Greg Fitzsimmons
Gregory Sebastian Fitzsimmons (born April 5, 1966) is an American stand-up comedian , television writer, producer, and podcaster recognized for his incisive wit and scathing sarcasm. With more than 35 years in the comedy industry, Fitzsimmons has earned four Daytime Emmy Awards as a writer and producer on The Ellen DeGeneres Show . Fitzsimmons began his career honing stand-up in Boston before gaining prominence through writing credits on shows such as HBO's Lucky Louie , The Man Show , and the Emmy Awards broadcast, as well as contributing to Crashing on HBO . He has released comedy specials and performed extensively on late-night television , including frequent guest spots on Late Show with David Letterman , Late Night with Conan O'Brien , and Jimmy Kimmel Live! . As a podcaster, he hosts Fitzdog Radio —available on SiriusXM and independently—along with Sunday Papers and Childish , often interviewing comedians and entertainers. His work emphasizes personal anecdotes on sobriety, family, and the challenges of life on the road, reflecting over three decades of sobriety.
Gregory Sebastian Fitzsimmons was born on April 5, 1966, in New York City to Patricia Marie Judith McCarthy and Bob Fitzsimmons , a radio personality whose career exposed the young Greg to the world of broadcasting and entertainment from an early age. The family relocated to Tarrytown, New York , where Fitzsimmons spent his formative childhood years in a household shaped by strong Irish-American traditions, with all four grandparents having immigrated from Ireland to the Bronx .
This Irish Catholic background instilled a distinctive cutting sensibility and sense of resentment-tinged humor, which Fitzsimmons later credited as foundational to his comedic voice, reflecting the sharp-witted, sardonic style common in such family dynamics. His father's profession in radio further influenced his early fascination with performance and media, providing indirect mentorship through exposure to on-air storytelling and audience engagement, though Fitzsimmons has described his youth as marked by mischief and disciplinary challenges detailed in his memoir Dear Mrs. Fitzsimmons .
Prior to pursuing comedy, Fitzsimmons attended Boston University , graduating in 1989 from both the College of General Studies and the College of Arts and Sciences, where he first experimented with humor through the student troupe Uncontrolled Substances, bridging his upbringing's irreverent influences to his emerging professional interests.
Fitzsimmons initiated his stand-up comedy pursuits during his undergraduate years at Boston University , graduating in 1989 from the College of General Studies and College of Arts and Sciences, where he participated in the campus comedy troupe Uncontrolled Substances. He entered the professional circuit in the late 1980s amid Boston's robust comedy environment, undertaking demanding club performances, including alongside emerging comedian Joe Rogan . This period marked his immersion in a scene noted for its intensity and talent development, fostering skills through repeated exposure to varied audiences.
Transitioning rapidly, Fitzsimmons achieved full-time status as a comedian within about 18 months of commencing performances, capitalizing on the era's expanding opportunities for stand-up acts. His early career involved grinding through smaller venues in Boston and subsequently New York, refining a style characterized by sharp observational humor and self-deprecating anecdotes drawn from personal experiences. By the early 1990s, he had established a presence on national television through guest spots on programs like Late Night with Conan O'Brien and Late Show with David Letterman , which amplified his visibility and booking prospects.
