In 1986, he moved back to New York where he tentatively made his first efforts at stand-up comedy. His first gig was at the club – ‘The Bitter End’. It was at this time he switched his name to Stewart as he felt it was easier to pronounce. It also was due to a part estrangement with his father.
Despite a nervous beginning, Stewart developed a good reputation and was given prime-time gigs at the Comedy Cellar, and this helped land him his first writing jobs for TV – ‘Caroline’s Comedy Hours’ and a short part on MTV’s ‘You Wrote it, You Watch it’.
In 1993, Stewart received his first big break, appearing on NBC’s Late Night with David Letterman. Although he was close to getting Letterman’s job, he just missed out. Stewart went back to MTV where he developed his first talk show – ‘The Jon Stewart Show’ – this became one of MTV’s most popular shows.