Last night, the world received the news that Hugh Hefner, the iconic founder of Playboy, had passed away at the age of 91. For decades, Hefner himself was both the leader and the embodiment of the lavish, socially and sexually forward-thinking lifestyle that the magazine purveyed, all the while building the magazine into a massive media and entertainment industry giant.

Hef’s overarching legacy will be predominantly classified by scantily clad women in bunny outfits, the legendary Playboy Mansion and, of course, Playboy Magazine. But amidst the Playboy TVs and the Girls Next Door reality shows and the like, many may gloss over one of Hefner’s most substantive additions to the canon of American culture: his short-lived late-60’s TV show, Playboy After Dark. In a similar concept to his original TV show, Playboy’s Penthouse, each episode of After Dark was set at a “typical” party at Hefner’s house, complete with celebrities and Playboy Playmates who would then chat with their hose and perform for the “party’s” guests.

The Grateful Dead Once Dosed The Crew Of ‘Playboy After Dark’ With LSD

While the (actual) legendary parties at Hef’s house were less about the music than the general air of debauchery and permissiveness, Playboy After Dark managed to pack a truly incredible and diverse list of musicians into its short run of episodes, including The Grateful Dead, James Brown, Joe Cocker, Ike & Tina Turner, Sammy Davis Jr., Harty Nilsson, Deep Purple, Three Dog Night, Steppenwolf, Grand Funk Railroad, Steppenwolf, and more. The musicians would chat with Hef, perform a couple tunes, and join the party–some more-so than others, as The Grateful Dead’s Bill Kreutzmann would tell you. At that point in time, the LA soundstage on which the “Hefner’s place” set was built was not outfitted for live music performances, so many of the full-band appearances were mimed. But technical limitations aside, by consistently attracting such a star-studded roster of musicians to his show, Hefner made Playboy After Dark a beloved and lasting relic of popular music and culture at the end of the 1960’s that still feels just as entertaining more than 40 years later.

Today, in Hefner’s memory, take a look back at some of the most memorable musical guests on Playboy After Dark during the show’s year(ish)-long run from early 1969-1970:

James Brown (1969) – “If I Ruled The World”; “Say It Loud” (via YouTube user ishouldwinagrammy):

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James Brown (1970) – “Georgia On My Mind”; “By The Time I Get To Phoenix” (via YouTube user ishouldwinagrammy):

Sammy Davis Jr./Jerry Lewis – “Rock-A-Bye Your Baby” (via YouTube user Elmo Parsley):

Steppenwolf – “Berry Rides Again” & more (via YouTube user Pete Cosmic)

Deep Purple – “Hush” (via YouTube user AudioFidelity)

Grand Funk Railroad – “Mr. Limousine Driver”; “Please Don’t Worry” (via YouTube user T.J. Ash)

Rest in peace, Hef–There will never be another guy quite like you.