Stand-up
Norton wished to pursue a career as a stand-up comedian when he was 12. He took an interest to comedy after his mother brought home comedy albums from work, and names Richard Pryor, George Carlin, Woody Allen, and Robert Klein as his influences. Norton performed his first stand-up routine in April 1990 at an open mic night at Varsity, a pub in Sayreville, New Jersey, when he was 21. He later described his performance as "awful." Norton credited Pat Gaynor for putting him on stage that night, and Ward and John Magnuson of Rascals comedy club as being "instrumental" in his early development. Following his debut, Norton spent five years working on his stand-up traveling to New York, New Jersey, Boston, Pennsylvania, Maryland, and Florida with comedians Jim Florentine and Bob Levy, who were coming up at the same time. Norton developed an act based on self-deprecating humor, which came naturally to him and gained encouragement when other comedians told him they enjoyed it. Around ten years into stand-up, Norton felt he had found his voice and felt comfortable enough on stage.
Norton had a breakthrough in 1997 after comedian Andrew Dice Clay noticed his appearance on The Louie Show and asked him to be his opening act on his tours when his original pick cancelled at the last minute. The two first met at the Comedy Store in Los Angeles where Norton was doing his first gig at the venue, and learned Clay wished to go on stage after him. Norton went on to open for Clay in the course of the following three years, playing large venues including Madison Square Garden in New York City in 2000.
The absence of Opie and Anthony from the airwaves between August 2002 and October 2004 encouraged Norton to write and develop his stand-up act. Soon after the show's cancellation, he underwent his Yellow Discipline Tour. In 2003, he had assembled a new 45-minute set and assembled his first comedy album, Yellow Discipline, which was followed by Trinkets I Own Made from Gorilla Hands, in April 2005. Soon after, Norton filmed his first half-hour HBO comedy special as part of the network's One Night Stand series, at NYU's Skirball Center for the Performing Arts after his manager informed him of the chance to perform a showcase in the New York City area. In 2004, Norton was voted best comedian and breakthrough performer of the year on Cringe Humor. Following his return to radio in 2004, Norton began a weekday routine of doing radio in the morning and performing short sets in a New York City comedy club, mostly the Comedy Cellar, in the evening to work on new material. From 2006 to 2008, Norton featured on every show of the annual Opie and Anthony's Traveling Virus Comedy Tour. In 2008, Norton hosted a four-part show on HBO titled Down and Dirty with Jim Norton that featured Lemmy as its musical director. He had Amy Schumer be his opening act in her early career.
Norton had a productive start in the 2010s, writing and releasing three hour long specials in three and a half years. He released his first, Please Be Offended on the television channel Epix in June 2012, and features Ozzy Osbourne sitting on a toilet introducing Norton. He chose the network as they allowed him complete creative freedom and were willing to promote his product. Norton followed it with American Degenerate, his second for Epix, which aired in August 2013 before it was released on Netflix that November. In April 2015, Norton released his fourth Epix special, Contextually Inadequate. Within three months of its release, Norton was touring with a new hour of material. In the following year, Norton described his career as "stagnant... there's nothing happening."
In 2017, Norton's special A Mouthful of Shame debuted on Netflix. He promoted it with the 31-date Mouthful of Shame Tour, his first nationwide theatre tour as headliner, throughout 2016. The special includes an opening with Robert De Niro spanking Norton's bare bottom. Later in 2017, Norton embarked on his first stand-up tour of Europe. He signed with WME to pitch ideas for his own series on Netflix. He appeared in Season 2, Episode 1 of the Netflix standup comedy series "The Degenerates," released on December 31, 2019.