His 1986 one-man show The World According to Me won a Special Tony Award, an Outer Critics Circle Award, an Ace Award, an Emmy Award, and a Grammy nomination. Later, his 1988 special Jackie Mason on Broadway won another Emmy Award (for outstanding writing) and another Ace Award, and his 1991 voice-over of Rabbi Hyman Krustofski in The Simpsons episode "Like Father, Like Clown" won Mason a third Emmy Award. He wrote and performed six one-man shows on Broadway.[1]

Known for his delivery and voice, as well as his use of innuendo and pun, Mason's often culturally grounded humor was described as irreverent and sometimes politically incorrect.[3][4] A critic for Time wrote that he spoke to audiences: "with the Yiddish locutions of an immigrant who just completed a course in English. By mail." 

Mason made several appearances as a guest on The Ed Sullivan Show during the 1960s.[4] He claimed to have been on the first episode to feature the American television debut of the Beatles, although research does not bear this fact out.[23] Mason revealed during his appearance on the BBC show Desert Island Discs that at the time he did not think much of the group, referring to them as "four kids in search of a voice who needed haircuts". In 1962 he came out with his initial LP record, a best-seller entitled I'm the Greatest Comedian in the World, Only Nobody Knows It Yet, followed by I Want to Leave You with the Words of a Great Comedian.[9][24]

"Middle finger" incident (1964)[edit]

On October 18, 1964, in an appearance on The Ed Sullivan Show, Mason allegedly gave host Ed Sullivan the finger on air. Footage of the incident shows Mason in the middle of doing his stand-up comedy act and then looking toward Sullivan, who had placed himself directly behind the camera, commenting that Sullivan was signaling him.[5][10] Sullivan was reportedly letting Mason know (by holding up two fingers) that he had only two minutes left, and to cut his act short, as the program was about to cut away due to having been partly pre-empted by an impromptu speech by President Lyndon B. Johnson that the show carried.[5][7]

Mason began working his own fingers into his act to make fun of the situation, and pointed toward Sullivan with an index finger, a thumb, but not (as Sullivan mistakenly believed) his middle finger.[5] Sullivan was infuriated by this, and banned Mason from future appearances on the show, canceling Mason's $45,000 ($375,000 in current dollar terms), six-appearance contract.[5][10] Mason denied knowingly giving Sullivan the middle finger; he later said that he had not heard of the middle finger gesture at that time.[7] To clear his name, Mason filed a libel suit on the grounds that Sullivan had defamed him at the New York Supreme Court. That court dismissed most of Mason's complaint. Both Mason and Sullivan appealed to the New York Supreme Court Appellate Division (which reinstated three additional causes of action against Sullivan) in June 1966.[3][25][26][27] He was nevertheless banned from the show for a period of time. Sullivan asserted that Mason was unpredictable and could not be trusted. Because of Sullivan's influence, he was branded as unreliable, volatile, and obscene, and he failed to get substantial TV work for the next two decades.[3][5][7][8] There was no ruling on the merits, merely a determination that Mason's suit could proceed and that he would be given an opportunity to prove his claim.

Mason was given a single comeback appearance on Sullivan's TV program two years later, and Sullivan publicly apologized to him, but the damage was done.[5] At that time, Mason opened his monologue by saying, "It is a great thrill ... and a fantastic opportunity to see me in person again."[26] Mason later appeared on the show five times: April 23, 1967; February 25, 1968; November 24, 1968; July 22, 1969; and August 31, 1969.[28] Mason later said: "It took 20 years to overcome what happened in one minute"