Greg Fitzsimmons

Greg Fitzsimmons is the kind of comic who’s been quietly killing it for decades—a veteran of stand-up with the sharpness of someone who’s been in the game long enough to call out all its absurdities, yet still hungry enough to keep pushing boundaries. Fitzsimmons blends intelligence, self-deprecation, and brutal honesty into a comedic style that makes you feel like you’re hearing the funniest guy at the bar, except way more polished and way more likely to have an Emmy.

Sharp-Witted and Fearless

Fitzsimmons has a style that’s equal parts thought-provoking and hilariously reckless. He doesn’t just tell jokes—he dissects life, relationships, and society with the kind of biting humor that makes you laugh while rethinking your own perspective. Whether he's talking about fatherhood, show business, or his own flaws, he delivers it all with the confidence of someone who’s seen it all and doesn’t care who he offends.

A Comedy Veteran with Serious Credentials

Born and raised in Tarrytown, New York, Fitzsimmons built his career in the gritty Boston stand-up scene, performing alongside heavy hitters like Bill Burr, David Cross, and Marc Maron. Boston in the ‘90s was a proving ground—comedians had to be fast, sharp, and fearless, or they wouldn’t last. The scene demanded originality, and Fitzsimmons thrived, developing a style that balanced sharp wit with just the right amount of self-destruction.

His talent took him beyond Boston, making him a regular at The Comedy Cellar and landing him spots on The Tonight Show, Conan, and The Late Show with Stephen Colbert. But Fitzsimmons wasn’t just a club comic—he became a four-time Emmy Award-winning writer, contributing to The Ellen DeGeneres Show, Crashing, and Lucky Louie.

Podcasting and Beyond

Beyond stand-up, Fitzsimmons is one of the OGs of comedy podcasting. His show, “Fitzdog Radio”, has been running since 2009, featuring interviews with some of the biggest names in comedy, entertainment, and beyond. His ability to mix hilarious anecdotes with genuine insight makes his podcast a must-listen for comedy fans.

He also co-hosts the wildly popular podcast “Sunday Papers” with fellow comedian Mike Gibbons, where they break down the week’s news with an irreverent, no-BS approach.

A True Stand-Up Lifer

Greg Fitzsimmons is one of those comics who never stops—whether it’s touring relentlessly, writing, podcasting, or making brutally honest observations about life, he’s a constant force in comedy. If you like stand-up that’s smart, fearless, and brutally funny, Fitzsimmons is a name you should already know.