Listen to the best Grateful Dead show from this day in history by clicking through below. Or search the complete collection of Dead recordings for shows from different dates, venues, and locations.

Playboy After Dark, CBS Studios
West Hollywood, California

On this day back in 1969, the Dead went on Hugh Hefner’s Playboy After Dark television program. The show opens with Jerry casually regaling the Playboy crowd as Hefner walks up and interrupts, right as Jerry was saying something about being “armed to the teeth with buck knives.” Hefner and Jerry go on talking for awhile, Hefner as stiff as Jerry is relaxed. In response to one of Hefner’s innane questions, Jerry goes off about how the two drummers “chase each other around," explaining, "It’s like the serpent that eats its own tail.” And, if you were to stand in between the two drum kits while they were playing, Jerry finishes, “they make big figure eights on their sides in your head.” Hefner, decisively freaked out...