Lenny Bruce

Though he became one of the most controversial figures of the 1950s and ‘60s, Lenny Bruce started out on the seedy side, cracking up dingy rooms full of randy drunks between the dancers at strip clubs. Eventually, the freedom afforded by this scenario led him to develop the outrageous, iconoclastic, stream-of-consciousness style that made him famous. By the late ‘50s, he was a cult phenomenon, and a hero of the burgeoning counterculture. A Kerouac of stand-up comedy, his jazz- and beat-poetry-influenced, improvisatory approach skewered sacred cows from religion to politics and openly mocked square social propriety. The latter proved his undoing, as the ‘60s found him mired in a seemingly endless series of obscenity trials. His performances veered further and further from straightforward comedy towards freeform philosophizing and an obsessive examination of his legal wrangles. Persecuted by the law and blacklisted by clubs, he began to lose himself in drugs, and died of an overdose in 1966. Though he never knew it, Bruce paved the way for legions of comics, from George Carlin and Richard Pryor to Bill Hicks and Sam Kinison, and his name became synonymous with the power of free speech.