Lenny Bruce was a stand-up comedian with a knack for political satire and “blue comedy” that could even make an adult movie star blush. More often than not, his free-wheeling style of stand-up landed him in trouble with the law—and, worse yet, his wife.
But beneath the veneer of this carefree comedian, lurked a deeply troubled individual.
1. He Was Forever Young
Lenny Bruce was destined to be as reckless with his life as he was with his comedy. On one chilling occasion, while referencing his struggle with addiction, he said, "I'll die young, but it's like kissing God". Sadly, those words would become more prophetic than he realized.
Each chapter of his life proved more harrowing than the last—and it all began with his childhood.
2. His Father Was Never Home
Born Leonard Alfred Schneider, Lenny Bruce would go on to become one of the most influential people in stand-up comedy. But there was nothing funny about his start in life.
Bruce’s father was Myron Schenider, a shoe clerk who was rarely, if ever, home. And his mother, Sally Marr, was an aspiring entertainer and comedian herself. However, his childhood was anything but stable.
Looking for Lenny (2011), Borderline Films
3. He Barely Survived School
With an absent father and a mother in show business, Bruce spent the early years of childhood bouncing between relatives. Suffice it to say, he received a somewhat spotty education.
“I won’t say ours was a tough school,” Bruce later said in one of his stand-up bits, “but we had our own coroner. We used to write songs like, ‘What I'm going to do if I grow up’”. He may have made light of it all, but the truth was that Bruce had it rough.
4. His Mother Raised Him
Around the time Bruce was five years old, a big change ripped his family apart: His mother divorced his father.
The reasons for the divorce are unclear but, from then on, she worked as a waitress to support herself and Bruce while still making her way as a comedian. Little did Sally Marr know, her career choice would have a huge influence on her son—and ultimately—the future of comedy.
Looking for Lenny (2011), Borderline Films
5. He Learned From The Best
Marr met with moderate success in her own career as a comedian and later worked unofficially as a talent scout. And she knew that the best talent was right under her nose.
In a 1989 interview, Marr said, “People are always saying that everything in comedy stems from Lenny—that everything touches him. What can I tell you? He took after me!”
However, Bruce's road to stardom wasn't exactly a straight shot.
Looking for Lenny (2011), Borderline Films
6. He Was A Farm Boy
Despite his mother’s influence, Bruce didn’t immediately think of comedy as a career. Instead, he found work on a farm and then joined the United States Navy in 1942 at just 16 years of age.
For the most part, his service with the armed forces was honorable. Until Bruce’s true colors came out—his rainbow colors, that is.
Looking for Lenny (2011), Borderline Films
7. He Was A Real Drag
One day in May of 1945, Bruce embraced his show business talents and put on a show for his shipmates…in drag. While the comedic performance had his fellow crewmen rolling around the ship’s deck in laughter, his supervising officers were not so impressed.
In fact, they didn’t think that Bruce was joking at all. And maybe he wasn’t.
Looking for Lenny (2011), Borderline Films
8. He Made A Shocking Confession
Following Bruce’s breakout performance, he made a shocking announcement to his superiors.
In a written letter, the novice comedian confessed that he was “normal in all aspects” except for one. Bruce wrote that he was “attracted physically to a few of the fellows [shipmates]” one of whom he said he “kissed a lot”. It seemed like a serious problem.
Looking for Lenny (2011), Borderline Films
9. He Was Very Gay
Bruce’s written confession went straight up the chain of command. The navy medical officer testified that Bruce had even admitted to “suppressing [gay] tendencies” and that “the desire [was] becoming stronger”.
In fact, concern over Bruce’s orientation became a top priority for commanding navy officers. But Bruce was already a lost cause.
Looking for Lenny (2011), Borderline Films
10. He Was Dishonorable
After much consideration, the navy brass decided to send Bruce for “neuro-psychiatric consultation” in light of his “tremendous amount of [gay] drive with some mild amount of overt [gay] tendencies”. Eventually, the navy decided that there was no hope for Bruce and he was dishonorably discharged. But that wasn’t the punchline.
Looking for Lenny (2011), Borderline Films
11. He Was No “Sissy”
Bruce appealed his dishonorable discharge. He was hoping to have it upgraded to an honorable discharge “by reason of unsuitability for the naval service”. In his appeal, Bruce cited his active combat roles and argued, “I think no one would accuse me of having behaved like a ‘sissy’”.
However, down the road, Bruce decided to change his entire story.
Looking for Lenny (2011), Borderline Films
12. He Pulled Off One Of The Best Pranks
Decades later, in his memoir, Bruce gave up the ruse. He confessed that the entire thing had been a practical joke. He had faked having gay tendencies and confessed to making the whole thing up so that he could get out of the navy to pursue a career in comedy. Unfortunately for Bruce, more laughs only meant more trouble.
Looking for Lenny (2011), Borderline Films
13. He Was A Stand-up, Not A Stand-out
After the navy, Bruce spent a little time in California before settling down in New York City to pursue his career in comedy. But the laughs in New York’s comedy clubs didn’t come as easily as they had on the navy ship and he struggled to stand out from the other acts on stage. That is, until his mother gave him the leg up that he needed.
The Marvelous Mrs Maisel (2017-), Amazon Studios
14. He Was Paid In Pasta
As a struggling stand-up comedian, it was hard for Bruce to pay the bills—unless his debt collectors accepted pasta as payment. Bruce landed his first paid gig in 1947, shortly after changing his stage name from Lenny Marsalle to the now iconic name Lenny Bruce. For his gig, however, he received a paltry $12 and a spaghetti dinner.
However, despite his meager beginnings, Bruce wasn't about to throw in the towel.
The Marvelous Mrs Maisel (2017-), Amazon Studios
15. He Found An Audience
Over the next couple of years, Bruce sharpened his comedic chops alongside the likes of Joe Ancis, Joe Maini, Lord Buckley, and, of course, his own mother. Slowly, he gained a following in New York City, getting laughs for his ribald ad-libs and scathing political satire. He had no clue that his life was about to change in a big way.
The Marvelous Mrs Maisel (2017-), Amazon Studios
16. He Fell Madly In Love
In 1951, Bruce met and married Honey Harlow, a top-notch burlesque dancer from Manila, Arkansas. There aren’t many details about how they met but it’s safe to assume that it was likely at a club where Bruce was performing.
However, the details that we do know about this romance make it sound like Bruce and Harlow were the Bonnie and Clyde of comedy.
The Marvelous Mrs Maisel (2017-), Amazon Studios
17. He Had To Make Money Fast
We can’t say for sure it was true love between Bruce and Harlow but their romance was definitely full of passion (and narcotics). Bruce was also determined to make enough money so that Harlow could retire from her life as an exotic dancer. And so, over the course of their marriage, he came up with a few get-rich-quick schemes.
The Marvelous Mrs Maisel (2017-), Amazon Studios
18. He Joined The Clergy
Shortly after he married Harlow, Bruce put one of his ill-conceived schemes into motion. Posing as a laundry man, Bruce borrowed (on a permanent basis) a priest’s clerical collar and a number of clergy shirts. What business did a newlywed comedian have with priest’s clothing? Funny business, of course.
19. He Had A Charitable Heart
Dressed in his “borrowed” clothing, Bruce went around Florida, impersonating a priest. The comedian-turned-con man claimed to be collecting donations for a leper colony in British Guiana (or what is now Guyana).
He even went to the trouble of setting up a real charity called the Brother Mathias Foundation. But of course, this was just another key aspect of his nefarious plan.
The Marvelous Mrs Maisel (2017-), Amazon Studios
20. He Pocketed The Proceeds
In just three weeks, Bruce managed to collect $8,000 in donations for his Brother Mathias Foundation charity. But he wasn’t exactly doing God’s work. In his autobiography How to Talk Dirty and Influence People, Bruce made a horrifying confession.
He said that he kept the majority of the money for himself. Only $2,500 actually made it to the leper colony. But here's where it gets messy.
The Marvelous Mrs Maisel (2017-), Amazon Studios
21. He Fooled The Church
Just like with the navy, the New York courts had a hard time figuring out if Bruce’s leper colony scheme was authentic or just an elaborate hoax. As such, the comedian con man didn’t face serious repercussions for his acts given that his charity was real. Even church officials were unable to prove that Bruce was, in fact, an impostor.
Getting out of this mess relatively unscathed, Bruce took his skewed morality and decided to begin a new chapter.
The Marvelous Mrs Maisel (2017-), Amazon Studios
22. He Skipped Town
None of Bruce’s money-making schemes panned out so, in 1953, he and Harlow packed their bags and headed to Los Angeles. But Bruce still dreamed of making enough money to get Harlow off of the burlesque stage. In fact, he was determined to make a legitimate movie star out of his wife.
But the Hollywood crowd would prove to be a tough one.
The Marvelous Mrs Maisel (2017-), Amazon Studios
23. He Ran A Dance Hall Racket
Bruce and Harlow starred together in 1953’s Dance Hall Racket, a mafia-themed screenplay that Bruce had written himself. Sadly, the only laughs that the film garnered were snickers of derision.
Both audiences and critics panned the film and it flopped at the box office. If anything, that only motivated Bruce to try even harder.
Looking for Lenny (2011), Borderline Films
24. He Was A Terrible Writer
Bruce tried a few other screenplays. Most notably, The Rocket Man and Dream Follies both in 1954. But the strictures of scriptwriting and the tight censorship rules of 1950s Hollywood made film a tough avenue for a raunchy comedian and a burlesque dancer. For Bruce, the writing was on the wall. It was stand-up or nothing.
Looking for Lenny (2011), Borderline Films
25. He Was At Home In The Gutter
Throughout his brief—and highly unsuccessful—film career, Bruce continued working as a stand-up comedian. As the master of ceremonies, he introduced burlesque dancers before they came on stage and tried out his new material on the, how should we say, “eager” crowds. And there, in the seedy underbelly of society, Bruce found his audience.
The Marvelous Mrs Maisel (2017-), Amazon Studios
26. He Was The “Lowest Of The Low”
Bruce’s biographer wrote about his time working at the burlesque clubs around Los Angeles, saying that it was “precisely at the moment when he sank to the bottom of the barrel and started working the places that were the lowest of the low” that he broke free and became himself.
That’s where Bruce developed his unique style of comedy.
The Marvelous Mrs Maisel (2017-), Amazon Studios
27. He Had No Inhibitions
Bruce’s biographer went on to say, “all the restraints and inhibitions and disabilities that formerly had kept him just mediocre and began to blow with a spontaneous freedom and resourcefulness that resembled the style and inspiration of his new friends and admirers, the jazz musicians of the modernist school”. And Bruce was breaking out in more ways than one.
The Marvelous Mrs Maisel (2017-), Amazon Studios
28. His Marriage Was Falling Apart
Even though Bruce had found his stride as a comedian, his personal life was falling apart. In 1955, he and his wife, Harlow, welcomed a baby girl into their family. But their marriage was far from stable.
The following year, in 1956, the couple went their separate ways. At least, that’s how it seemed. For like…two weeks.
Looking for Lenny (2011), Borderline Films
29. He Had A Delayed Honeymoon
Shortly after their split, the comedian and burlesque dancer were back together—personally and professionally. On a much-delayed working honeymoon, they went on a trip to Honolulu together to go on a tour of nightclubs. They even brought their little baby, Kitty, along with them. But the apparently happy family wouldn’t be leaving intact.
The Marvelous Mrs Maisel (2017-), Amazon Studios
30. He Abandoned His Wife
While in Honolulu, Harlow picked up a charge for possession of illicit substances. The conditions of her release stipulated that she couldn’t leave Honolulu. And Bruce saw that as the perfect opportunity to ditch his on-again, off-again wife.
With the one-year-old Kitty in tow, Bruce did his wife dirty and headed back to the mainland without her.
The Marvelous Mrs Maisel (2017-), Amazon Studios
31. He Plotted His Wife’s Incarceration
Back in Honolulu, Harlow was eventually found guilty and sentenced to two years in a federal lock-up. But the truth behind Bruce’s betrayal was even worse than abandonment.
Decades later, Harlow revealed that Bruce was the one who had turned her in to the authorities in the first place. But that's not all.
Looking for Lenny (2011), Borderline Films
32. He Had Another Woman In Sight
Bruce might have had another reason for abandoning Harlow in Honolulu. There was no doubt that, despite his professional success, his marriage was on the rocks. He had also failed to turn Harlow into a legitimate Hollywood star. From the looks of it, Bruce had shifted his romantic attention to another woman.
33. He Was A Cheater
Sometime in the 1950s, Bruce met the jazz singer Annie Ross and started carrying on an affair with her. Once again, Bruce managed to keep the more sordid details of their relationship out of the historical record. But there’s almost no doubt that he was cheating on Harlow with Ross, perhaps at the same time that he betrayed his wife.
However, Bruce proved that he could be a twisted lover no matter the woman he was with.
The Marvelous Mrs Maisel (2017-), Amazon Studios
34. He Was “Lovesick”
Bruce and Annie Ross were definitely lovers at some point. However, true to his comic lifestyle, Bruce had a funny way of showing his affection for Ross.
Ross later said about her fling with Bruce, “He was very special—and crazy. He would write ‘I love you’ on an [aeroplane] sick bag and mail it to me”. That certainly gives new meaning to the term “lovesick”.
The Marvelous Mrs Maisel (2017-), Amazon Studios
35. He Kind Of Started Saturday Night Live
Bruce was half of the original Saturday Night Live comedy sketch—kind of. He had a couple of appearances on the Patrice Munsel Show alongside his roommate and fellow comedian, Buddy Hackett.
The duo named their sketch appearances “Not Ready for Prime Time Players” decades before SNL borrowed the name, further cementing his influence on comedy.
36. He Was Too “Blue”
Pretty soon, Bruce’s raunchy style of humor was too much for sensitive audiences to bear. In 1957, for example, Bruce booked a prestigious spot at the Slate Brothers nightclub.
The audience didn’t care much for his ribald humor and he was promptly fired for what Variety called “blue material”. Funny enough, it only made Bruce even bigger.
Looking for Lenny (2011), Borderline Films
37. He Was Only Following God’s Lead
Despite the increasing backlash from the authorities against Bruce’s sense of humor, he remained unapologetic. In fact, as far as Bruce was concerned he was only doing God’s work with his bawdy, raunchy, and rebellious sense of humor.
“If God made the body, and the body is dirty,” Bruce quipped, “then the fault lies with the manufacturer”.
Looking for Lenny (2011), Borderline Films
38. He Kept Cracking Inappropriate Jokes
Following his ban from the Slate Brothers nightclub, Bruce went on to release a string of successful recordings of his comedy. His inappropriate, offensive, and honest humor made him as many fans as critics. And the more jokes that Bruce cracked, the more the authorities tried to crack the whip on him.
But they couldn’t get this stand-up to sit down.
Looking for Lenny (2011), Borderline Films
39. He Had To Stick To The Script
For the most part, studio executives prohibited Bruce from making television appearances for fear that he might go on one of his infamous rants. As such, whenever they did make exceptions, they insisted that he submit a script of his jokes beforehand. But, like any good comic, Bruce could never let the opportunity for a good joke go by—and it often got him into trouble.
40. He Embarrassed Elizabeth Taylor
Bruce was good friends with television personality and host, Steve Allen. At Allen’s behest, studio executives agreed to let Bruce make an appearance on his show.
Needless to say, Bruce took the opportunity to ad-lib a joke about Elizabeth Taylor’s recent marriage to Eddie Fisher, saying, “Will Elizabeth Taylor become bar mitzvahed?”
41. He Gave Generous Gifts
Even at the height of his success, Bruce kept up his antics and practical jokes. He once stole a bunch of books as a present for his friend, André Previn. But his reasoning was actually pretty sound. “If I had 90 bucks and spent it in order to get you a present, what would be a big deal in that?” Bruce asked.
“It wouldn't even make a dent in me! But to steal 'em for you—I'm already on parole, man, and if I had got caught, I would have gone back to [prison]. Now that's what I call giving you a present”.
42. He Was “Undesirable”
By the time the 1960s rolled around, Bruce’s stand-up comedy had earned him an international reputation, just not a very flattering one.
British authorities barred Bruce from entering the United Kingdom, claiming that he was an “undesirable alien”. But it was his troubles at home that Bruce was really starting to worry about.
The Marvelous Mrs Maisel (2017-), Amazon Studios
43. He Was Obscene
Between 1961 and 1964, Bruce found himself in cuffs multiple times facing obscenity charges for his comedy routines on stage.
Most of the time, the charges went away thanks to juries packed with fans of his material. But, in 1964, a New York jury wasn’t laughing with Bruce so much as they were laughing at him. Still, Bruce managed to steal the final laugh.
44. He Was Sentenced To Hard Labor
Despite a public petition and glowing testimony from celebrities like Woody Allen, Bob Dylan, and James Baldwin, the New York jury found Bruce guilty of obscenity.
Shocking as the verdict was, the sentence was even worse. The judge on the case sentenced Bruce to four months in a workhouse. But his real fate was even less funny.
45. He Had An Addiction Problem
For years, Bruce had suffered from addiction—and he wasn’t exactly picky about his poison. Records indicate that Bruce used many hard substances for years. All of those substances had taken their toll on Bruce’s health and, by the time of his sentencing, he was in no shape to spend four months in a workhouse.
46. He Was Full Of “Destruction And Despair”
Even though Bruce’s comedy was raunchy and playful, it had a somewhat sinister undertone. He once said, “All my humor is based on destruction and despair. If the whole world were tranquil, without disease and violence, I'd be standing in the breadline--right in [the] back of J Edgar Hoover”. For a funny man, the end of Bruce's story was no laughing matter.
47. He Overdosed On Life
Before Bruce even served a day of his sentence, he took his final bow. Authorities found Bruce’s lifeless body, unclothed, on the floor of the bathroom of his home in the Hollywood Hills.
According to photos taken at the scene, authorities found Bruce next to “a syringe and burned bottle cap nearby, along with various other narcotics paraphernalia”.
48. He Was A Comedy Evangelist
In delivering Bruce’s eulogy, the Reverend William Glenesk said, “He was in a sense an evangelist, on a street corner. He was a man—up tight against an artificial world…who shattered its facades, and its hypocrisy, and—if you will pardon the phrase which seems to become a cliche—he saw life as it is”. Albeit, with an odd sense of humor.
49. He Offed Christ, Apparently
Bruce wasn’t big on religion but he might have believed in God. “Every day people are straying away from the church and going back to God,” he said. But he never took his Jewish religion too seriously. “A lot of people say to me, ‘Why did you kill Christ?’. I dunno,” he joked. “It was one of those parties, got out of hand, you know”.
