Outside every American comedy club there ought to be a statue of Lenny Bruce—the type of big bronze statue that commemorates and immortalizes heroes. Bruce, who died 50 years ago today—long before the stand-up boom—changed comedy. His style, with its uncensored language, jazzlike rhythm and fearless honesty, was entirely new.

“Lenny Bruce was the linchpin between the old school of comedy and what would become Pryor and Carlin and everything that spawned afterward,” says comedian Lewis Black. “He’s the missing link.” Bruce replaced the previous generation’s tepid mother-in-law jokes with brilliant and brave satire on religion, race, sex, drugs and politics. And he did it in the pages of Playboy as well.

How to Talk Dirty and Influence People, Bruce’s gleefully provocative autobiography, was serialized in six parts by Hugh Hefner, starting with the October 1963 issue of Playboy, before it was published as a book. To mark the 50th anniversary of Bruce’s death, this month Da Capo Press is rereleasing How to Talk Dirty. Bringing Bruce’s ideas and stories to a new generation might just be the next best thing to erecting those bronze statues.

Lenny Bruce was the linchpin between the old school of comedy and what would become Pryor and Carlin and everything that spawned afterward.

Lewis Black

In 1959, Hef had flown to San Francisco to catch Bruce’s act. In short order he helped get the comic into Chicago clubs, profiled him in the Playboy piece “Rebel With a Caustic Cause” and featured him on the TV show Playboy’s Penthouse. But perhaps the highest-profile platform Bruce had was those six issues of Playboy and the subsequent book—rather remarkably, considering that in 1963 both Hef and Bruce were facing obscenity charges, Hef for publishing the Jayne Mansfield pictorial and Bruce for his stage material.

“Not only was Hugh Hefner showing pictures of women, but he was putting an author in the magazine who had an open mindset that other people simply didn’t have back then,” says Kitty Bruce, Lenny’s daughter. To understand that mindset in the context of the early 1960s is to understand Lenny Bruce’s uncommon bravery and cultural perceptiveness—as well as the injustices he faced.

Imagine an era in which police officers hung around clubs, waiting to hear what they thought of as offensive language—words that today seem nothing if not harmless. Detectives monitored Bruce’s act and arrested him after his sets, claiming it was because of his language: his use of the word cocksucker in San Francisco, schmuck in Philadelphia. But that was a distraction from the real offense. Paul Krassner, who helped Bruce edit How To Talk Dirty, tells me, “At the beginning, someone would yell out, ‘Lenny, you’re really funny!’ But a couple of years later, they would scream, ‘Lenny, you’re honest!’” There was no legal charge for honesty, as brutal and hilarious as it may be, so obscenity had to do. Bruce’s aptitude for revealing society’s hypocrisies (as well as his penchant for getting busted for drugs) kept him in courtrooms from 1961 until his far too early death in 1965.

To read How to Talk Dirty today is to “look at the lab notes of comedy,” says Black, who wrote the preface to the new edition. Astonishingly clear connections can be drawn between Bruce’s work and the celebrated material of every decade since. Sam Kinison’s routine about a pissed-off Jesus returning is a grandchild of Bruce’s bit on Jesus and Moses conversing in St. Patrick’s Cathedral. Bruce’s prophecy that marijuana will be legalized by the “pot-smoking law students” who will one day be congressmen echoes in Chris Rock’s bit about the hypocrisy of government drug policy. (“They don’t want you to use your drugs…they want you to use their drugs!”) And the Key & Peele sketch lampooning white America’s attempts to be cool with black culture—the white bro forcing Jordan Peele’s attention to his Tribe Called Quest T-shirt—is a direct descendant of Bruce’s “How to Relax Your Colored Friends at Parties.” This isn’t to say these comedians are consciously riffing off of Lenny Bruce’s act; it’s to say that he created a style and sensibility that’s still thriving five decades later.

Of course, that cultural perceptiveness, saluted by comics in every generation since, came at a high price.

On this anniversary of Bruce’s death, one vulnerable line in How to Talk Dirty stands out: “I know (and it disturbs me greatly) that soon I will be out of touch.… There’s nothing sadder than an old hipster,” Bruce laments. But there is something much sadder: a hipster who was so deeply in touch that authorities couldn’t stand to let him speak freely. Lucky for us, he wrote a few things down.

Jeremy Elias is a freelance writer living in New York City. His work has been published in Esquire, The Atlantic, Tablet magazine, Vice and more.