Indiana native Jim Gaffigan arrived in New York City in 1990 at the age of 24. Officially, he had relocated to work in advertising, but his real fascination with New York had a lot more to do with pursuing his dream of making people laugh as an actor and stand-up comic, a dream he would eventually realize through hard work and ample talent. Gaffigan says he came from "a conservative family where you're driven by security, and wearing a tie to work is considered a success. My uncle was the first one to go to college and, at that point, we'd been in this country for 150 years. It took us five generations to get to the middle class, and I was like, "Hey, I think I'm gonna go into the entertainment world!" Everybody was like, "Are you nuts?"
Gaffigan proved his comic merit and steadily climbed the ladder to stand-up success, eventually landing an appearance on The Late Show with David Letterman which led to a sitcom gig that never fully played out. Gaffigan's early struggles in television had a cathartic effect on Gaffigan's stand-up routine. "His observational humor lost a lot of its initial peevishness, and it now relies on his hyper-awareness of his own mundanity, expressed in an 'inner voice' that comments on his act throughout the show," says The AV Club.