attention of other comedians and landing writing gigs.

Deon Cole: "After that, I just wouldn't leave the house because everyone thought I was gone for three weeks." ([32:13])

6. Writing for Conan O'Brien ([32:39] - [35:07])

Deon narrates how his dedication to writing led him to write for Conan O'Brien after an impromptu interaction during a guest appearance.

Deon Cole: "He was like, yes, you kill it later. And I'm on a whole nother page because Conan has, like, Neil Diamond and Eddie Vedder and all these people coming through." ([58:11])

He emphasizes Conan’s innovative approach and the rigorous process of joke creation and deconstruction that influenced his own comedic style.

Deon Cole: "You have to write the joke. Then you have to write deconstructing the joke. Like, that's how it is." ([60:00])

7. Embracing the Outsider Role and Unique Comedy Style ([41:43] - [43:28])

Deon discusses his self-perception as an outsider and how it shapes his comedy. He prefers to listen and be genuinely interested in others rather than forcing humor, which sometimes leads to others perceiving him as serious or weird.

Deon Cole: "I'm all about worlds. Like, I'm interested. Like, yo, what did you do today?" ([42:51])

This unique approach fuels his comedic material, allowing him to explore diverse topics and maintain a distinct voice in the industry.

8. Future Ambitions and Perspectives on Late-Night TV ([48:07] - [53:29])

Deon shares his aspiration to host his own late-night talk show, advocating for more diversity in such platforms. He critiques the traditional format of late-night shows and expresses a desire to revamp them to reflect contemporary times and diverse perspectives.

Deon Cole: "I would love to host a late night talk show. It ain't even no black people doing it. I don't even know why." ([48:42])

He envisions a talk show that embraces different viewpoints and pushes the boundaries of conventional late-night formats.

9. Overcoming Early Career Challenges and Achieving Success ([53:29] - [62:57])

Reflecting on his journey, Deon illustrates how persistence and embracing his unique comedic style led to significant breakthroughs, including Emmy nominations and roles in major TV shows.

Deon Cole: "I'm making enough money where I'm happy." ([45:31])

He credits his manager, Kirsten, for introducing him to Hollywood and facilitating opportunities that aligned with his authentic self, despite initial setbacks and rejections.

10. Personal Life and Upcoming Projects ([62:57] - [67:50])

Deon touches upon personal experiences, including a challenging birthday that led to hospitalization, hinting at future discussions around it.

He also announces his upcoming podcast, "Funny Knowing You", aimed at introducing fellow comedians and fostering conversations akin to a talk show format.

Deon Cole: "It's gonna be a talk show almost based in a sense." ([64:56])

Additionally, he promotes his role as the lead in "Average Joe" on Netflix and BET, celebrating this milestone in his acting career.

Deon Cole: "First time as a lead man." ([67:13])

Key Takeaways

• Therapeutic Nature of Comedy: Deon Cole uses stand-up as a means to process personal trauma and connect with audiences who understand his experiences.

• Resilience in Face of Adversity: Overcoming systemic racism and personal hardships in Chicago shaped his comedic and professional journey.

• Transition from Performer to Writer: Initial struggles in stand-up led Deon to focus on writing, eventually securing a pivotal role in Conan O'Brien's show.

• Authenticity and Unique Voice: Embracing his outsider status and genuine curiosity fuels Deon's distinctive comedic style, setting him apart in the industry.

• Future Aspirations: Deon aims to innovate late-night television by introducing more diverse perspectives and plans to launch a podcast that mirrors a talk show environment.

Notable Quotes

• Deon Cole on Therapeutic Comedy:
  "It does become therapeutic because it's like, oh, we all like an AA meeting in a sense." ([04:18])

• Deon Cole Reflecting on His Mother:
  "I could feel her warmth, man. And I could feel her going, stop cursing so much." ([07:14])

• Deon Cole on Late-Night TV Diversity:
  "I would love to host a late night talk show. It ain't even no black people doing it. I don't even know why." ([48:42])

• Deon Cole on Persistence and Success:
  "I'm making enough money where I'm happy." ([45:31])

This episode of The Dan Le Batard Show with Stugotz offers an intimate look into Deon Cole's life, exploring how his experiences have shaped his unique approach to comedy and his trajectory in the entertainment industry. Through candid conversations and heartfelt reflections, listeners gain insight into the resilience and authenticity that drive Deon's success.