The Breakfast Club "Best Of": Ali Siddiq, Nate Jackson, and Gary Owen Interview

Podcast: The Breakfast Club (iHeartPodcasts)
Date: December 30, 2025
Hosts: DJ Envy, Jess Hilarious, Charlamagne Tha God
Featured Guests: Ali Siddiq, Nate Jackson, Gary Owen

Episode Overview

This special "Best Of" edition of The Breakfast Club is a comedic celebration, spotlighting interviews with some of the brightest standup talents: Ali Siddiq, Nate Jackson, and Gary Owen. In an extended, free-flowing conversation, the hosts and guests reflect on the grind—from hustling on the comedy circuit and going independent, to viral crowd work clips, Netflix specials, and the real-life ups and downs that inform their material. All delivered with the signature mix of raw honesty and relentless jokes that defines The Breakfast Club.

Key Discussion Points & Insights

The Art and Journey of Comedy

• Independence in Comedy (Ali Siddiq) [12:12–21:26]

  • Ali Siddiq discusses his unique route—dropping standup specials independently "like Lil Wayne dropping mixtapes."
  • He credits Houston, his hometown, as the "capital of independent" art, championing the do-it-yourself spirit of coming up without label backing.
  • On being known for personal storytelling, Ali shares:

    “The funniest you're gonna ever be in life is based on how honest you want to be.” — DL Hughley told Ali [20:10]

  • He reveals how prison shaped his worldview and jokes, contrasting "jail" and "prison" in Black communities.
  • Memorable anecdote: Ali’s first set after being released from prison bombed hard—he got booed offstage. But he came back, adapted, and ultimately became the host at that very club.

• Crafting a Standup Special and Series [29:30–34:42]

  • Ali's "Domino Effect" special started as a one-off, but fans demanded to know “what happened next,” turning it into a series. By the third special, he was detailing how he actually got incarcerated, bringing an unprecedented honesty to the genre.
  • Strategic timing: Each part of the series dropped on Mother's Day or Father's Day, with the latest "Domino Effect Four" coming out Father's Day and running two hours.

• Crowd Work and Club Building (Nate Jackson) [40:39–49:28]

  • Nate Jackson introduces himself as an entrepreneur and comic, dubbed "the king of crowd work" by T.I., and owner of the largest Black-owned comedy club in the U.S. – Super Funny Comedy Club in Tacoma, Washington.
  • Surviving the pandemic: Nate discusses building his club just as COVID hit, forcing a grind with no external help, and eventually thriving at their new downtown location.
  • He has been in comedy for over 23 years and describes getting his break through persistence in L.A., cold calls, and hard-won crowd work gigs.

• Changing Landscape and Cancel Culture [47:46–49:28]

  • Nate addresses how the climate for comedians has shifted—more sensitivity, potential cancellation, and how social topics are "so magnetized."
  • He expresses hope there’s a swing back to letting funny be funny, referencing contemporaries like Chappelle and Andrew Schulz who push back on restrictions:

    “If you are gonna say anything that's gonna be even a little bit controversial, it has to be funny.” — DJ Envy [49:28]

Comedy Business & Viral Moments

• Netflix vs. Independence [34:01–34:50, 62:44–63:46]

  • Ali and Nate both address the allure and drawbacks of Netflix specials. Ali likes creative control and the integrity of independent work, but jokes about not turning down $20 million:

    "If they come, they come with $20 million and say, ‘Hey, man…’”—Charlamagne Tha God [34:01]

  • Nate, meanwhile, highlights the importance of accessibility for his family—his Netflix special wasn't just about reach, but so his mother could see it easily:

    “This is how my mama gonna see me and become…in the living room being like, my baby did it.” [63:16]

• Crowd Work Influence—Nate Jackson & Gary Owen [65:06–67:51]

  • Nate reveals some friction with Gary Owen over Gary adopting similar crowd work editing styles and content release rhythms—though he shrugs it off as part of the game:

    “Sometimes people come up and they're like, ‘That's the sauce.’ … There's nothing you can do.” —Nate Jackson [67:14]

  • Gary acknowledges adopting new strategies and thanks Nate for the influence:

    “Yeah. Thanks to Nate Jackson. I saw him here last week.” [86:35]

• Gary Owen’s Personal Life & Comedy [85:44–97:10]

  • A major segment is devoted to Gary Owen's family update: the accidental rift with his children after divorce, his reconnection with his son, and ongoing hope to reconnect with his daughter.
  • Gary and the hosts banter about handling serious topics through jokes and how his son has a similarly dark sense of humor, creating room for healing.
  • Transparent advice about divorce:

    “Get to a point where you’re cordial with your ex, and you guys decide what you want to do. …These lawyers are playing us…they will literally find one thing to keep it going.” —Gary Owen [95:13]

Noteworthy Quotes & Memorable Moments

• On Comedy Comebacks:

  "So I end up becoming the host of that same place that I got booed in…Just Joking Comedy Cafe." —Ali Siddiq [20:05]

• On the Hard Beginnings:

  "I used to juggle 10 different logins and apps. Now one platform I manage my store, sell online, sell on social, even tag products right from my phone…" —Lauren LaRosa on managing her business with Shopify [21:29]

• On Joke Sensitivity:

  “‘Depending on the word…but…you gotta be so funny to the point where they don’t even wanna cancel you.’” —Nate Jackson [54:20]

• On Family Reconciliation:

  “The first thing he said was, ‘Dude, I know we got a lot to work on…But I really need your help with this problem right now.’ So I went into immediate, like, dad mode.” —Gary Owen, on reconnecting with his son [91:27]

Timestamps for Key Segments

• [12:12–21:26] – Ali Siddiq: The struggle, independence, and becoming a storyteller.
• [29:30–34:42] – The making and expansion of "Domino Effect" specials.
• [40:39–49:28] – Nate Jackson: Super Funny Club, crowd work, COVID, and Netflix.
• [54:20–58:07] – Nate on joke boundaries, crowd work controversy, and lessons from Montreal.
• [62:44–63:46] – Nate explains choosing Netflix for his mom.
• [65:06–68:06] – Nate and Gary Owen on editing style dispute and podcast joint venture.
• [85:44–97:43] – Gary Owen: Handling grief, family drama, healing after divorce, and selling out shows.

The Breakfast Club Flow & Tone

• Balanced between brutally honest and consistently hilarious—no one is safe from roasting, including the hosts themselves.
• Real-life stories about struggle, career pivots, and family drama are interwoven with lively banter and sharp one-liners.
• The hosts—Envy, Jess, and Charlamagne—mix appreciation with playful antagonism, keeping the conversation high energy and unfiltered throughout.

Conclusion & Final Takeaways

This “Best Of” episode offers listeners a rollercoaster of laughs, life stories, and real talk straight from standup’s front lines. From the long arcs of Ali Siddiq’s life fueling his specials, to Nate Jackson’s rise via relentless hustle and crowd work mastery, to Gary Owen’s vulnerable updates on family and the ever-evolving business side of comedy—each segment is packed with insight and authenticity. Underneath the jokes, there’s a core message: Comedy is not just about laughs, but about honesty, perseverance, and connection.
“Self accountability is trusting yourself to be there for you, because the only person you are destined to become is the person you decide to be.” —Charlamagne Tha God [98:16]

Where to Follow & Support the Guests

• Ali Siddiq: @alisiddiq (Instagram), YouTube (“Ali Sidiq Comedy”), new specials “Domino Effect” series.
• Nate Jackson: natejacksoncomedy.com, @mrnatejackson, Netflix special “Super Funny.”
• Gary Owen: @garyowencomedy, touring nationwide, various podcast projects.

This summary captures the highlights and spirit of the episode for those who missed the show—and for fans eager to revisit the best laughs and wisdom from today’s most compelling comics.