This  story is an attempt to have some fun with the character of Lenny Bruce, it is historically correct some, fictionalised in parts. It's a short story and there is not enough space to chronicle and detail all Lenny's arrest.       

Figaro Lucowski 

Jived to the moon on junk, you shlemiel, schemata, putz…  give me a rim shot, a sleazy drum roll as Cherry Soup takes it all off... real slow, live tits and ass, bang rat ta bing... slassssh. Baby did you cum? Did you cum good now? Lenny on stage a comic, schtick shocking everybody, the fat mayors, cops, the censors, the self righteous, God himself, the sleepers in their easy chairs, white-bread America dead by 9pm every night. Lenny the shark on the prowl looking for a fix at 2 am, brilliant performer and philosopher, the gad-fly bored shitless, poles-apart, scaring the be-Jesus out of middle America in the 50s, 60s, 70s, with off the chart shtick. Non-violent physically with a mouth like a time bomb that could go off any second. Saying things he wasn't supposed to say, pushing it, pressing taboo buttons, trying to get at the silly anal fuckers who controlled the script, the ones that decided what or what-not could be said in public on stage.
Lenny Bruce born Leonard Alfred Schneider, 1925 in Mineola, Long Island, he would become a Socratic one man revolution pouring pepper by the bottle on American white-bread.
From a fucked up family, sure, normality and business as usual never could have made a Lenny Bruce. By 5 Lenny was abandoned by his paternal family and passed around like a piece of meat from relative to relative.
 ….symbol clash schmaltz
AUTHOR'S ASIDE: It's 2 am, Hindemith on the radio is cranking me up, excuse the hyperbole. How many billionares, would give up everything they had to fight for the right of free speech? The right to say something dirty on stage or in a book or sing a dirty little song like "Louie Louie", " My Ding-a-Ling " or " Cock Sucker Blues ". Larry Flynt, publisher of Hustler Magazine, is the only one who has spent millions fighting for free speech, as Lenny Bruce did. Lenny ended up broke and shattered in the end, fighting.
Lenny at 13 stayed on the Dengler family farm on Long Island, four years with a surrogate family that gave him some stable white-bread home spun chutzpah, he had of balls by 17 and he joined the United States Navy in 1942. Lenny saw action and once he was out he became hip fast, hanging at strip clubs, the village and Times Square. Lenny never came close to a American Legion Hall or Memorial Day parade the rest of his life. 
Chew on this… Lenny was in the Navy for four years, he was HONORABLY DISCHARGED in 1946, for homosexuality. The Navy, the gayest place in the world, take the Neptune parties as they cross the Tropic of Cancer. Wearing coconut shell bras, put-on ladies' tits or Fijian grass skirts, wigs even. Sleeping in hammocks hung close together on long voyages. OH….any port in a storm hey sailor? Tokhes hanging out of hammocks, over-head swinging back and forth in rough waters at 2am..ahoy there matey?
Lenny served through World War Two, in the heat of  battle. The homosexual stamp on Bruce's discharge was a concession of Navy cluelessness, "This boy is a freak of nature, he doesn't think like the other good ole flag waving boys in the US Navy, we can't pigeon-hole him, he is odd, out there, so we will simply stamp his discharge papers, HOMOSEXUAL." The only category on the list that was odd enough to describe Lenny at the time.
When Lenny got out of the Navy in 1946 he was HIP, a radical concept for many at the time, particular for the Dengler family that raised him through high school. He showed at the family farm dressed in a Wave's uniform. He just got a little freaked out that's all. Lenny had a little taste of junk, fixed it, he started shooting up on Victory Day in New York City. The wholesome Dengler's wondering what happened to Lenny in the Navy? THIS ISN'T THE SWEET BOYCHIK LEO SCHNEIDER WE KNEW?
Lenny was living in New York in 1947. He started to spend time with his real mother Sadi Kitchenberg a comic, who had been on the road during his early life on the borscht belt. Away all the time she couldn't take care of him when he was young, throwing infant Lenny out like schemata in the bath water. Sadi was borscht belt comic royalty and off the chart. Lenny was born to be what he was, he and Sadie would sit in the kitchen at their apartment in Brooklyn and add lib, do comic routines for hours, Sadi recognised that Lenny was a comic genius and had talent.

There is a scene in the film "Lenny", Dustin Hoffman plays Bruce, not bad, not bad at all for a cowboy. Lenny and Sadi, Sadi playing straight, Lenny so fucking funny that he moves Sadi to tears, his Ma has to shut the comic monster down for a few minutes and locks him in the closet some, as a joke, to catch a breath.
By the 50s Lenny stood in as MC at the Victory Club on Ocean Parkway, a nightclub where his mother did gigs, his  first taste of show business. Later, performing in clubs such as Squires on Long Island, Clay Theater in Jersey and George's Corner in Greenwich Village for $2 an hour and cab fare home.
After doing bits performing comedy for the square weekend beats, suits during the week, Lenny became bored with yuk yuk green headed folk music lovers. Lenny was a junky, hip all the time, not just on the weekends. He started performing in east coast night clubs and strip joints. Lenny loved doing strip clubs because he was freer to improvise and could use language with less censorship.
Lenny met his first wife Honey Harlowe at a burlesque theater, a stripper who wore mama-san stiletto heals, asian style silk skirts with leg slits and button up collars. He really fell head over heals for Honey, both outcast by the late fifties! It was co-dependent love at first bite. Two adrift, out of place mentsh falling for each other out of desperation on junky strip club desolation row. Yes, Honey was a shekse (not Jewish), which made her more alluring to Lenny, he was bored by women he could control. Honey would cause Lenny allot of headaches in his life.
Lenny didn't like Honey stripping after they were married. She was curious when Lenny would fix, so Lenny fixed Honey one day wanting to stop her from stripping, to get control over her. It worked, Honey stopped stripping, but the couple needed to come up with more money to support their habits.
One of Lenny's early bust, which got him publicity was the Brother Mathias Foundation bit, a scam for junk money. Lenny put on a clergy collar and went door to door collecting money for lepers. He made a whopping eight grand in a 3 weeks. Eventually he got busted and gave two grand to lepers to get off the hook.
Lenny and Honey moved to LA in the sixties, his comedy bits were becoming known and Hollywood people were starting to go to his shows, narcs and the obscenity police were starting to attend his gigs on a regular basis too. Lenny began to move away from doing bits at strip joints and play more "straight clubs". He got his first big break Ann's Club in San Francisco performing  for $750 a week, allot was spent on junk, , but they were staying at first rate hotels after years on the burlesque belt living in dumps.
Hugh Hefner gave Lenny the introductions that would make him famous in 1959. Hefner was hip literati, Playboy  published the work of the the most gifted authors of the time. On the Playboy band-wagon Lenny was contracted to write comedy and do comedic albums for Twentieth Century Fox. The poker game of life and fame is only won by a hand-few, Lenny was on his way. His LIVE performances in clubs were now being recorded and sold on vinyl. He went on TV, the Steve Allen show, Playboy After Hours and the Arthur Godfrey show. 
(Lenny and Arthur Godfrey two people who couldn't have had less in common, like Hunter S. Thompson meeting Nixon, much more toxic and rattlesnake-like, unpredictable and funny). 
Lenny wowed and blew the minds of TV viewers. FOR FUCK SAKE,  heroin flowing in his blood stream and juicing out through speech patterns and movement while on TV. Lenny and Ray Charles, White-bread Americas first 'taste' of jazzed and jones freak-hood on TV.  Sixties junkies on the TV scene held in check by Ed Sullivan and network suits. Scenes like Jamie Fox playing Ray in Atlantic Studios weaving from side to side and itching his shoulders every 30 seconds could hardly be played out on sixties TV. Lenny never kicked and never tried too, Ray kicked, Lenny the rugged individualist, the rodeo clown with a mouth like a raging bull that resonated across the globe, he loved it on the edge, that's what kept him junked and on stage.
Lenny's obsenity bust were what counted historically and were the crux of his insurrection. His bits in clubs, his poetic on the edge use of humor as provocateur, philosophic self dialogue, tweaking and pushing the buttons of obscenity laws of the sixties, seventies and even today are what made Lenny Bruce the revolutionary he was. 
Joe Schlock of the late 60s, doing the trendy thing going to a club to watch Lenny Bruce do his bits, wondering what the fuck? Unable to understand the political references to his court cases for obscenity, the historical  relevance going over their heads. Lenny not pandering, junked up on stage, fixed on the political bits, which were humorless, not giving a shit. 
The film about Lenny's life with Dustin Hoffman was full of watered down bits so movie goers didn't have to work to hard mentally to get the drift of the genius pontificating. But if you have access to his last work in the library or record, wherever and take the time to listen, you will see, Lenny Bruce, Socrates doing his job.
"In March of 1962 his first obscenity trial in San Francisco is held. He is charged with violating Section 311.6 of the Penal code of the state of California, which provides: Every person who knowingly sings or speaks any obscene song, ballad, or any other words in a public place is guilty of a misdemeanor."
October 6, 1962, he is arrested for possession of junk.
Later that October, Lenny is banned from Australia, FOR SAYING FUCK? What the fuck? ( OZZY puritans, maven motha fuckers who fed cyanide to the Aborigine killing them by the thousands, shocked to hear the word FUCK, go figure?)

In December Lenny is arrested at the Gate of Horn club in Chicago for obscenity. The language dicks, you know, the fat square heads with no necks in trench coats, wearing size 12 Wingtips were there waiting for the bad boy to say ,fuck, cunt, pussy. LENNY WITH THE BIGGEST PAIR OF BALLS IN THE 20TH CENTURY OBLIGES AND OF COURSE COULDN'T RESIST, HE WAS ARRESTED.
"Seventy prominent American figures including Gore Vidal, Elizabeth Taylor, Arthur Miller, Woody Allen and Paul Newman sign a petition in support of Lenny Bruce".
Lenny had a number of court cases going on for dope and obscenity in Illinois, New York and California. He continued to perform in clubs, dodging  hard time by appealing and jumping bail from state to state. His legal fees caused him to file for bankruptcy in October 1962. Hugh Hefner and Playboy continued to back Lenny and published his book 'How to Win Friends and Talk Dirty' on Playboy Press.
Lenny the fucking giant bull, you gotta love him for never giving up and selling out his principles, his passion for freedom of speech and freedom to do dope if he wanted to. Always pushing it to the limits, with little regards for his personal health or lifestyle.
On July 25, 1966, Lenny did a show with Frank Zappa and the Mothers of Invention at the Fillmore East in San Francisco. It was as though the times had finally caught up with him, maybe. Sick, overweight, broke and facing jail time on a shit load of court cases. Lenny siting back stage on an old sofa next to an antique bedroom light on a small table, draped by a red curtain, smoking menthol cigarettes, bored by it all, seeing through the hippies, many who didn't know who he was, most dosing on LSD, somewhere else. Lenny Bruce  wanting to go home to fix and lay in bed, listen to jazz.  
Only a week later Lenny was back in LA, alone in his suburban spa style modern house. Even with the heart of a rodeo bull, Lenny's body finally gave in to heroin and cigarettes, he died of an overdose.

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