It wasn't all bunnies and glossy magazines with the late Hugh Hefner. In fact, his turn-of-the'70s foray into late-night television briefly served as a pipe-smoking, dinner-jacketed platform for classic rock.

The set for Playboy After Dark, which ran for 52 episodes between 1969-70, was built to resemble a mid-century cocktail party, complete with dancing guests and the clinking of highball glasses. Hefner had a penchant for jazz, but his musical guests also included Deep Purple, the Byrds, the Peter Green-era edition of Fleetwood Mac, Harry Nilsson, Grand Funk Railroad and Steppenwolf, among many others.

It wasn't always a comfortable mix. Outside of the musical performances – highlights of which include a psychedelic-costumed Deep Purple's charging through "Hush," Tina Turner transforming the Beatles' "Come Together" into a grease-popping groover, Fleetwood Mac's serrated version of "Rattlesnake Shake" – the show could be remarkably awkward, in particular when Hef interacted with band members.

On one episode, for instance, a tuxedo-clad Hefner discussed the current youth movement with an unkempt Jerry Garcia, clad in a scruffy serape. "Haight-Ashbury is just a place," he helpfully told Hefner. "It's just a street. It's not really the thing; it never was the thing that was going on. It was the thing people could talk about because it was easy to remember." That wasn't the only culture-clash moment. Canned Heat could be found discussing their record collection, while old-school stars of the day like Don Adams, Sid Caesar and Arte Johnson mill about. Activist Joan Baez couldn't have seemed more out of place performing "Hickory Wind."

Always more comfortable in the low-key setting of his Playboy mansion, Hefner tried to recreate a similar ambience in the CBS studios in Los Angeles – with the viewer as his guest of honor. The idea, he once said, was to create "a variety show that didn't seem like a variety show. There was a subjective camera that came up the elevator. You appeared to be a guest at a party at my apartment."

Still, Hefner could be a halting presence onscreen.

"He was terribly unsure of himself to the extent that we couldn’t get him to relax," Playboy After Dark writer Tony Hendra told the New York Post in 2017. "At the beginning of the show he would say, 'Good evening. I’m Hugh Hefner.' It always came out as, 'Good evening [snuffle]. 'I'm [snuffle] Hugh Hefner. I said, 'Maybe it would help if you pause a little bit between 'Good evening' and 'I'm Hugh Hefner.' I had to write a cue card that said, 'Good evening. [Pause.] I'm Hugh Hefner.'"

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Occasionally, bands like Three Dog Night and Iron Butterfly clearly lip synced their songs. Hefner also sometimes had trouble connecting with guests like Deep Purple's Jon Lord, who never took off his shades. Asked why the band left a communal home it once shared, Lord explained, "It was haunted." Hef seemed incredulous: "You really believe it was haunted?" "I know it was haunted," Lord replied. "I saw it with my own [long pause] glasses."

Perhaps that's why Playboy After Dark enjoyed a relatively short broadcasting run. It certainly wasn't the A-list group of guest stars. Watch closely, and you'll also find future Eagles co-founder Bernie Leadon backing up Linda Ronstadt on her cool-rocking cover of Hank Williams' "Lovesick Blues."

Of course, with this many rock stars hanging around, there were bound to be a few shenanigans. The Grateful Dead's 1969 performance was highlighted, onscreen at least, by performances of "Mountains of the Moon" and "St. Stephen." Behind the scenes, however, drummer Bill Kreutzmann said something else was going on.

"I start hearing the strangest things," the drummer said during a 2015 appearance on Conan O'Brien's late-night show. "'Camera 13, you're out of focus.' And then, 'Who's Mic 10? It's not on. I can't hear you.' I looked around and I started watching the people, and they're kind of loose. Then I had the strangest suspicion."

Turned out their sound engineer, Owsley "Bear" Stanley, slipped LSD into the Playboy After Dark crew's coffee – dosing the entire staff. "We did a couple of songs," Kruetzmann added, "then Phil Lesh and I were walking out" -- when they found a presumably stoned Hefner "frozen against the wall. I guess he got off on it."

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