A product of Boston, Gulman has been a scholarship college football player, an accountant, and a high school teacher. He has made countless television appearances as both a comedian and an actor and is one of only a handful of comedians to perform on every single late-night comedy program.

Gulman has made four successful TV specials including his most recent critically acclaimed stand-up special for HBO, The Great Depresh, a tour de force look at mental illness, which is equal parts hilarious and inspiring. In 2019 he appeared in the international blockbuster Joker. He was most recently seen co-starring with Amy Schumer in the hit Hulu comedy series, Life & Beth.