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This documentary begins with footage of controversial comedian Lenny Bruce filing a lawsuit charging that some of the jurors hearing one of his obscenity trials perjured themselves in their voir dire questionnaires by claiming that they had not previously heard of him. As Bruce presents evidence that six of the jurors now admit that they knew of him and therefore could have been biased, voice-over narration states that toward the end of his life, the embittered Bruce had "stopped laughing" due to his escalating financial, legal and personal woes. Over footage of police brutality, and sex and violence in newsreels and theatrically released motion pictures, Bruce is heard "riffing" about the reasons for negative reactions to authority, and that, if it is true that children are influenced by the sex and violence they see in the media, he would rather his child see a "stag movie" than the 1961 film King of Kings . Bruce then laughingly asserts that there should be a statute of limitations on "goyish" accusations about Jews killing Christ, although he is willing to proffer that it was his own family, specifically his uncle Morty, who committed the crime if it will end the religious and racial wrangling. Over news footage of the Vietnam War, Bruce continues his societal barbs, claiming that "they don't like Americans anywhere" because U.S. soldiers used chocolate bars to obtain sexual favors from women in foreign countries. The narrator then discusses the difficulties of Bruce's childhood, during which he drifted from home to home after the divorce of his parents. At the age of sixteen, Bruce joined the U.S. Navy and saw action in World War II in Europe. Upon returning to the United States, Bruce sought his show business break and, "like a number of other cool hipsters, found an angle, being offensive." One of the first influential people to champion Bruce was television host Steve Allen, who welcomed Bruce on his show several times. In a clip from The Steve Allen Show , the host introduces Bruce as "the most shocking comedian of our time." Although he teases the on-air censors, Bruce promises to "behave himself" by sticking to his rehearsal script. Foregoing his usual swear words, both in English and Yiddish, Bruce delivers a routine on various subjects, including words that offend him, such as segregation, and television shows that exploit homosexuality, narcotics and prostitution under the guise of offering help. Acting out all the characters, he describes the adventures of a young boy who sniffs airplane glue, and lampoons Hollywood movies that offer cloying "brotherhood" messages. In 1959, according to the narrator, Lenny polished his free-form, jazz-like method of delivery, and had to be careful not to offend with his more shocking routines when he appeared on television. As the narrator observes, Bruce never hit it big in television, instead becoming famous in nightclubs attended by "barmaids, jazz musicians and bunnies, the freaks of the `50s " In an interview, fellow comic Mort Sahl asserts that Bruce, despite his skewering of middle-class mores, was actually very middle-class and sentimental himself. Bruce again tries to break into television, and in footage from a pilot, describes his latest record, The Sick Humor of Lenny Bruce . Although Bruce admits that there are some "pretty far out bits" on the album, he states that there are no scatological references and then performs "one sick bit," about a real-life bomber who blew up an airplane carrying his mother. According to the narrator, Bruce's self-deprecating humor was better appreciated in person, and his fame grew on college campuses and hip nightspots around the country. After marrying former stripper Honey Harlowe, Bruce and Honey have a daughter named Kitty, whom Bruce adores. The unhappy marriage fails, however, and as Bruce's drug usage, mainly of speed and heroin, increases, his routines become both more introspective and more caustic of hypocrisy. The narrator asserts that Bruce's routines "rang with truth and beauty," and clips from some of his famous sketches about sex and the battle between the sexes are heard. In an interview, influential critic Kenneth Tynan applauds Bruce's unique ability to shed light on society's deepest inhibitions and laments his prosecutions for obscenity, pointing out: "How can any sane, civilized human being be afraid of four letters?" Bruce was arrested for the first time in Philadelphia, on a narcotics charge, and over the following two years, was arrested six more times as well as being banned from performing in London and Australia. Despite his legal troubles, Bruce still believed in the courts and began discussing his experiences on stage. In an interview, British social commentator Malcolm Muggeridge asserts that to arrest Bruce for obscenity was "completely absurd," especially in Chicago, "a city famous for vice and corruption." The narrator notes that after Bruce's many arrests, café and nightclub owners were leery of booking him, as they feared legal harassment. In another commentary on his arrests, Bruce states that he is persecuted because he keeps "picking on the wrong God," and that if he lampooned the gods worshipped by other cultures instead of the "Western God," he would not be a target. Bruce's most controversial, and last, arrest for obscenity occurred in April 1964, at Manhattan's trendy Café Au Go Go. Arrested along with Bruce were the club's owners, Howard and Ella Solomon. Describing Bruce as "on the run," the narrator notes that the increasing pressure caused Bruce to quarrel with numerous lawyers and to act as his own counsel on several occasions. Although Bruce was charged with only a misdemeanor in New York, he was sentenced to four months in the workhouse after being found guilty, which one of his lawyers, Martin Garbus, claims was due to overzealousness on the part of the prosecutors. Former Assistant District Attorney Vincent Cuccia admits that there was pressure from "the establishment" to punish Bruce for his stinging satire, and asserts that now, he would refuse to be involved in such an unjust case. Writer Nat Hentoff then relates that toward the end of his life, Bruce, bankrupt and unable to obtain work, was deeply depressed and obsessed with asserting his right to free speech. Hentoff interviews Bruce for a Canadian television show, and the haggard Bruce states that even though it is "chic" to arrest him, he still "digs" being in front of an audience. Footage of Bruce's nude corpse is then shown after his narcotics overdose in his Hollywood home, with dozens of reporters milling around until the body is finally removed. In a memorial service for the comic, Reverend William Glenesk asserts that Bruce was "a man uptight against an artificial world, who shattered its facades and hypocrisies." The film ends with television footage of Bruce performing a skit about a lonely man who misses his ex-wife and sings that he will always be "all alone."