The Breakfast Club – "A Very Serious Interview With Donnell Rawlings"
September 3, 2025 | Hosts: DJ Envy, Jess Hilarious, Charlamagne Tha God | Guest: Donnell Rawlings

Episode Overview

This episode features comedian Donnell Rawlings, known for his raw authenticity and unfiltered humor. The discussion explores Donnell’s personal journey, co-parenting struggles, legacy in comedy, the evolving landscape of stand-up, and the tension between being funny and being taken seriously. The conversation is lively, humorous, and, at times, deeply introspective, revealing sides of Donnell beyond his stand-up persona.

Key Discussion Points & Insights

1. Co-Parenting and Personal Growth

• Therapy Experiences: Donnell shares his attempts at therapy, especially surrounding the challenges of co-parenting.
  • “It’s tough. Especially when you…you still may have some emotions involved.” (07:10, Donnell)
  • He humorously blames Charlamagne for a bad therapist recommendation that didn't resolve his issues.
  • Memorable moment: Donnell explains trying to apply on-stage strategies to real-life relationship struggles—to little effect.
• Reflections on Co-Parenting: Donnell expresses pride in creating a unified co-parenting environment for his son.
  • “My son…whenever he talks, he speaks on us as a family, as parents. It’s not like ‘I’m going to my mother’s house or my father’s house.’ We’re doing a good job with that.” (09:45, Donnell)
• Emotional Honesty: Though adamantly claiming he has no lingering emotions with his son's mother, the hosts probe and tease about unresolved feelings.

2. Comedy, Authenticity, and Public Perception

• Personal Life On Stage: Donnell discusses his policy of keeping his comedy rooted in truth.
  • “Anything I say is really what happened in my life. So that’s that.” (29:32, Donnell)
• Notoriety and Recognition: Donnell confronts the recurring theme that, despite influencing many, he is often under-credited.
  • “It happens sometimes. Sometimes people say thank you. A lot of times they don’t.” (119:10, Donnell)
• Industry Challenges: Donnell shares that being “too real” hasn’t cost him in Hollywood, but navigating perceptions as a serious person versus a comic is tricky.
  • “As a comedian, I don’t want people to take me that serious. I want people to, you know, think I’m funny and laugh at the jokes.” (46:05, Donnell)

3. Industry & Evolution of Comedy

• Rise of Social Media Comics: The panel debates how social media has transformed stand-up, with Donnell pushing back on the idea that it waters down the art:
  • “Comedy is evolving. The definition...has changed and it’s evolved.” (106:35, Donnell)
• Comedian Labels & Generational Shifts: Insightful distinctions between stand-up comedians, sketch comics, and how new comedians earn respect.

4. Masculinity, Stereotypes & Sexuality in Comedy

• Stereotypes: Open discussion about stereotypes faced by Black men in comedy and speculation on sexuality.
  • “Black men...are just for the most part, naturally homophobic. But now we live—” (131:18, Donnell)
  • Charlamagne quickly pushes back: “Don’t generalize all Black men like that!” (131:25, Charlamagne)
• Self-Acceptance and Comfort: Donnell and the hosts banter about being at ease with their identities, and how comedic freedom sometimes invites “wild assumptions”.

5. Personal Legacy, Motivation, and Giving Back

• Legacy versus Chasing Checks: Donnell is candid about being motivated by both legacy and financial security.
  • “I’m always going to chase checks…I don’t know what my legacy will be.” (99:41, Donnell)
• Mentorship: Donnell acknowledges his role in helping younger comedians, despite not always getting public recognition.
  • Jess Hilarious thanks Donnell for mentoring and advice early in her career (121:18–122:15).

6. Notable Comedy & Media Moments

• Iconic ‘Spider-Man 2’ Cameo: Donnell recounts his famous improv line in "Spider-Man 2," how a chance setback led to the opportunity, and the oddly enduring fame attached to a fleeting moment.
  • “It’s funny how one situation got shut down and it opened up...I go down the history of being a part of that brand and I had one line.” (75:40, Donnell)
• Gift Exchange: Donnell gifts personalized sneakers to the hosts, which becomes both a thoughtful and comic moment. (34:35)

7. Handling Criticism & Social Media Trolls

• Sensitivity to Criticism: Though Donnell claims not to care, he admits the difficulty of ignoring negative comments, especially on social media.
  • “It’s hard not to give a fuck. So you do care. I’m getting a little stronger with that.” (100:39, Donnell)
• Therapy and Unpacking: The recurring joke is Donnell’s resistance to “unpacking” everything in therapy, despite the hosts’ insistence.

8. Mentoring, Collaborations & The Collective

• The ‘Raw Edge Collective’: Donnell explains his initiative to support and create opportunities for up-and-coming talents through retreats, creative workshops, and collaboration.
  • “We have a group of people, and I’m gonna start this thing. It’s a raw edge collective where we...create content and we pretty much hit all type of areas in this business.” (125:47, Donnell)
• Testimonial: J. Roberts (“Javante”) is introduced; she recounts her history with Donnell and how he encouraged her at the start of her comedy journey.

9. Reflections: Mistakes and Growth

• Biggest Career Mistake: Donnell playfully claims his biggest mistake was ever appearing on The Breakfast Club, joking about the chaos and exposure it brings.
  • “First time I ever came on this show...It’s created a monster. I gotta come up here, I gotta look at you. I gotta worry about unpacking shit with this nigga over here.” (111:30)
• Lessons for His Son: Donnell wants his son to learn the importance of trying to make people feel good.
  • “If your son watches your career years from now, what’s the lesson you want him to take away? That his dad tried everything to make people feel good about themselves.” (56:42)

Notable Quotes & Memorable Moments

• On Therapy Fails:
  “Thank you for giving me the worst therapist in the world today.” (04:01, Donnell)
• On Family Bonds:
  “There’s a certain amount of love and respect I always have...” (12:30, Donnell)
• On Realness:
  “I don’t really care about what people like. If I’m presenting myself the best way I can...I can’t care about people.” (25:04, Donnell)
• On Black Masculinity in Comedy:
  “At some point you gotta be like, who gives a...and you just keep it moving.” (133:40, Donnell)
• On Mentoring Jess Hilarious:
  “The thing that fucks me up the most is...if you don’t respect anything about you respect your hustle.” (122:40)
• On Motivation:
  “I still enjoy what I do...When I do a show and people come up to me...that’s what kind of gives me motivated to do it.” (98:25, Donnell)

Timestamps for Key Topics

• Co-parenting & Therapy: 02:30–19:45
• Comedy and Public Perception: 25:00–46:00
• Comedy Evolution (Social Media Comics): 105:30–111:15
• Spider-Man 2 Anecdote: 75:30–79:40
• Handling Criticism/Social Media: 99:40–102:50
• Mentorship & Legacy: 119:00–122:30
• Raw Edge Collective & J. Roberts: 125:30–136:00
• Biggest Mistake/Joke: 111:30
• Lessons to Son: 56:40
• Closing Reflections: 145:00–end

Tone & Delivery

The episode is energetic, raw, and peppered with humor, as expected with Donnell Rawlings at the center. Jess and Charlamagne keep the pressure on with probing, irreverent questions, leading to moments of vulnerability wrapped in comedy. The dynamic is playful but occasionally veers into introspection, especially regarding Donnell’s family history and legacy.

Conclusion

Donnell Rawlings delivers a characteristically real, multifaceted interview—juggling humor, personal growth, industry insights, and social commentary. Whether discussing therapy, fatherhood, industry challenges, or the art of comedy itself, the episode affirms Donnell as a generous, self-aware force in comedy who continues to influence, evolve, and entertain.