Sunday Sitdown with Willie Geist: Sebastian Maniscalco on His Slow-Burn Rise and Working With Robert De Niro

Date: November 22, 2025
Guest: Sebastian Maniscalco

Episode Overview

In this episode, Willie Geist sits down with comedy powerhouse Sebastian Maniscalco at New York’s iconic Gotham Comedy Club – a venue that played a formative part in Maniscalco’s rise. They explore Sebastian’s methodical, “slow-burn” career progression from grinding out sets in comedy clubs to headlining sold-out arenas, his family roots in Chicago’s Italian community, his Netflix specials (especially “Is It Me?”), and the surreal experience of having Robert De Niro portray his father in a film based on his life. The conversation is filled with intimate anecdotes, insights into the craft and business of stand-up, and laughs about family, parenting, and the ever-shifting cultural moment.

Key Discussion Points and Insights

1. Returning to Gotham Comedy Club

Nostalgic Memories:
- Sebastian recalls doing “14 shows in one week” at Gotham, which solidified it as his “home away from home in New York.”
- Fun tidbit: The comedy club was transformed into the Copacabana for the filming of The Irishman—the very scene where Maniscalco (as 'Crazy Joe Gallo') has his notable moment with Joe Pesci and Robert De Niro.
- [03:17 – 04:10]

2. The Comedy Club vs. Arena Experience

The Club as Comedy’s Gym:
- Sebastian says, “This is where comedy should be enjoyed… you’re feet away from the performer… it’s tight, everybody’s tightly packed in. For me, I love coming to a comedy club to work out some material. You kind of see what’s good, what’s not.”
- Contrasts the intimacy and experimental freedom of clubs with the heightened expectation of theaters and arenas.
- [04:24 – 05:01]

3. Creating “Is It Me?” and the Vegas/Rat Pack Vibe

Initially planned before the pandemic, the special's material was refined in LA’s Comedy Store and on the road.
On the Vegas Theme: Sebastian says,

“I wanted to do a throwback to the Rat Pack…dressed up in a tuxedo…made the set look a little 1950s, 1960s Las Vegas. I asked the audience to dress up in formal wear, which about 25 of them did.”
- Shares how his parents’ stories of old Vegas imbued the special with nostalgia, and his own desire to “fit in more back maybe with the Rat Pack than I do with people nowadays.”
- [07:51 – 09:18]

4. Mining Family for Material

Sebastian’s mother complains about not making it into the act, joking, “Where am I? People think I’m dead, you know, so my mom wants in, and my dad wants more of him.”
His father—an Italian immigrant and endless source of stories—“parlayed” his son’s success into favors and preferential treatment in Chicago (“I’ve been paying for my dad’s remodel through tickets”).
Classic “immigrant mentality” stories, e.g., his father distrusting painters’ choice of paint:

“He thinks they’re gonna put cheap paint in those buckets. What kind of mindset is this?”
[09:45 – 11:45]

5. Comedy, Cultural Critique, and PC Culture

Maniscalco doesn’t wade into politics but addresses “the environment, the culture,” poking fun at hypersensitivity and nostalgia for when comedy “was supposed to be all in good fun.”
He observes,

“As soon as you start editing your comedy and not doing what you think is funny, you might as well not be doing it because it’s not going to be enjoyable.”
- Adds, “There’s a small portion of society that gets bent out of shape, and those people tend to be the loudest voices.”
- He strives to put his audience at ease, often warning when a bit might “bend them out of shape,” which helps everyone relax.
- [12:29 – 16:04]

6. Origins: Chicago, Family Dinners, and Early Stand-Up

Born to Italian parents in Chicago; the family dinner table was ground zero for his comedic storytelling.
“I wasn’t the class clown…I have a natural knack of telling stories and giving it a beginning, a middle, and an end.”
Early interest in stand-up through secretly attending comedy clubs as a teen; career path seemed impossibly distant until he took the leap after college.
[19:19 – 22:03]

7. First Stage Experiences and Parental Support

First time on stage: opening for a national headliner at Northern Illinois, in a “primarily Black room” where he was taunted with calls for the “Sandman” (Showtime at the Apollo reference).
Despite a harsh audience, he “felt at home.”
Parents were highly supportive, despite initial concerns about “health insurance” and the unpredictability of show business.
[22:09 – 24:42]

8. The LA Move: The Waiter Years and Comedy Grind

Moved to LA in 1998 with $10,000, worked as a waiter at the Four Seasons for the “nice place” environment and celebrity regulars.
Took a comedy class to learn the workings of stand-up, then hit open mics “as much as possible.”
Anecdotes of wild gigs: a loose cat running up casino drapes, a heckler wanted to fight him mid-show.
“All that is good battle-tested stuff. So when you go up at Madison Square Garden, you are primed and ready for anything.”
[25:21 – 27:34]

9. Slow-Burn Success, the Vince Vaughn Break, and Grassroots Growth

Between 1998–2005, Sebastian steadily developed his act; the Wild West Comedy Tour with Vince Vaughn in 2005 became a pivotal exposure—a validation and stepping stone from clubs to headlining weekends.
For years, his income depended on low club guarantees and grassroots hustling: “stand outside, shake hands, sell DVDs.”
“Did that for 10, 12 years…then eventually, it grew to a point where we graduated.”
[28:45 – 30:33]

10. First Special and Climbing the Ladder

His first special was funded by a relationship he built while waiting tables at the Four Seasons, for a channel called “Bud TV.”
The journey wasn’t marked by a big break but a “slow burn” built on “just stand up, stand up, stand up.”
[30:57 – 32:17]

11. Relatable Comedy, Nostalgia, and Physicality

His “company bit” (“when the doorbell rings we all hit the floor”) went viral and is emblematic of his style: relatable, multi-generational, and inspired by everyday experience.
On physical comedy: developed over time by experimenting on stage and influenced by comedians like John Ritter:

“Sometimes that’s all it really takes—is an expression or a look on stage, and people will start laughing.”
[33:28 – 37:10]

12. The Arena Era and Pandemic Perspective

Huge milestones: Sold out multiple nights at Madison Square Garden, Boston, Chicago.
Admits he didn’t fully “smell the roses” until the pandemic forced a pause:

“I wish I would have done it, because when I’m in it, I’m not thinking that…before the pandemic…then it was all taken away… I should have enjoyed it...Now I’m enjoying it a little bit more.”
[38:40 – 41:27]

13. Passing on the Drive to the Next Generation

Wants to instill hunger and drive in his own children despite their easier circumstances.
“My challenge now, more so than any standup, is instilling that drive in my kids.”
Shares moments of his children slowly realizing his public profile.
[41:27 – 42:42]

14. Working With Robert De Niro and Transition Into Film

Finds film acting “scarier” and less comfortable than stand-up, because comedians feed off live validation—on a film set, “nobody’s laughing.”
First major film appearances with Joe Pesci and De Niro in The Irishman; surreal to have De Niro later play his father in an autobiographical movie.
On De Niro’s Dedication:

“He wanted to get to know my father. When I called my dad I said, De Niro wants you to come to Oklahoma…My dad’s like, well, how much they paying?...He spent three days with De Niro in Oklahoma…now my dad’s calling me going, this guy’s working me to death!”
The result was poignant:

“I showed the movie to my father. He cried…his life is being depicted in a movie.”
[43:31 – 49:19]

Notable Quotes & Memorable Moments

On art and repetition:

"The trick is, you have to say it like it’s the first time you’re telling the story… you really gotta hone in on the act."
— Sebastian Maniscalco [05:55]
On the DNA of his comedy:

"I’ve always been a person who kind of puts a mirror to what… time frame we’re in… Is it me, or is that guy… da da da?"
— Sebastian Maniscalco [12:29]
On enduring frustration:

"At one point I called home and I said, I don’t know why I’m not getting further along here… It was just a… lot of frustration."
— Sebastian Maniscalco [27:50]
On viral success:

"I didn’t even post that video. Somebody else posted it…that is a multi-generational bit…It’s been my bread and butter."
— Sebastian Maniscalco [33:58]
On De Niro as his dad:

"I would have never thought when I moved to LA March 3, 1998, that we would have a movie coming out with Robert De Niro… It’s crazy."
— Sebastian Maniscalco [49:29]

Timestamps for Important Segments

Gotham Comedy Club memories & filming The Irishman: 03:03 – 04:10
Comedy clubs as the “gym”: 04:23 – 05:01
“Is It Me?”—Special, material & Vegas vibe: 07:40 – 09:18
Family as comedic source: 09:45 – 11:45
Culture, relatability & PC: “Is it me, or…?” 12:25 – 16:04
Origins, Chicago upbringing: 19:19 – 22:03
First time on stage; parents’ support: 22:09 – 24:42
LA grind, working at Four Seasons: 25:21 – 27:34
Wild West Comedy Tour w/ Vince Vaughn: 28:45 – 30:33
How the first special happened: 30:57 – 32:17
The “Company” bit goes viral: 33:28 – 33:58
Physical comedy style: 35:10 – 37:10
Sold out arenas & post-pandemic perspective: 38:40 – 41:27
Parenthood and legacy: 41:27 – 42:42
Acting with De Niro, autobiographical film: 43:31 – 49:19

Final Thoughts

With warmth, humility, and captivating humor, Sebastian Maniscalco illustrates why his rise—though gradual—has resonated so widely. His commitment to relatable, observational comedy, deep family roots, and work ethic appeal to listeners whether they’re comedy aficionados or simply seeking some laughter about the familiar absurdities of modern life. This episode is a must-listen for anyone curious about the grit behind the glamour of stand-up—and the remarkable moments that come when hard work meets opportunity (even if it means having your dad give De Niro a crash course in hair coloring).

Quote to end on:

“It’s been a slow burn for me. For me, it was just stand up, stand up, stand up. No TV, no film, just basically all on the shoulders of comedy.”
— Sebastian Maniscalco [32:17]

Sunday Sitdown with Willie Geist: Sebastian Maniscalco on His Slow-Burn Rise and Working With Robert De Niro

Date: November 22, 2025
Guest: Sebastian Maniscalco

Episode Overview

Key Discussion Points and Insights

1. Returning to Gotham Comedy Club

Nostalgic Memories:
- Sebastian recalls doing “14 shows in one week” at Gotham, which solidified it as his “home away from home in New York.”
- Fun tidbit: The comedy club was transformed into the Copacabana for the filming of The Irishman—the very scene where Maniscalco (as 'Crazy Joe Gallo') has his notable moment with Joe Pesci and Robert De Niro.
- [03:17 – 04:10]

2. The Comedy Club vs. Arena Experience

The Club as Comedy’s Gym:
- Sebastian says, “This is where comedy should be enjoyed… you’re feet away from the performer… it’s tight, everybody’s tightly packed in. For me, I love coming to a comedy club to work out some material. You kind of see what’s good, what’s not.”
- Contrasts the intimacy and experimental freedom of clubs with the heightened expectation of theaters and arenas.
- [04:24 – 05:01]

3. Creating “Is It Me?” and the Vegas/Rat Pack Vibe

Initially planned before the pandemic, the special's material was refined in LA’s Comedy Store and on the road.
On the Vegas Theme: Sebastian says,

“I wanted to do a throwback to the Rat Pack…dressed up in a tuxedo…made the set look a little 1950s, 1960s Las Vegas. I asked the audience to dress up in formal wear, which about 25 of them did.”
- Shares how his parents’ stories of old Vegas imbued the special with nostalgia, and his own desire to “fit in more back maybe with the Rat Pack than I do with people nowadays.”
- [07:51 – 09:18]

4. Mining Family for Material

Sebastian’s mother complains about not making it into the act, joking, “Where am I? People think I’m dead, you know, so my mom wants in, and my dad wants more of him.”
His father—an Italian immigrant and endless source of stories—“parlayed” his son’s success into favors and preferential treatment in Chicago (“I’ve been paying for my dad’s remodel through tickets”).
Classic “immigrant mentality” stories, e.g., his father distrusting painters’ choice of paint:

“He thinks they’re gonna put cheap paint in those buckets. What kind of mindset is this?”
[09:45 – 11:45]

5. Comedy, Cultural Critique, and PC Culture

Maniscalco doesn’t wade into politics but addresses “the environment, the culture,” poking fun at hypersensitivity and nostalgia for when comedy “was supposed to be all in good fun.”
He observes,

“As soon as you start editing your comedy and not doing what you think is funny, you might as well not be doing it because it’s not going to be enjoyable.”
- Adds, “There’s a small portion of society that gets bent out of shape, and those people tend to be the loudest voices.”
- He strives to put his audience at ease, often warning when a bit might “bend them out of shape,” which helps everyone relax.
- [12:29 – 16:04]

6. Origins: Chicago, Family Dinners, and Early Stand-Up

Born to Italian parents in Chicago; the family dinner table was ground zero for his comedic storytelling.
“I wasn’t the class clown…I have a natural knack of telling stories and giving it a beginning, a middle, and an end.”
Early interest in stand-up through secretly attending comedy clubs as a teen; career path seemed impossibly distant until he took the leap after college.
[19:19 – 22:03]

7. First Stage Experiences and Parental Support

First time on stage: opening for a national headliner at Northern Illinois, in a “primarily Black room” where he was taunted with calls for the “Sandman” (Showtime at the Apollo reference).
Despite a harsh audience, he “felt at home.”
Parents were highly supportive, despite initial concerns about “health insurance” and the unpredictability of show business.
[22:09 – 24:42]

8. The LA Move: The Waiter Years and Comedy Grind

Moved to LA in 1998 with $10,000, worked as a waiter at the Four Seasons for the “nice place” environment and celebrity regulars.
Took a comedy class to learn the workings of stand-up, then hit open mics “as much as possible.”
Anecdotes of wild gigs: a loose cat running up casino drapes, a heckler wanted to fight him mid-show.
“All that is good battle-tested stuff. So when you go up at Madison Square Garden, you are primed and ready for anything.”
[25:21 – 27:34]

9. Slow-Burn Success, the Vince Vaughn Break, and Grassroots Growth

Between 1998–2005, Sebastian steadily developed his act; the Wild West Comedy Tour with Vince Vaughn in 2005 became a pivotal exposure—a validation and stepping stone from clubs to headlining weekends.
For years, his income depended on low club guarantees and grassroots hustling: “stand outside, shake hands, sell DVDs.”
“Did that for 10, 12 years…then eventually, it grew to a point where we graduated.”
[28:45 – 30:33]

10. First Special and Climbing the Ladder

His first special was funded by a relationship he built while waiting tables at the Four Seasons, for a channel called “Bud TV.”
The journey wasn’t marked by a big break but a “slow burn” built on “just stand up, stand up, stand up.”
[30:57 – 32:17]

11. Relatable Comedy, Nostalgia, and Physicality

His “company bit” (“when the doorbell rings we all hit the floor”) went viral and is emblematic of his style: relatable, multi-generational, and inspired by everyday experience.
On physical comedy: developed over time by experimenting on stage and influenced by comedians like John Ritter:

“Sometimes that’s all it really takes—is an expression or a look on stage, and people will start laughing.”
[33:28 – 37:10]

12. The Arena Era and Pandemic Perspective

Huge milestones: Sold out multiple nights at Madison Square Garden, Boston, Chicago.
Admits he didn’t fully “smell the roses” until the pandemic forced a pause:

“I wish I would have done it, because when I’m in it, I’m not thinking that…before the pandemic…then it was all taken away… I should have enjoyed it...Now I’m enjoying it a little bit more.”
[38:40 – 41:27]

13. Passing on the Drive to the Next Generation

Wants to instill hunger and drive in his own children despite their easier circumstances.
“My challenge now, more so than any standup, is instilling that drive in my kids.”
Shares moments of his children slowly realizing his public profile.
[41:27 – 42:42]

14. Working With Robert De Niro and Transition Into Film

Finds film acting “scarier” and less comfortable than stand-up, because comedians feed off live validation—on a film set, “nobody’s laughing.”
First major film appearances with Joe Pesci and De Niro in The Irishman; surreal to have De Niro later play his father in an autobiographical movie.
On De Niro’s Dedication:

“He wanted to get to know my father. When I called my dad I said, De Niro wants you to come to Oklahoma…My dad’s like, well, how much they paying?...He spent three days with De Niro in Oklahoma…now my dad’s calling me going, this guy’s working me to death!”
The result was poignant:

“I showed the movie to my father. He cried…his life is being depicted in a movie.”
[43:31 – 49:19]

Notable Quotes & Memorable Moments

On art and repetition:

"The trick is, you have to say it like it’s the first time you’re telling the story… you really gotta hone in on the act."
— Sebastian Maniscalco [05:55]
On the DNA of his comedy:

"I’ve always been a person who kind of puts a mirror to what… time frame we’re in… Is it me, or is that guy… da da da?"
— Sebastian Maniscalco [12:29]
On enduring frustration:

"At one point I called home and I said, I don’t know why I’m not getting further along here… It was just a… lot of frustration."
— Sebastian Maniscalco [27:50]
On viral success:

"I didn’t even post that video. Somebody else posted it…that is a multi-generational bit…It’s been my bread and butter."
— Sebastian Maniscalco [33:58]
On De Niro as his dad:

"I would have never thought when I moved to LA March 3, 1998, that we would have a movie coming out with Robert De Niro… It’s crazy."
— Sebastian Maniscalco [49:29]

Timestamps for Important Segments

Gotham Comedy Club memories & filming The Irishman: 03:03 – 04:10
Comedy clubs as the “gym”: 04:23 – 05:01
“Is It Me?”—Special, material & Vegas vibe: 07:40 – 09:18
Family as comedic source: 09:45 – 11:45
Culture, relatability & PC: “Is it me, or…?” 12:25 – 16:04
Origins, Chicago upbringing: 19:19 – 22:03
First time on stage; parents’ support: 22:09 – 24:42
LA grind, working at Four Seasons: 25:21 – 27:34
Wild West Comedy Tour w/ Vince Vaughn: 28:45 – 30:33
How the first special happened: 30:57 – 32:17
The “Company” bit goes viral: 33:28 – 33:58
Physical comedy style: 35:10 – 37:10
Sold out arenas & post-pandemic perspective: 38:40 – 41:27
Parenthood and legacy: 41:27 – 42:42
Acting with De Niro, autobiographical film: 43:31 – 49:19

Final Thoughts

Quote to end on:

“It’s been a slow burn for me. For me, it was just stand up, stand up, stand up. No TV, no film, just basically all on the shoulders of comedy.”
— Sebastian Maniscalco [32:17]

STAND-UP GREATS: Sebastian Maniscalco on His Slow-Burn Rise and Working With Robert De Niro

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Summary

Sunday Sitdown with Willie Geist: Sebastian Maniscalco on His Slow-Burn Rise and Working With Robert De Niro

Episode Overview

Key Discussion Points and Insights

1. Returning to Gotham Comedy Club

2. The Comedy Club vs. Arena Experience

3. Creating “Is It Me?” and the Vegas/Rat Pack Vibe

4. Mining Family for Material

5. Comedy, Cultural Critique, and PC Culture

6. Origins: Chicago, Family Dinners, and Early Stand-Up

7. First Stage Experiences and Parental Support

8. The LA Move: The Waiter Years and Comedy Grind

9. Slow-Burn Success, the Vince Vaughn Break, and Grassroots Growth

10. First Special and Climbing the Ladder

11. Relatable Comedy, Nostalgia, and Physicality

12. The Arena Era and Pandemic Perspective

13. Passing on the Drive to the Next Generation

14. Working With Robert De Niro and Transition Into Film

Notable Quotes & Memorable Moments

Timestamps for Important Segments

Final Thoughts

Summary

Sunday Sitdown with Willie Geist: Sebastian Maniscalco on His Slow-Burn Rise and Working With Robert De Niro

Episode Overview

Key Discussion Points and Insights

1. Returning to Gotham Comedy Club

2. The Comedy Club vs. Arena Experience

3. Creating “Is It Me?” and the Vegas/Rat Pack Vibe

4. Mining Family for Material

5. Comedy, Cultural Critique, and PC Culture

6. Origins: Chicago, Family Dinners, and Early Stand-Up

7. First Stage Experiences and Parental Support

8. The LA Move: The Waiter Years and Comedy Grind

9. Slow-Burn Success, the Vince Vaughn Break, and Grassroots Growth

10. First Special and Climbing the Ladder

11. Relatable Comedy, Nostalgia, and Physicality

12. The Arena Era and Pandemic Perspective

13. Passing on the Drive to the Next Generation

14. Working With Robert De Niro and Transition Into Film

Notable Quotes & Memorable Moments

Timestamps for Important Segments

Final Thoughts