Hef makes it square to be hip

Look up “cool” in the way-back dictionary, and this is what you get:

“Playboy After Dark” -- Kennedy-era magazine magnate and bachelor icon Hugh Hefner hosting a “sophisticated weekly get-together of the people that we dig and who dig us.”

It’s only an aspirational, suburban cool -- not whatever the real thing might be. Playboy’s centerfold nudes are, after all, carefully airbrushed representations of the Girl Next Door. And their TV host is actually less urbane role-model than dorky neighbor.

Sorry, kids. Truth revealed: Hef’s hardly a hip swinger. More a desperately tone-deaf wanna-be. It would be sad -- if it wasn’t so hindsight hysterical.

Watch an at-sea Hef flounder throughout these three delirious, newly issued DVD discs (Morada Vision, $40), kicking off with two outings of his initial Chicago-based video soiree -- 1959’s black-and-white “Playboy’s Penthouse” -- before getting groovy with four installments of his color 1968 Hollywood revival, “Playboy After Dark.” Both were syndicated to local stations as late-night weekly peeps into the party lifestyle Playboy espoused when it emerged as a mainstream magazine touting the sexual revolution and all things “sophisticated.”

That’s a big red flag: All of Hef’s talk -- pipe in mouth, tux on body, babe(s) on arm -- is about his sophistication and the societal repression being battled within his Playboy pages. The more he harps on it, the less we buy it.

Hef and his nerdy editorial director, A.C. Spectorsky, host the first ‘50s episode of “Playboy’s Penthouse” with all the pizazz of paper towels, acting as earnestly “cool” as they can affect, surrounded by dishy dames and jazz cats downing drinks at a party in Hef’s Windy City bachelor pad (actually a TV studio).

Suddenly, “sick comic” guest Lenny Bruce hits ‘em like a fire hose, madly chatting up riffs on TV censorship, race, religion and other subjects too touchy for the era -- as Hef tightens up in horror/awe, his sitting-on-the-sectional body language practically screaming “get away from me.” Bruce is definitely cooking this night, and to our squirming host’s credit, he lets the rant run on for a fascinating 15 minutes.

After Bruce sets the tone, pert young author Rona Jaffe talks so sincerely about her sex-and-the-city novel “The Best of Everything” that pretentious Hef soon sinks in the swirl of candor.

Then Nat “King” Cole “drops in.” Then Ella Fitzgerald sings. They’re so relaxed, we have to step back this half-century later to realize how amazing their mere presence is. “Colored people,” as Bruce puts it politely (for the time), just didn’t party on TV with white folks. But here they do.

There are plenty of swingin’ sounds too around the piano that every bachelor penthouse supposedly has at its center. But the casual chat is what makes “Playboy’s Penthouse” such a time-capsule treat. Perhaps that very nakedness (heh heh) made the time’s TV overseers nervous.

By the time “Playboy After Dark” arrived a decade later, Hef has soooo gone Hollywood. Each of these four color episodes is packed with songs and comedy guests -- Sonny and Cher, Linda Ronstadt, Joe Cocker, Canned Heat, Mort Sahl, Jerry Lewis, even Bill Cosby, just hanging in the background mugging for lens time. Now it’s “a wild party,” a still-awkward Hef tells us, clinging to his tux even as return guest Sammy Davis Jr. arrives in bejeweled vest and gold medallions.

The party is no longer a casual get-together but a gotta-make-it “scene,” where braless blonds in micro-minis wander the burnt-orange decor looking drug-dazed.

Acts like the Ike and Tina Turner Revue go “wailin’ in the rumpus room” under psychedelic lights and a hi-fi wall with more useless gauges than “Star Trek.” There’s that suburban aspiration again. Doesn’t matter -- everyone’s so under the influence, they wouldn’t know what they’re seeing.

As mouthy young film critic Rex Reed slugs back another drink, he opines, “This is the first show I’ve ever been on in my life where I can plug a book and get zonked all at the same time.”

Thus, despite itself, “Playboy After Dark” provides a juicy peek at a moment in time, or two, and priceless footage of acts both hep and hip.

It’s also the unintentionally effective cautionary tale of an uptight upbringing morphing into I-will-too-be-cool desperation to reinvent oneself publicly. Pop-culture vultures will eat up these DVDs, but they might add a disclaimer: Don’t try this at home.