The Dan Le Batard Show with Stugotz

South Beach Sessions – Sebastian Maniscalco

Date: November 13, 2025

Episode Overview

From the Elser Hotel in Downtown Miami, Dan Le Batard and Stugotz sit down with acclaimed comedian Sebastian Maniscalco for an in-depth, wide-ranging conversation. The episode touches on Maniscalco's work ethic, comedic beginnings, life on tour, personal life, family dynamics, therapy, and his evolving sense of success. With his upcoming special "It Ain't Right" on Hulu (November 21st), Maniscalco discusses the pressures and joys of comedy at the highest level and the ongoing push-pull between professional ambition and personal fulfillment.

Key Discussion Points and Insights

1. The Comedy Grind and Living Life for Material

• Comedy as a Lifeline: Sebastian reflects on finishing his latest tour and the need to "recharge, reset and then live life a little bit so I could extract material from life." ([00:57])
• Pressure to Top Yourself: He acknowledges the increasing pressure to keep material fresh and better than before:
  "My material has to be greater to or equal to whatever the hell you saw the last time I was in town. And if that dips, I feel the audience leaves... Not gonna pay a hard ticket price. See a guy who's not at the top of his game." ([01:55])
• Physicality and Longevity: Despite hopes to perform into his 70s and 80s, he notes the challenge:
  "My act is very physical. I'm moving around a lot. I don't know who's gonna come out when I'm 80..." ([03:09])

2. Turning Pain into Comedy

• Comedy as Therapy:
  "When I don't do comedy, I'm not in a good mood, put it that way. This is very therapeutic for me to go up there." ([03:39])
• Mining Life's Discomforts:
  Sebastian processes arguments and even trauma through comedy, but only after time has passed—
  "It's not even happening in the moment because in the moment, it's not funny... You let that marinate for 24 hours..." ([04:52])

3. Biographical Journey & Early Hustle

• Traditional Upbringing: Grew up in Arlington Heights, Chicago, in a loving Italian family with no direct entertainment industry connection.
  "Nothing that would suggest that I was gonna get into the entertainment business..." ([05:48])
• Comedy Club Beginnings:
  He started going to clubs at 16 just to watch, not perform—out of fascination for stand-up ([07:02]).
• LA Comedy Scene:
  "Going night in, night out, working out the material, dealing with hecklers... I stayed. A lot of people get. Say, I'm not gonna stay. I'm like, I gotta stay..." ([08:57])
• Unconventional Gigs:
  Performing in "a boxing ring with a bowling alley behind me... with fresh blood from the night before..." ([10:29])

4. The Waiting Tables Years & Determination

• Work Hustle:
  "I was never a couch surfer... I wanted my own place. I wanted to have a little scratch to walk around and buy stuff..." ([16:46])
• Dish Network Fiasco: Tried selling satellite dishes in a mall—unsuccessfully, leading to debt. ([17:30])
• Paying Debts, Learning Lessons:
  His dad loaned him $10,000, but made him pay every cent back:
  "He was so meticulous about keeping track of what I owed him on a pizza napkin..." ([19:56])
• Hospitality and Regrets:
  Wished he'd appreciated opportunities to learn more as a waiter: "I wish I was a little bit more present with the amount of opportunity around me..." ([15:51])

5. Work Ethic, Social Media, and Modern Comedy Pressures

• Family Influence:
  "No one ever is going to give you anything, and whatever you got to do, you're gonna have to work your ass off for." ([21:10])
• Obsessive Work Habits: Admits to a near-compulsive drive: "You go on this tour for whatever, two years, and my mentality is, what's next?" ([21:10])
• Social Media Ambivalence:
  "If you don't post on social media, it's like you don't even exist... I grew up with like, Prince and Michael Jackson, where, if you saw them, it was like a treat..." ([22:10])

6. Family, Balance, and Aging in Comedy

• Late Marriage and Kids:
  "I didn't want to like have a distraction of a wife or kids... I would feel extremely guilty leaving my young kids and my wife while I went on a six week run." ([29:25])
• Struggles with Balance:
  Now finds ways to prioritize family while still working—"now I know... to spend quality time with my family as well as doing what I love as a comedian" ([31:50])
• Anxiety About the Future:
  "I'll do the math and go, okay, probably about 80. Start falling apart... Am I going to see my daughter get married?" ([32:17])

7. Finances, Success, and Never-Ending Ambition

• Financial Responsibility and Inherited Anxiety:
  "My fear is it's all gonna go away today, so you gotta make more." ([40:21])
• Success = Responsibility:
  "When you come to see my show, I want you to leave going. It's the best comedy I have ever seen in my life. That's the goal for me." ([71:50])
• Stage Perfectionism:
  "As soon as you stumble on a word, the timing's gone... The next word is not going to be as funny..." ([72:30])

8. Relationship with Parents & Emotional Vulnerability

• Father's Influence:
  Sebastian paid back loans in full—his dad now expresses pride:
  "He wrote me a really nice letter and it said he was proud of me..." ([37:13])
• Emotion in the Family:
  With Italian (and Cuban, as Le Batard notes) fathers, expression is hard-won:
  "My dad, I think had a kind of coming of age where he did start..." ([39:09])
• Comedy and Avoiding Grief:
  "I gotta make somebody laugh because I don't want to see my dad cry or my mom cry. I gotta make him laugh. And that's how we snapped out of a lot of, like, grief." ([59:07])

9. Therapy, Introspection, and Vulnerability

• Therapy as Problem Solving:
  "I do therapy, but it's... about current things, you know, it's not about, like, oh, I grew up with trauma." ([60:48])
• Crying and "The Prison of Strength":
  "The cry, as it's coming out, almost wants to go back up. It's like it's totally lost. I don't know what the hell it's doing outside the eyeball." ([64:03])
• Press and Emotions: Public display of emotion during a movie press tour with his father and De Niro. ([64:55])

10. The New Special & Creative Process

• "It Ain't Right" on Hulu (Nov 21st):
  Shot at the United Center in Chicago; first arena special.
  "The way we shot it and... the production value was just phenomenal... I'm really proud of this one. Not so much the last one..." ([65:35])
• Self-Deprecation and Maturity:
  Enjoys leaning into making fun of himself in material:
  "I have the most fun making fun of myself... There’s an 11 minute run that I talk about my health that I love doing." ([67:10])
• Evolution from Anger to Relatability:
  Moved from a guarded, angry stage persona to one "more comfortable on stage, laughing at myself, being self deprecating." ([55:30], [56:27])

11. Professional vs. Personal Fulfillment

• Professional Joy vs. Intimacy:
  Misses intimate club days:
  "I was happier doing comedy clubs and winning over a room of people that didn’t know who I was… there was a joy in that." ([44:42])
• Arena Comedy’s Double-Edge:
  Relishes the success but sees a never-ending chase:
  "Now was that feat… What’s next?... measured success is gonna be." ([45:56])

Notable Quotes & Memorable Moments

• On Work Ethic and Pressure:

  "People spend hard earned money to come out and see you perform. They get a babysitter, they park the car, they make a night of it. And I want them people to leave saying, wow, can't wait till he comes back." — Sebastian Maniscalco ([01:55])

• On Laughing through Grief:

  "We were laughing at funerals, you know what I'm saying? The only way we could cope… was to find a morsel of humor in it." — Sebastian Maniscalco ([03:39])

• On Social Media and Fame:

  "If you don't post on social media, it's like you don’t even exist." — Sebastian Maniscalco ([22:10])

• On Financial Anxiety:

  "My fear is it's all gonna go away today, so you gotta make more. My tongue's gonna fall out." — Sebastian Maniscalco ([40:21])

• On Perfectionism in Comedy:

  "When you stumble on a word, the timing’s gone... the next word is not going to be as funny..." — Sebastian Maniscalco ([72:30])

• On Relationship with His Father:

  "He wrote me a really nice letter and it said he was proud of me." — Sebastian Maniscalco ([37:13])

• On The Burden of Expectation:

  "The expectation of funny is something that you've chosen as a living, and you've met it for 30 years... But you don't always meet yours." — Host ([71:29])

Chapter Timestamps (MM:SS format)

• 00:57 – The grind of comedy tours and the need to recharge for new material
• 03:09 – Physicality in comedy and wishing to perform into old age
• 05:48 – Maniscalco’s biographical roots and early love for comedy
• 10:29 – Performing in odd venues (boxing rings in bowling alleys)
• 14:21 – Working as a waiter at the Four Seasons and learning about customer service (or not)
• 17:30 – Attempting sales (Dish Network); going into debt
• 19:56 – Father gives a loan; Sebastian is made to pay every cent back
• 22:10 – Pressures of being relevant in the social-media era
• 29:25 – Deliberate late start with marriage and kids; workaholic tendencies
• 31:50 – Learning to balance family and career later in life
• 37:13 – Father expresses pride in a letter after Sebastian gifts him a car
• 40:21 – Anxiety about money and success: "My fear is it's all gonna go away..."
• 44:42 – Nostalgia for early comedy club days; the joy of the struggle
• 55:30 – Evolving from angry, guarded comedy to more relatable, self-deprecating style
• 65:35 – New special "It Ain’t Right": arena taping, production values, pride in work
• 71:29 – The burden and terror of the 'expectation of funny' in comedy

Episode Closing

Sebastian articulates the perpetual tension between drive for success and capacity for joy, underscoring that even for top performers, the struggle for balance, relevance, and purpose never truly recedes.

"I'm really proud of this one. Not so much the last one... I think you have to put the bar extremely high to meet people's expectations and to meet my own expectations." — Sebastian Maniscalco ([65:36], [70:41])

Episode Links

• Sebastian Maniscalco Special: It Ain’t Right on Hulu, Nov 21
• Tour Tickets & Dates: SebastianLive.com

This summary captures the heart of a revealing, funny, and poignant conversation about the mechanics of comedy, the cost of striving, and the constant evolution of a performer who has reached the top but keeps pushing for more.