Good One with Jesse David Fox

Episode: "Bob the Drag Queen Knows She's Funnier than Madonna"
Date: February 19, 2026

Episode Overview

This episode features comedian, Broadway performer, and drag superstar Bob the Drag Queen in conversation with host Jesse David Fox. The discussion centers on Bob's multi-faceted career—ranging from their celebrated run on RuPaul's Drag Race, to stand-up comedy, a new Hulu special ("This is Wild"), co-hosting podcasts, a stint on The Traitors, and opening for Madonna. Together, Jesse and Bob explore what it means to be a drag queen today, the evolution of drag in popular culture, and how Bob continues to redefine expectations—often with humor, candor, and a sharp confrontational wit. The conversation also delves into Bob’s creative processes, confrontational humor, personal losses, and aspirations, all while maintaining the show's signature mix of serious insight and genuine laughs.

Key Discussion Points & Insights

Life as a Broadway Star & Routine Mishaps

• Bob is currently starring in Moulin Rouge on Broadway, which means an intense, regimented schedule: “I'm doing eight shows a week on Broadway.” (02:23)
• Bob recounts a recent, sitcom-worthy mishap involving getting locked out of a gym locker, forced to interact with a disliked doorman while dressed in "the sluttiest little, like, gay boy gym shorts," sparking a comedic observation: “It's not a tank, it's a skank tank.” (03:11)
  • Memorable Moment: Feeling the situation would play well as a "Curb Your Enthusiasm" bit. (04:47)

Broadway: Long-Term Ambition & Arrival

• Bob reflects on coming to NYC in 2008 with Broadway aspirations, taking 17 years to reach that goal, and feeling the achievement is both overdue and exactly right: “I feel like I should have been on Broadway years ago. I'm shocked it took this long, quite frankly.” (05:50)

The Evolution of Drag & Drag Race’s Impact

• Bob discusses what drag meant when starting 17 years ago—counterculture, limited visibility even for icons like RuPaul.
• Now, drag is mainstream, there are “over 100” full-time queens in NYC, and being Bob the Drag Queen is a draw in itself. (06:54)
• On Drag Race’s influence:
  • For some, it's been transformative, creating massive opportunities.
  • For others, especially those who had negative runs on TV, it’s “fucked up drag,” referencing Jasmine Masters. (08:01)
  • Notable Quote: “For me, I'm like, it's working great for me. And I acknowledge that.” (09:07)

“Growing Up” with Drag

• Contrary to common belief, Bob did not “grow up in a drag bar” owned by their mother (“I was nine”), but had indirect exposure and even early warnings: “Sidney got shot by a drag queen at the bar... don't fuck with drag queens. They're dangerous.” (09:30, 10:26)
• RuPaul’s Drag Race was Bob’s gateway to seeing drag as a career: “I could do that. That's how I've done a lot of stuff in my life. Looking at it going, I can do that.” (10:31)

Reality TV & The Anatomy of Drag Race

• Bob analyzes Drag Race as the toughest reality TV show, given the barrage of required talents—modeling, singing, sewing, acting, comedy, and social maneuvering: “You have to model, you have to sing, you have to dance, you have to act, you have to sew... This is insane.” (16:23)
• On the “meta” nature of later seasons and contestants trying to self-produce for fandom perception, often at the cost of authenticity. (11:06)

Improvisation, Comedy, and Snatch Game

• On Snatch Game, Bob describes why it’s a uniquely tough improv challenge: “Everyone doesn’t have great improv skills... My best friend is actually really bad at improv, but she's really funny.” (14:09)
• Legendary for playing two characters in Snatch Game, Bob details the last-minute decision and risk-taking: “I just snuck the Carol Channing outfit underneath my outfit... I took a big risk and I swung big.” (17:37)
• Favorite Snatch Game moments include Deja Skye’s, “I was born at a very young age,” but a reminder: “We're not watching SNL... We are watching maybe two comedians and six people who don’t know the first thing about comedy.” (15:43)

Stand-Up: From Drag Bars to Hulu Specials

• Bob’s Hulu special, This Is Wild, stands out by not pandering to drag or Drag Race fans: “The joke is not that I'm a drag queen. The joke is not that I was on reality TV... I've been doing stand-up comedy for 17 years.” (26:59)
• Many don’t know Bob is a seasoned stand-up with roots in NYC clubs—sometimes even performing out of drag, still using “Bob the Drag Queen” as the name. (28:24, 29:32)
• On being a drag queen and a stand-up: “The drag is just my work clothes. You know what I mean? The drag queen is the title, Bob's the name, and then the uniform is just what I'm wearing when I'm on stage.” (31:19)
  • Memorable exchange: On whether everything is drag: “I don't think everything's drag. I just want to be clear that what me and J.D. Vance are doing, we're not both doing the same thing.” (30:13)

Creative Motivation & Confrontational Humor

• Bob avoids crowd-pleasing, insular material, instead choosing wide-reaching subjects—religion, race, trauma.
  • Slave 4 U performance: Confrontational art blending Britney Spears with Chris Rock, forcing audience reflection: “It is very confrontational humor. I do very, very confrontational humor.” (45:42)
  • On how art like Whoopi Goldberg’s joke inspires reflection, not just guilt: “Every confrontation isn't an accusation. It's just an opportunity to reflect.” (47:09)
• When writing, Bob avoids relying too heavily on fan service: “When I started writing comedy, it wasn’t about those things. It was about my experience, my observations around me.” (44:31)

Writing, Memoir, and The Harriet Tubman Novel

• Rejects the commercial memoir path—“I wouldn't read my memoir, so I wouldn't want to write it”—and instead crafts a bold speculative novel about Harriet Tubman making a hip-hop album. (50:06)
• The impetus is to examine history, freedom, and survivor guilt through black, queer eyes, blending absurdism with deep reckonings. (51:19)

On Religion, Faith, and Identity

• Bob is open about being raised religious but now a vocal critic—especially of Christianity’s oppressive history toward Black and queer people: “I prayed every night to a religion that was chosen for me… It’s really oppressive to us.” (51:58)
• Jokes about being a queer person who doesn’t believe in astrology as social suicide among lesbians: “I can't talk to any lesbians. Why is that? Because they're serious about their fucking zodiacs.” (53:33)

Fame, The Dead Moms Special, and Personal Grief

• The Dead Moms Comedy Club—a special for/with comedians whose mothers have died—originated from Bob’s coping: “I'm one of those folks who... could not shut up about my mom being dead.” (56:12)
• Bob wanted to feature comedians with diverse relationships with their mothers, not just the stereotypical mother’s boy story.

Madonna, Creative Collaboration & Who’s Funnier?

• Opening for Madonna involved true creative input—writing for the show, creating segments, and being valued as a peer: “I gave valuable input, and she saw me as a true creator.” (65:32)
  • Memorable Story: Madonna’s competitive streak—“Bob, I’m funnier than you.”—and Bob’s response: “You're not.” Madonna wants to “go joke for joke” with Bob after the tour (66:46).
• Madonna’s unique ability to laugh at herself: “She was snorting, like, snorting with laughter...at herself being serious.” (69:03)

What is a Drag Queen’s Job?

• Responding to Michelle Visage’s claim it's “to lip sync,” Bob says: “Michelle's old. She's old... That's like being like, a man's job is to provide for his family.” Stresses drag is about entertaining in myriad forms, not just one skill. (58:21)

Notable Quotes & Moments

On Career Longevity and Ambition

• Bob: “I'm a really funny comedian. I can sing well enough. I can sew well enough. I'm a pretty good dancer. But it helps to really excel at something—or have at least a B in everything.” (16:58)

On Humor and Identity

• On Whoopi Goldberg’s Influence: “I look like Whoopi Goldberg... And growing up, hearing people... just call Whoopi Goldberg ugly... So you're watching everyone say it, and you're kind of like, whoa, this is crazy. And then as an adult, I got to go back and look at pictures of Whoopi Goldberg, and she was never ugly... I cannot believe that I let the world convince me that her and I were ugly.” (69:33)

On Drag & Mainstream Culture

• On the shift in drag culture: “It feels a lot less counterculture... Now they're interested in the fact that it is Bob the Drag Queen.” (06:54)
• On creative fulfillment: “I just really like to entertain people. Entertainment is really, truly, the most pure form of manipulation... I just want to make you feel what I want you to feel.” (59:45)

On Never Bombing

• “I have never, ever, ever bombed. I have had crowds turn on me before, but I always win them back... I've never just had crickets in the audience, ever.” (80:51)

Important Timestamps

• Opening Mishap & Doorman Story: 02:23 – 04:47
• Dreams of Broadway & Arrival: 05:01 – 05:50
• Drag’s Evolution & Drag Race Impact: 06:54 – 09:07
• Danger of Drag & Early Exposure: 09:30 – 10:26
• First Seeing Drag Race as a Career: 10:31
• Snatch Game Strategy & Improvisation: 14:09 – 19:23
• On Not Pandering in Stand-Up: 26:59 – 27:15
• Identity as Stand-Up in and out of Drag: 28:24 – 31:19
• Performative Confrontation & Social Commentary: 44:49 – 47:09
• On the Dead Moms Comedy Special: 56:12 – 57:30
• Madonna Collaboration & “Funnier than Madonna” Story: 65:32 – 66:46
• Refuting “Lip Sync” as the Drag Queen’s Job: 58:21 – 59:45
• "Never Bombed" Conversation: 80:51 – 82:35

The Laughing Round & Bonus Stories

Favorite Joke:
A long set-up involving a lobster and a clam making love on a beach, ending: “When he comes up behind me and takes one claw and puts it here, and takes his other claw and puts it here. My pearls. My pearls.” (75:28)

Legendary Comedy Encounters:

• Judah Friedlander once questioned Bob’s drag name, not knowing it would later become iconic. (76:52)
• Confronting Tracy Morgan at Caroline’s after anti-gay comments: “I had this confetti cannon... I was gonna take the confetti cannon out and just shoot him right in the face... But I chickened out...” (77:44)

Advice for Future Glitter Protestors:
“If you want to confetti someone, just so you know, shoot it above them... They will still be covered in glitter.” (79:10)

Tone & Style

The conversation is lively, sharp, and often confrontational (in Bob's signature style), but laced with warmth and humor. Jesse keeps the discussion moving with detailed, nerdy questions; Bob responds with candor, clarity, and comedic timing. Both speakers maintain a mutual respect, even as they poke fun at themselves and the culture they critique.

Takeaways for Listeners

• Bob the Drag Queen isn’t just a performer who fits into the Drag Race mold, but a boundary-pushing artist, stand-up, and writer who prioritizes authenticity and wide-ranging cultural commentary, often by making audiences uncomfortable in ways that inspire reflection.
• The realities of drag’s transition into the mainstream, and how that success brings new complexity for artists.
• How great comedy and art draw more from life and curiosity than from easily marketable in-jokes.
• The most radical thing a drag queen can do now is continue to evolve—refusing to be limited by any one format, expectation, or stereotype, whether in a bar, a Broadway stage, or collaborating with Madonna.

For more, check out Bob’s stand-up special "This Is Wild" on Hulu, and follow new projects via Bob’s official website or social media.