I have previously written articles about how transformative the counterculture movement was to the entertainment industry and its effect on things like cinema, television and music in the 20th century. The world of comedy is no different, and at the center of mainstream humor’s transition from clean-cut suit-wearing men joking about their wives to Andy Samberg and Justin Timberlake joking about their “dick in a box” is the provocative Lenny Bruce, a man who many people credit as the comedian who opened the door for “filthy” humor, although he was so ahead of his time in many ways that the world was not quite ready for him when he entered show business, which may have been his biggest undoing.

Lenny Bruce was born in Mineola, New York on Long Island in 1925, the son of comedian and dancer Sally Marr who influenced Lenny from a young age. Before making it as a comedian in New York, Bruce had performed comedy for his fellow soldiers while he was in the U.S. Navy during World War II, which incidentally led to a dishonorable discharge. But things weren’t much easier for him after the war when he decided to pursue comedy as a career in NYC because that city was full of aspiring stars and Bruce found it difficult to stand out from everyone else. However a chance meeting with a man named Joe Ancis at a diner enlightened Bruce and opened his mind to a different style of humor that was more free-form, honest, stream-of-conscious and anti-establishment than average comedy. Something that was akin to the attitude of the Beat Generation of post-war America.

Bruce got laughs when he ad-libbed on stage and he became a regular on the stand-up comedy scene in Brooklyn during the forties, later becoming a guest on the radio show Arthur Godfrey’s Talent Scouts where he showed off his impression skills imitating movie stars like Humphrey Bogart and Edward G. Robinson.

In the fifties Bruce wrote and sometimes starred in movies, including Dance Hall Racket (1953) co-starring his mother Sally Marr and his wife Honey Harlow (who he met at a strip club in 1951), Dream Follies (1954) and sci-fi comedy The Rocket Man (1954), although these were all mostly unmemorable. Bruce had a lot more success on stage, especially at small venues and strip clubs like the one where he met his wife. At those places the stakes were lower so his comedy was allowed to be more loose and less mainstream, and this was the environment where he cultivated his raunchy sense of humor, joking about previously untouchable subjects which not only included stinging social commentary but also things like abortion and masturbation. He even exposed himself on stage while making a nudity joke, which was fine because many of the niche audiences who go to places like strip clubs laughed at that type of humor, but he did sometimes get fired from clubs for working more dirty than they wanted him to, and sometimes incidents like when Bruce got angry and cursed at audience members for being too loud during his routines caused club owners to chase him out. Things like this actually inspired the title of his first solo comedy album The Sick Humor of Lenny Bruce (1959) for Fantasy Records with whom Bruce made four original albums total.

Lenny Bruce had definitely achieved a certain level of notoriety in comedy. Nonetheless, he was often blacklisted from appearing on television for his reputation as a “sick” comic, although thankfully some celebrities were fans of his so people like Tonight Show host Steve Allen were able to give Bruce national exposure, albeit heavily monitored by Broadcast Standards and Practices. This was during the late fifties when his record The Sick Humor of Lenny Bruce took off and it was his most creative period. But he was still on the outskirts of mainstream fame because filthy humor was still shocking to most Americans in that decade.

A lot of old school comedians were especially opposed to Bruce’s filthy material and resented his popularity because they attributed it to his language rather than his talent, although Bruce was equally opposed to old school comedians who he criticized for being unoriginal and hacky. In the fifties, however, most people did not take Bruce’s side in that argument. His personality-driven anti-comedy approach was years ahead of its time before alternative comedy exploded in the seventies and eighties, an era when comedians would be more free in their personal expression and more widely accepted by audiences for doing so.

The sixties started out on a high note for Lenny Bruce when he performed at the famous Carnegie Hall in 1961 where he further pushed the envelope and challenged the standards of mainstream humor, but things would mostly go downhill from there and one of the main culprits was quite literally the fun police. While no one blinks an eye when comedians curse these days, back in the fifties and sixties these kinds of jokes were still unprecedented and shocking and America was far from mature enough to handle it, so how did this delicate little nation of Christians handle someone like Lenny Bruce? We arrested him, of course. Never mind what the Constitution says about free speech. He was also spied on by undercover cops, and sometimes even club owners got arrested for allowing him to go on stage in the first place. He even performed abroad in cities like London and Sydney at the height of his fame, but after leaving London he was barred from returning to the UK, and after leaving Sydney where he cursed at an audience member, he was criticized and shunned by Australia.

Although to be fair, Bruce was not exactly a saint. I would like him more if all he did was tell obscene jokes on stage, but he was also a severe drug addict and was part of a money laundering scheme at one point. His relationship with his wife (who he was constantly breaking up with and getting back together with) had soured to the point that they sometimes had drug-induced domestic incidents. They both got arrested for drug possession at various points, but his drug addiction caused him health problems as well as personal problems.

He did perform at a few clubs in the mid-sixties, including a show at San Francisco’s Basin Street West in 1965, but after becoming bankrupt by all his legal troubles he wasn’t as funny as he used to be and he was mostly just giving angry monologues about his legal troubles. By 1966 he had been blacklisted by nearly all clubs for fear of legal retaliation for harboring him. That was the year he died of a morphine overdose in the bathroom of his home in the Hollywood Hills.

Lenny Bruce was maybe the most radical stand-up comedian in history but he was far too unwilling to compromise his sensibilities and anti-authority spirit to make it big in Hollywood the way he could have. Although his influence on the world was huge. Two of the most popular comedians Richard Pryor and George Carlin both said he changed their lives. Carlin said Bruce changed the way he thought as a person in addition to being a comedic influence. He’s even the subject of countless homages, like when he was played by actors like Dustin Hoffman in Bob Fosse’s Lenny and Luke Kirby in the Prime Video series The Marvelous Mrs. Maisel, not to mention references in song by musicians like Bob Dylan (“Lenny Bruce was bad, he was the brother you never had”) and R.E.M. (“That’s great, it starts with an earthquake, birds, snakes and aeroplanes, and Lenny Bruce is not afraid”). These days when his style of comedy is a lot more common, Lenny Bruce is looked at more fondly by a lot more people, and his legacy in the world of comedy as the forefather of raunch, filth and lewdness is unmatched.