Sunday Sitdown with Willie Geist Jim Gaffigan on the Craft of Comedy and His Bourbon Brand (November 2025)
Feb 1, 2026
Jim Gaffigan, stand-up comedian, bestselling author, and actor known for observational humor, talks career milestones and family life. He breaks down creating Father Time bourbon and the tasting and branding process. He recalls Letterman’s role in his rise and explains how editing shapes his comedic voice. Live-show energy, acting versus stand-up, and why creativity matters round out the conversation.
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Get Expert Help When Building A Spirit
- Acknowledge you need help when launching a spirits project and lean on experts and contacts.
- Do extensive tastings and iterate until you find the right blend, as Jim did with many samples and collaboration.
Choose Platform For Passion, Not Payoff
- Jim deliberately released a niche bourbon-themed special on YouTube knowing mainstream platforms wouldn't favor it.
- He prioritizes creative expression over platform approval when a project serves a passionate audience.
The King Of Kentucky Moment
- Jim recounts ordering an expensive King of Kentucky bourbon for Jerry Seinfeld and learning it cost $500 a pour.
- Jerry disliked it, leaving Jim to absorb the surprise bill and the embarrassing lesson about expensive spirits.
