Sunday Sitdown with Willie Geist: Jim Gaffigan on the Craft of Comedy and His Bourbon Born Out of Chaos

Date: November 23, 2025
Host: Willie Geist
Guest: Jim Gaffigan
Location: City Winery, New York City (Live Audience)

Episode Overview

In this live edition of “Sunday Sitdown,” Willie Geist sits down with acclaimed stand-up comedian Jim Gaffigan for a wide-ranging, engaging conversation. They discuss Jim’s celebrated comedy career, his creative process, the origins and meaning of his new Father Time Bourbon, and how his personal life—particularly his large family—informs his work. The episode is rich with candid anecdotes, audience interaction, and Jim’s characteristic wit, offering both laughter and thoughtful reflection on career, parenting, and the ever-changing landscape of standup comedy.

Key Discussion Points & Insights

Launching Father Time Bourbon

• [03:49 – 07:35] Jim and Willie toast with Father Time Bourbon and Jim shares with the audience, joking:

  • “Every audience member here is going to receive a new car. Wow ... Well, instead of a car, we’re going to give you a sample of Father Time bourbon.”
    – Jim Gaffigan, 03:58–04:13
  • The inspiration: a nightly pandemic ritual of bourbon with his wife while quarantined with their five children. The product’s slogan, “A father’s joy is earned,” refers to bourbon as a reward for making it through parenthood.
    • “This is the father time that someone enjoys when they’re away from their kids.”
      – Jim Gaffigan, 05:35

• Process of creating a celebrity bourbon:

  • Guided by college buddy Stu Pollard, Jim taste-tested over 100 different bourbons before finalizing the blend.
  • “There are a lot of celebrity spirits, and some of them are garbage … I truly love the American whiskey world. My bourbon obsession is less about having a drinking problem. I find it fascinating.”
    – Jim Gaffigan, 06:24–07:35

• On not doing it for money:

  • Jim is involved as a passion project with no major investors:
    • "It's really just me and a college buddy focusing way too much time and energy on this project to the annoyance of our wives."
      – Jim Gaffigan, 08:07–08:33

The Bourbon Comedy Special

• [08:33 – 10:21]

  • Jim’s new YouTube special “Live at Old Forester: The Bourbon Set” features 43 minutes of exclusively bourbon-themed material. He jokes about the niche focus:

    • “If you like whiskey, I think you’ll get a kick out of it. If you’re looking for tequila or brandy jokes, there aren’t any.”
      – Jim Gaffigan, 09:03–09:54

  • Willie lauds Jim’s ability to riff on bourbon for a full hour, “Only he can pull that off.”

Life on the Road & Jerry Seinfeld Story

• [10:21 – 13:12]

  • Jim shares a (hilarious and ultimately fabricated) story of ordering a $500 pour of King of Kentucky bourbon while traveling with Jerry Seinfeld—who, as it turns out, “doesn’t really drink”:

    • “And I had an epiphany in that moment … Jerry will become a bourbon drinker because of me. And Jerry and I can go out drinking expensive bourbon, and Jerry can pay for it. … And then the check came, and I noticed Jerry was looking at it kind of strange ... ‘Your King of Kentuckys cost $500 a pop.’”
      – Jim Gaffigan, 12:14–12:51

  • The punchline: “The only thing I made up is I’ve never met Jerry Seinfeld.”
    – Jim Gaffigan, 13:11

Big Families, Comedy Origins, and Small Town Roots

• [13:49 – 18:07]

  • Jim is youngest of six; much of his material is inspired by both his upbringing and his own five children.

  • Reflects on his grandfather who “stopped the cycle of Gaffigans working in coal mines”—enabling generational upward mobility:

    • “Because of my grandfather … my father was able to go to college … allowed me to be a comedian that tells diarrhea jokes. It’s a real American story.”
      – Jim Gaffigan, 15:59–16:50

  • He double-majored in finance at Georgetown, but always felt a creative pull: “I was definitely raised to seek security ... but, you know, the great irony is all my siblings went into finance; I make a lot more than them.”
    – Jim Gaffigan, 17:06–17:40

Starting Out: Day Jobs, Sleep, and Taking the Risk

• [19:40 – 23:12]

  • Worked in advertising, doing standup by night. Confirmed true: "I had to be woken up at my desk to be fired."

  • “I was just gonna be the weird uncle because it did not look like I was gonna be able to make a living … but at least I enjoy doing standup.”
    – Jim Gaffigan, 20:12–21:19

  • Facing risk and uncertainty, his creative fulfillment outweighed material comfort:

    • “There came a point … I was comfortable with the fact that I’m not going to be on TV or successful. And that was a breakthrough moment for me.”
      – Jim Gaffigan, 23:37

Letterman Breakthrough, Career Milestones, and Parenting Philosophy

• [24:45 – 26:59]

  • Emotional high of performing on Letterman, his childhood idol, in 1999.

    • “When I first heard [Letterman] laugh at one of my jokes, that was amazing. … It’s always two steps forward, one step back—you have to keep a healthy perspective.”
      – Jim Gaffigan, 24:58–25:42

  • Comedy Central hour-long specials transformed his career, enabling him to support his large family solely through comedy.

  • Jokes about inheritance:

    • “My final task of parenting is to leave them with nothing. You know, maybe it’s a romantic notion, but I want them to pay for my casket.”
      – Jim Gaffigan, 26:45–26:59

Using Family as Material

• [27:10 – 28:45]
  • “The benefit of having five children is I can talk about a story … and you can’t be sure which one I’m talking about.”
  • Kids are largely uninterested in his work: “My son came up with the title Dad is Fat. He still hasn’t read it.”
  • Honest about parental regrets in the social media age: “Not only do I wish I never gave my children a phone, I wish … I should never have posted a photo of them.”

Finding His Voice; Approach to Comedy

• [29:28 – 31:25]
  • Inner voice/monologue style evolved as he learned what was “palatable to the audience.”
    • “You really end up with your most authentic self, if that makes sense.”
  • On parenting and creative material: “If your identity isn’t somehow tied up as a father or mother … I think you’re doing something wrong.”

Navigating Comedy as a Career; Editing and Longevity

• [31:33 – 33:40]
  • Success in comedy isn’t just about being funny: “Some of it is editing—the, you know, how much bourbon you consume, your self-assignments … doing things for the right reason.”
  • Even passion projects like the Bourbon set nourish creativity, regardless of commercial potential.

The Boom in Standup: Why Now is the Time

• [33:40 – 36:50]
  • Standup’s popularity is at an all-time high, with many comedians selling out arenas.
  • Streaming, social media, and platforms like YouTube give comedians new ways to reach fans.
    • “There’s something about the awareness of stand up … comedy is booming so much. But I think in this age of AI, in the end, live performance is the safest thing.”
  • Stand-up shows deliver “quality time,” a better entertainment value compared to uncertain movies.

Audience Q&A Highlights

Alternatives to Comedy

• [41:33 – 42:58]
  • Jokes: “Probably a model.”
  • Also interested in farming and advertising, but “getting up early” would be difficult.

Funniest Purdue Football Memory

• [43:29 – 44:49]
  • Walk-on for 10 days: “There was a time when the coach was like, this is the Big Ten, you’re never going to play … it was a very diplomatic way of saying, can you get out of my way?”
  • “I wasn't like Rudy. I was kind of like, I don't know... all right, fine, I’ll just head to Hardee's and eat.”

Parenting Advice

• [45:36 – 47:10]
  • For new parents: “It’s going to get much worse.”
  • For parents of teenagers: “Father Time bourbon.”
  • For college student parents: “It’s going to get much worse … again, yes, it all ties back to Father Time.”
  • Jokes about the hidden conspiracy of “Parents Weekend” existing mainly to boost local hotel profits.

Acting Career & Standup Differences

• [39:01 – 41:04]; [51:00 – 51:28]
  • Loves the creative process in acting, offering nuance to a written character.
  • Auditioning is vulnerable: “Like stripping but you don’t get a dollar.”
  • Favors roles with complexity; cites “Linoleum” and “American Dreamer” as favorites.

How He Listens to Stories as a Comedian

• [52:03 – 52:44]
  • “There is the editing thing that’s always going on, but I think everyone does that, right?”

Notable Quotes & Memorable Moments

• “A father’s joy is earned. … This is the father time that someone enjoys when they’re away from their kids.”
  – Jim Gaffigan, 05:37

• “I find bourbon and American whiskey fascinating. … My bourbon obsession is less about having a drinking problem. It’s more, I find it fascinating.”
  – Jim Gaffigan, 07:18

• “The only thing I made up is I’ve never met Jerry Seinfeld.”
  – Jim Gaffigan, 13:11

• “Because of my grandfather … allowed me to be a comedian that tells diarrhea jokes. It’s a real American story.”
  – Jim Gaffigan, 16:50

• “I was comfortable with the fact that I’m not going to be on TV or successful. That was a breakthrough moment for me.”
  – Jim Gaffigan, 23:37

• “My final task of parenting is to leave them with nothing. … I want them to pay for my casket.”
  – Jim Gaffigan, 26:54

• “If you’re involved [as a parent], that means you’re annoyed. … If you aren’t sometimes, you’re doing something wrong.”
  – Jim Gaffigan, 30:47

• “In this age of AI, in the end, live performance is the safest thing. … the live experience is pretty important.”
  – Jim Gaffigan, 35:34

• “There’s worse things. … For me, it sounds corny, but I love the process so much. So as long as I can, you know, continue to tour and come up with material, that’s the reward.”
  – Jim Gaffigan, 54:23

Memorable Audience Interaction

• [03:49 – Throughout] Jim jokes about giving everyone a “new car” like Oprah, then instead delivers bourbon samples.
• [54:17–55:31] Closes with warmth and gratitude: “As long as I can continue to tour and come up with material, that’s the reward.”

Takeaways

• Jim Gaffigan’s comedy is deeply rooted in his lived and family experience, enhanced by a self-deprecating, authentic delivery honed over decades.
• His foray into bourbon represents his willingness to pursue passions outside comedy, done for fulfillment, not just commercial success.
• The standup landscape is flourishing, with technology and live performance combining to create unprecedented reach and access.
• Even at the peak of his career, Gaffigan remains grounded, focused on the creative process over accolades, and candid about the challenges and joys of both parenting and performing.

Timestamps for Key Segments

• [03:49] – Father Time Bourbon giveaway and origin story
• [06:15] – How to create a celebrity bourbon
• [09:00] – The all-bourbon comedy special
• [10:21] – Jerry Seinfeld/King of Kentucky story
• [15:59] – Generational family story and roots
• [19:40] – Day jobs, napping, and taking the leap into comedy
• [24:45] – Letterman breakthrough and perspective on fame
• [27:10] – Using family as comic fuel
• [33:40] – Standup’s current boom and live performance value
• [39:01] – Acting versus standup: craft and rewards
• [41:33] – Audience Q&A: “If you weren't a comedian…”
• [45:36] – Audience Q&A: Parenting advice
• [54:17] – Looking at the future: process, fulfillment, and legacy

Summary by Sunday Sitdown Podcast Summarizer — capturing the charm, candor, and insight of a live Jim Gaffigan interview for Sunday TODAY fans and newcomers alike.