Speculating on how an 85-year-old Lenny Bruce would be celebrating his birthday today is as fun as it is pointless.
But it’s pretty easy to guess that edgy comedy’s patron saint would not have been able to stretch out casually on TV for 25 minutes in conversation with a legendary publisher and lifestyle creator like the Hef.
That’s what happened in 1959 on the first episode of Playboy’s Penthouse, Hugh Hefner’s first foray into TV, which broadcast from WBKB in his Chicago hometown. This was the first mass-market exposure of the erstwhile club-bound Bruce, and its high-end hepness set the tone for the show’s two-season run, which featured a ton of figures in the jazz culture scene.
Of course, the dynamic between the eloquent snapping-and-riffing Long Islander Bruce and the perennially modest Midwestern Hefner is classic as the comedian covers topics like “sick” comedy, nose-blowing, Steve Allen, network censorship, tattoos & Jews, decency wackos, Lou Costello, integration, stereotypes, medicine and more.