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Somehow the Grateful Dead got invited to play Hugh Hefner’s “After Dark” show in January 1969. And I’m still trying to figure out how in hell Hefner and his producers felt the Dead were a group to have on the show, or how The Dead felt this was a scene they wanted to be involved with for even a minute or two. One thing does spring to mind: the band must have grinned like wolves at the thought of dosing every last one of the assembled. While Kesey had retired the bus, the Dead remained notorious for pranking any unsuspecting individual with a healthy dose of LSD in their drink of choice. The historical record is a bit unclear about whether or not the Dead got to Hef’s drink (though one story has Hefner toasted and telling Phil and Bill “I want to thank you for your special gift.” Enjoy the ride Hugh.) But it does seem that Owsley’s potent blend of acid was eye-dropped into the cups of many attendees, and if Jerry’s stoned banter and permanent grin are any indication, he was swimming in it. To take the weirdness up a notch, they start their set with a gorgeous version of their acoustic psych-chamber piece “Mountains of the Moon". Only ten or so times did this tune ever get played (all in 1969) -- and the Dead gift one to Playboy.



Oddly enough, this little engagement does let us in on the changing role of Ron "Pigpen" McKernan in the band's music. That’s Phil’s friend T.C. Constanten gracing the harpsichord. The Dead were in a definite transitional moment in early 1969, which is why Constanten rather than the band’s usual organist Pigpen is at the keys. Phil and Jerry had more adventurous sounds they were wanting to create, and not all members of the band were keeping up. Bob Weir wasn’t making much progress on the electric guitar and was asked to leave the band. As was Pigpen, who found it hard to create a space for his brand of blues and r&b in the increasingly psychedelic music. So Phil and Jerry brought in Constanten for some of the songs on 1969’s Aoxomoxoa. And it’s easy to see why, for Pigpen was just not the sort of player who was going to break out the harpischord to play a few delicate figures. But Constanten also took over organ duties, pressing Pigpen further to the edges of the band’s music. Skip ahead a little in that after dark night and we get a raucous “St. Stephen” with T.C. in the middle of it all on organ and Pigpen stranded in the corner with his congas, looking a little lost amidst the swirling riptide produced by the rest of the band.



Yet after the brief grumbling over his playing, he remained an essential member of the band’s live performances. Shows were inevitably capped by Pigpen mixing the rhythm & blues with Lord Buckley on triumphant versions of “Turn on your Lovelight.” After "St. Stephen" fades and Hugh says goodbye, we hear Pig and the band ripping through "Lovelight" for the dancing kings and queens, who look to be having the time of their lives on that LSD stuff. Pigpen outlasted T.C., who split amicably after a year, but Constanten’s brief tenure confirmed that the band’s music required a second keyboardist.