The Breakfast Club Best Of: Nate Jackson on Mastering Crowd Work, New Netflix Special, ‘The Office’ Spinoff, Gary Owen + More

Airdate: December 30, 2025
Podcast: The Breakfast Club | iHeartPodcasts
Hosts: Charlamagne Tha God, Jess Hilarious, DJ Envy
Guest: Nate Jackson

Episode Overview

This best-of episode spotlights comedian Nate Jackson, highlighting his journey from crowd warm-up to Netflix special, his rise in the comedy scene, crowd work mastery, opening Super Funny Comedy Club, social media strategies, his part in ‘The Office’ universe spinoff, and professional and personal insights. The hosts delve into the changing comedy landscape, creative risks, and Black entrepreneurship, while also getting candid and comedic about the industry’s evolving standards.

Key Discussion Points & Insights

Nate Jackson’s Introduction and Rise

• Who is Nate Jackson?

  • “I guess TI Dubbed me the king of crowd work. I’m an entrepreneur, I own the biggest black owned comedy club in the country.” (05:26, Nate Jackson)
  • Built Tacoma’s Super Funny Comedy Club (2021) from the ground up during COVID with no government assistance, now thriving in a prime location.

• Early Hustle and Career Longevity

  • More than two decades in comedy: “I’ve been... at it for a minute.” (07:11, Nate Jackson)
  • Started with crowd warm-up jobs and grinding in the Pacific Northwest.
  • “I was the little guy, man. I came up under Wendy and I grinded. I got it out the mud.” (08:13, Nate Jackson)

Mastery of Crowd Work

• Defining “Crowd Work” and Reputation

  • TI dubbed him "the king of crowd work."
  • “That’s what the crowd work is. You’re writing on the spot, so just switch it up.” (11:45, Nate Jackson)
  • Recalls working Hip Hop Squares, yearning for an on-screen spot while being told, “entertain the crowd. Which is mad humbling.” (07:44, Nate Jackson)
  • Hosts compare comics who rely on crowd work to “lazy” — to which Nate rebuffs: “Let me see what you doing...I see why you think it’s lazy, but I put the work.” (45:46, Nate Jackson)

• Notable Crowd Work Moments

  • Big Mac security roast: “You was like, get mad at me. I’m not the one who fed you.” (15:55, Charlamagne/Nate Jackson)
  • Risks: “It’s risky doing crowd work…that was $246,000. And I’m gonna go up and I don’t know what I’m gonna say, but…” (29:07, Nate Jackson)

• Handling the Room

  • Created the “Roast Zone” at his shows—front rows pay for the chance to get roasted. “They’d be mad if I don’t get ‘em.” (48:36, Nate Jackson)
  • Hasn’t had a real confrontation due to reading body language and crowd vibe:
    • “90% of it is reading body language…now I should never have to deal with it.” (48:36, Nate Jackson)

Navigating Sensitive Topics & Cancel Culture

• Navigating Offense and Boundaries

  • "At a point, people are like, I don’t even care what he's talking about no more… I want everybody to laugh first." (12:07, Nate Jackson)
  • “If you are gonna say anything that’s gonna be even a little bit controversy, it has to be funny.” (13:49, Co-host/Charlamagne/ Nate)
  • “I think we’re shifting back some... people like Schultz and people like Chappelle... comedy first, then we’ll talk about what’s next.” (13:06, Nate Jackson)

• Jokes on Real Life & Community

  • Discusses weight loss journey candidly and incorporates it into new material: “It was more about weight loss jokes and temptation, and you could have that at any weight.” (11:45, Nate Jackson)
  • Stays away from divisive politics, focuses on universal laughter and love.

Netflix Special: “Super Funny” (and Beyond)

• How the Special Happened

  • Built brand via social and crowd work; Netflix came via a licensing deal: “They didn’t know it was (going to be) all crowd work... If the person has 19 hours of it... okay, all right.” (30:47, Nate Jackson)
  • Intended for his mother to watch in comfort:

    “My mama getting older ... Netflix came on their old ass smart TV...this is how my mama’s gonna see me and be comfortable.” (31:46, Nate Jackson)

• Standout Special Moments

  • “Do you remember when you called that couple Seal and Heidi?” (31:16, Charlamagne)
  • “Sometimes God just give you one.” (31:19, Nate Jackson)

• Results and Impact

  • “It did massive... I’m getting stopped by people in airports, and that was happening before. So I’m trying to gauge, like, so where you see me from?” (27:38, Nate Jackson)

Social Media & The New Comedy Era

• Strategy and Reluctance

  • Initially resisted but learned the power of TikTok and YouTube: “I’m exhausted right now. I’m not getting another app... But (crowd work) started to catch.” (23:48, Nate Jackson)
  • Now at 4.5M+ TikTok followers: “It jumped for me, like from zero to 25,000 in, like, a month.” (25:03, Nate Jackson)

• Crowd Work Clips: The New Algorithm Gold

  • “Anybody watching your stream ... can make a 60 second clip... you want the clips—YouTube, Facebook, Instagram...” (58:25–58:43, Nate Jackson)
  • Observes how IRL clips drive engagement far more than traditional sketches or long-form.

Collaboration, Gary Owen + Podcasting

• Gary Owen Collaboration

  • They co-hosted “Gary and Nate” podcast—now ending due to scheduling.
  • Gently jokes about Gary “taking his style” on crowd work: “Good for Gary, man, I love that he’s getting traction because Gary’s hella funny.” (41:13, Nate Jackson)

• Professional Generosity

  • “It’s my nature to want to see those around me do well ... but they would get on and then everybody got amnesia.” (39:09, Nate Jackson)
  • Calls for more collaboration and credit in the industry.

“The Office” Spinoff: “The Papers”

• Role and Production
  • Nate plays a prominent part in “The Papers,” set in “The Office” universe—launching September 4.
  • “I wouldn’t necessarily call it a spinoff … but some of the characters are the same and there’s a serious NDA.” (50:07, Nate Jackson)
  • Praises Greg Daniels and the meticulous writing/comedy process: “They take every moment and ... manicure it to be as funny as it can be, even though it’s as dry. But it’s hilarious.” (52:54, Nate Jackson)

Black Business & Comedy Clubs

• Ownership Advocacy
  • Calls for more Black-owned comedy clubs; only three major ones exist.
  • “Why doesn't Martin have Wanda's? ... Why isn’t there a Kevin Hart comedy club? ... It makes no sense that we don’t have more brick and mortars.” (60:41–61:51, Nate Jackson)
  • Cites examples: Joe Rogan’s “Mothership,” Dave Chappelle’s club—calls for “85 Comedy Clubs.”
  • “Let’s expand and grow our industry because the people want to come to shows and then you control the buck, you control the dollar.” (62:00, Nate Jackson)

Notable Quotes & Memorable Moments (with Timestamps)

• On Weight Loss and Comedy:

  • “I want to see where my dick connect to my body.” (10:44, Nate Jackson)

• On Getting Out the Mud in Comedy:

  • “I’m your excited, huggable gangster cousin.” (05:33, Nate Jackson)

• On Sensitivity vs. Funny:

  • “If you are gonna say anything that’s gonna be even a little bit controversy, it has to be funny.” (13:49, Co-host)

• On the Value of Crowd Work:

  • “Let me see what you doing. I see why you think it’s lazy, but I put the work…” (45:46, Nate Jackson)

• On Building for His Mom:

  • “This is how my mama’s gonna see me and be comfortable.” (31:46, Nate Jackson)

• On Comedy Ownership:

  • “Let’s get to 85 comedy clubs... control the buck, control the dollar.” (62:00, Nate Jackson)

• On Leaving a Legacy:

  • “The entertainers that are watching, man, what’s up? Open something. Let’s get some comedy back on regular TV … you deserve to laugh, so do it.” (63:33–63:59, Nate Jackson)

Additional Important Segments & Timestamps

• Nate’s Hip-Hop Squares Experience (07:14–09:25)
• Weight Loss & Health Motivation (09:58–11:27)
• TikTok and Social Media Growth (23:47–26:11)
• Podcast with Gary Owen, Collaboration and Falling Out (39:09–44:13)
• Crowd Work Hosting Techniques & “Roast Zone” (48:36–49:35)
• Show Business Insights – “The Papers,” “Good Fortune” Movie (50:04–64:55)

Final Thoughts and What Nate Wants New Fans to Know

• On His Impact and Hopes for New Audiences:
  • “I got a new top five. ... Basketball got new stars … I would like to see some of the OG black comics ... reach back and create opportunities.” (60:24–61:32, Nate Jackson)
  • “Live your life to the fullest, you know? … You deserve to laugh. So do it.” (63:34, Nate Jackson)

Find Nate Jackson

• Website: NateJacksonComedy.com
• Instagram: @MrNateJackson
• TikTok: NateJacksonComedy

Episode Note:
A lively, honest, and inspiring conversation about mastery, innovation, and resilience in modern comedy, with a generous helping of jokes, realness, and business wisdom.