The dangers of hipness by proxy … or Lenny Bruce “hanging out” with Hugh Hefner on “Playboy’s Penthouse” Oct 24, 1959

By now, most people know the story about how a certain uptight Midwestern uber-nerd of the 1950s … Hugh Hefner … rebranded himself as a suave, hip (wait for it …) “playboy” and turned publishing and American culture on its head.  And all kidding aside, “Playboy” magazine was a remarkable accomplishment.  In a post World War II era where 10% of people interviewed thought an unmarried person could be happy (80%  believing that bacherlors were “sick, neurotic, and immoral”), Hefner made being a bachelor “cool,” selling an alternative image of unlimited sex and pleasure to a nation shackled to a notion that suburban domesticity was the ideal.  In addition, Hefner craftily classed up his magazine with important writers and thinkers of the day, not only giving his so-called “dirty” magazine a sense of sophistication, but exposing mainstream America to Jack Kerouac, Allen Ginsberg, Gregory Corso, John Steinbeck, James Jones, W. Somerset Maugham, Norman Mailer, Philip Roth, and John Updike.  Of course, Hefner was not the first person to expose America to these literary giants, but by placing their writing among the nude pictorials, mainstream Americans arguably became more exposed to these works based on their placement in “Playboy.”

Yet at the same time, Hefner was actually more in line with the conservative 1950s than his image projected at the time.  Per Mike Edision, in his brilliant and entertaining look at America’s pioneering print pornographers “Dirty Dirty Dirty,” who observed: “Despite his protests, (Hefner) was the very definition of bourgeois.  He gave lip service to mainstream American values, but he advocated the conspicuous consumption that was at the heart of the nation’s pride in its hard-won prosperity.  In this case it was sports cars, not station wagons; stereo components, not washer-dryers – but it was constructed with the same vapid building blocks of materialism and peddled by the same choice Mammon who pushed aluminum siding and riding mowers. Hef was creating a new playbook for the single male, but it was still based on the old caste system of He with the Coolest Stuff Wins.”  In other words, Hefner was one of the most successful marketers of consumerism as rebellion.

So who better to drop a turd into Hefner’s impeccably created martini than the then-current king of “sick humor” Lenny Bruce. In this late 1950s television version of the Playboy Lifestyle (“Playboy Penthouse’), Hefner tries to navigate a manufactured urban penthouse set in tuxedo, selling the Playboy philosophy while still looking a little uncomfortable in the role.  While Hefner was a definite fan and supporter of Bruce’s over the years, Bruce was obviously invited to this televised shindig to provide a some reflected hip glory on Hefner.  And Bruce isn’t having any of it, brutally identifying the truth behind the Playboy philosophy “Playboy is very chic, and you can say sophisticated, and the magazine is filled with sports coats, about your views about sports cars, and I am glad you have one, ’cause you don’t care about the people who don’t have money … they can wait for their own magazine. ‘Field and Stream’? … The Playmate has a duck in her mouth.”  Hefner gamely attempts to take it on the chin, though he’s obviously very uneasy about Bruce calling him out.  A very funny and subversive American pop culture moment.

Oh, and again, please read Mike Edison’s “Dirty, Dirty, Dirty,” a ridiculously entertaining look at not only Hefner, but Bob Guccione, Larry Flynt, and Al Goldstein.

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“Lenny Bruce Tries to do a Clean Show” from “Lenny” (1974) dir. Bob Fosse

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From Bob Fosse’s terrific, but sad biopic of the late comedian Lenny Bruce comes this scene where Lenny (played by Dustin Hoffman) attempts to do a stand-up routine without saying a certain word that got him arrested a few nights earlier. As he points out, the routine is far dirtier without the bad word than with the word. A funny and clever way to make a very crucial point … that the truth, as ugly as it may be at times, is far less offensive than the lie that’s often used to mask the truth.

Doug Stanhope on Artists “Dying too Young”

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From Doug Stanhope’s unbelievably awesome comedy special “No Refunds” from 2007 is his take on artists who people think died too young. Stanhope’s comments on Jimi Hendrix and Lenny Bruce may seem sacrilegious … but it doesn’t make them any less true. Not safe for work or little ones by any stretch of the imagination.