Jim Gaffigan Joins Willie Geist for a Packed Sunday Sitdown Live at City Winery in New York City

Jim Gaffigan sat down with Willie Geist for a special live edition of Sunday Sitdown Live at City Winery in New York City, drawing a full audience as part of the inaugural TODAY Fan Fest. The event took place on November 10, 2025, at the venue’s Pier 57 location, offering fans an up-close look at Gaffigan’s latest ventures and personal reflections. Tickets for the session were made available to the public, giving attendees the chance to watch a live taping of the well-known interview series.

The conversation highlighted Gaffigan’s growing interest in the world of bourbon, especially through his venture Fathertime Bourbon, which he recently introduced as a limited-run Kentucky bourbon brand. Gaffigan explained that themes of fatherhood, aging, and the chaotic charm of raising five children played a major role in inspiring the project.

He has described the brand with his signature humor, once joking in an interview with Cigar & Spirits that “alcohol is not the answer, but it’s pretty close,” when talking about the challenges of parenthood. You can read that interview here.

Gaffigan also touched on growing up in Indiana, sharing how he developed a “secret dream of comedy” long before making it a career. Raised in Chesterton, he later moved into advertising before taking the leap into stand-up—something that shaped much of his grounded, observational humor. His background continues to influence both his comedic style and the personal tone behind his bourbon branding. A general overview of his life and career can be found on his Wikipedia page.

A major point of interest during the event was Gaffigan’s whisky-centered comedy special Live from Old Forester: The Bourbon Set, which was released as a surprise drop on November 23, 2025. The special was filmed at the historic Old Forester distillery and ties directly into his recent bourbon enthusiasm. While independent details remain limited, references to the special note that it blends his stand-up style with the atmosphere of a classic Kentucky barrel house. The mention of this project appears in publicly editable sources, so viewers may learn more as official material becomes available.

The taping itself was designed to give fans a more intimate version of the typical Sunday Sitdown format. City Winery’s relaxed setting created an environment where Gaffigan and Geist could blend comedy, storytelling, and behind-the-scenes discussion without the stiffness of a studio setup. According to the official event listing, the session was promoted as a chance to “be in the room” for a unique live conversation, further elevating the fan experience. Details remain available on the event page here.

Gaffigan’s appearance at the live event also aligned with his Everything Is Wonderful! Tour, which included the New York date at City Winery. His broader tour schedule can be found on his official website JimGaffigan.com. The combination of the tour stop, the bourbon launch, and the live interview created a timely opportunity for fans to hear about multiple new projects directly from Gaffigan himself.

Overall, the Sunday Sitdown Live event showcased a blend of Gaffigan’s comedic roots, his personal life, his entrepreneurial jump into bourbon, and his latest entertainment releases. With a packed house, strong audience response, and a conversational atmosphere, the session served as a standout moment within the TODAY Fan Fest lineup and highlighted why Gaffigan remains one of the most relatable voices in comedy today.