Greg Fitzsimmons

Tarrytown, a radio father and a bombed set in Boston

Gregory Sebastian Fitzsimmons was born in New York City on 5 April 1966 and grew up in Tarrytown, up the Hudson from the city. The broadcasting came first from his father: Bob Fitzsimmons, who died in 1993, was a New York radio and television presenter and hosted the Jerry Lewis muscular dystrophy telethon every Labor Day from 1973 to 1989. Growing up with a father whose job was talking into a microphone set the terms of what his son would later do for a living, in clubs rather than on a telethon stage.

He went to Boston University, performing with the campus troupe Uncontrolled Substance while finishing his degree, and turned professional as a stand-up in 1988. The drinking that ran through his Irish Catholic family ran through him too — he has described starting at thirteen, behind the bleachers — and it ended after he bombed a set in Boston. Speaking on the recovery podcast Drunk-ish in an episode released on 8 April 2025, he explained why he has never used the word sober about himself, why Alcoholics Anonymous was not a fit, and why he treats comedy itself as the thing that got him out. That distinction matters to the act: the material about not drinking is reported rather than preached.

The first national breaks came in the mid-1990s. He made his debut on the Late Show with David Letterman in 1996, hosted the MTV quiz Idiot Savants across 1996 and 1997, and taped a half-hour Comedy Central Presents in 1998, returning for a second half-hour on the same strand in 2006.

Two decades inside other people's shows

For much of the 2000s the stand-up subsidised, or was subsidised by, a writing career. Fitzsimmons wrote for Politically Incorrect with Bill Maher, The Man Show, Cedric the Entertainer Presents, The Wanda Sykes Show and HBO's Lucky Louie. The most decorated stretch was The Ellen DeGeneres Show between 2003 and 2005, where his work as writer and producer brought four Daytime Emmy Awards. He has not been sentimental about that room: in a 2010 interview on The Howard Stern Show he called the working environment there toxic, years before the subject became a news story of its own. Earlier awards include a jury prize at the HBO Comedy Arts Festival and a CableACE.

On camera he was a fixture of the panel-and-clip format, commentating on VH1's Best Week Ever from 2004 to 2009 and turning up on Chelsea Lately across 41 episodes between 2010 and 2014. He wrote on and appeared in all three seasons of HBO's Crashing, Pete Holmes's series about the bottom rungs of the New York club circuit, and had a role in Netflix's Santa Clarita Diet. In 2010 Simon & Schuster published Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox, built around the letters his mother received from his schools.

Eleven years between hours

The recorded stand-up is thin on the ground by modern standards, which is partly the point. After the two Comedy Central half-hours came Life on Stage, a full hour that premiered on Comedy Central in 2013 and later moved to Netflix and Prime Video; LA Weekly placed it among its top ten comedy releases of that year.

The follow-up took eleven years. You Know Me was filmed at Joe Rogan's Comedy Mothership in Austin in November 2023 and premiered on Fitzsimmons's own YouTube channel on 27 August 2024, running 53 minutes. He directed it and executive produced with Matt Schuler; 800 Pound Gorilla produced, with Jarad Clement and Valentijn Sloot. The hour covers 34 years without drinking, sex with a woman in her fifties, the problem of persuading his children he is cool, and the loneliness of the road — and lands, in the announcement's phrasing, on the position that he is happy where he is.

Putting it out free on YouTube rather than shopping it to a streamer was a deliberate route, and the response came in the same register. Audience notes on Letterboxd place him near Bill Burr and Norm Macdonald, with one reviewer offering the backhanded formulation of a Burr without the money and therefore crankier still. Another picked up the hour's own self-assessment: a comic somewhere in the middle of the pack who has made peace with it.

A microphone most days

Fitzsimmons has kept an unbroken broadcast habit alongside the touring. He hosted The Greg Fitzsimmons Show on SiriusXM's Howard 101 from 2006 to 2018 and has made more than fifty appearances on The Howard Stern Show proper, plus a long run of visits to The Joe Rogan Experience.

The podcast work is now the main daily output. Fitzdog Radio passed 1,000 episodes in August 2023 and reached number 1,130 on 17 March 2026, with Neal Brennan turning the interview around on his host. The early months of 2026 brought Dave Attell on 9 January, Jeff Garlin on 14 January, Jay Mohr on 21 January, Ian Bagg on 28 January, Matt McCusker from Austin on 4 February, Jim Norton on 11 February and Ali Siddiq on 2 March. Sunday Papers, a weekly news-of-the-weird show with Mike Gibbons, hit its 300th episode on 9 February 2026 and was past 310 by late April, still running through August with items on Sturgis, a self-driving toilet and Carlos Mencia's tax arrest. A third show, Childish, is made with Alison Rosen.

Standing in autumn 2026

Nothing about the present setup suggests a comic winding down. The St Patrick's Day show he hosts every year at the Hollywood Improv's main room ran again on 17 March 2026, billed with Sarah Silverman, Caroline Rhea, Laura Kightlinger, Doug Benson and Amber Easton. January 2026 included a late slot at the Comedy Mothership in Austin on the 31st.

The diary for the rest of the year is club-shaped rather than theatre-shaped. He plays the Hollywood Improv on a mixed bill alongside Anthony Jeselnik, Donnell Rawlings, Amir K, Kira Soltanovich, Paul Elia and Saul Trujillo, then heads out: the Dalton Convention Center in Dalton, Georgia on 23 October, Brushy St Commons in Austin on 24 October, Room 47 in Waterloo, Ontario on 25 October and the Rivoli in Toronto on 27 October — all of them double shows. Three nights at the Punch Line in San Francisco follow from 3 to 5 December, with two shows on the Friday and Saturday. His own listings carry more beyond that: Skankfest in New Orleans in mid-November, a Key West run, New Year's Eve at Helium in Portland and a return to the Comedy Mothership in January 2027.

Earlier in this cycle he worked the same rooms — three nights at Comedy Works Downtown in Denver in September 2025, the Comedy Store in La Jolla, and a December 2025 weekend at the SF Punch Line where tickets started at $32.05 and one attendee came away calling it spectacular.