The original album was recorded and produced by Owsley "Bear" Stanley, the Dead's then-soundman, who chose his favorite tracks.

He compiled it as a tribute of sorts to Ron "Pigpen" McKernan, the band's original keyboard player and blues aficionado, who died during the production of the release.

"[6][a] Though it was something of a contractual obligation, as the band were trying to finish the terms of their recording contract and end their association with Warner Bros., it was compiled as the first volume of either a two-volume set or a series.

The official title, History of the Grateful Dead, Volume One, reflects its unofficial intent as a tribute and send-off to Pigpen.

"[8] Side one consists of acoustic performances by McKernan, Jerry Garcia, and Bob Weir on country blues and folk covers, with one original from Workingman's Dead.

The second side features the entire electric band on blues covers "Smokestack Lightning" by Howlin' Wolf, and "Hard to Handle" by Otis Redding.

The parenthetical "Bear's Choice" of the title prevented confusion with a homonymous, non-contractual album, in retail bins at the time.

[9] The front cover also has the first appearance of the "Good Old Grateful Dead" epithet, circling the "Lightning Skull" graphic.

The contemporaneous bonus tracks include another one from the February 13, 1970 concert, and three from a week earlier at the Fillmore West in San Francisco.