By the summer of 1987, the Grateful Dead were riding an unlikely second wave of mass popularity, their fanbase swelling well beyond the faithful who had followed them through the leaner years of the early '80s. "In the Dark" was about to drop in July, and with it "Touch of Grey" — the band's first and only Top 40 hit — would introduce a whole new generation to the circus. But in June, right on the cusp of that breakthrough, the Dead were still very much a touring band doing what they'd always done: playing outdoor shows to devoted crowds in the warmth of the California summer. Brent Mydland was now firmly established as the band's keyboardist, no longer the newcomer who replaced Keith Godchaux back in 1979. He'd grown into the role with a soulful, blues-drenched ferocity that gave this era its particular muscle, and his voice — raw and aching — added a dimension that had been missing for years. The Ventura County Fairgrounds sits just up the coast from Los Angeles, and shows at outdoor fairgrounds like this one had a breezy, loosened-up character that could bring out some of the band's most relaxed and exploratory playing. Without the cavernous reverb of an arena or the sacred electricity of a Madison Square Garden run, fairground gigs often felt close and communal — closer to the old days than many fans might have expected from a band now filling stadiums.
The Pacific air, the open sky, the smell of the coast: it's the kind of setting that puts musicians at ease. The fragment we have from this show — "Around & Around" sliding into "Jack Straw" and then into "Mama Tried" — suggests a first set with some country twang and classic rock and roll swagger built right into its bones. Chuck Berry's "Around & Around" was one of those perennial Dead vehicles that Garcia and company could rev up or lean back on depending on the night, and when it flows into the tight acoustic pocket of "Jack Straw," you're hearing the band navigate one of those natural seams between loose joy and tight precision. "Mama Tried" in this sequence has the feel of a short, punchy declaration — Merle Haggard by way of Marin County. The recording source for this date is worth checking before you queue it up, as 1987 outdoor shows vary widely from crisp soundboards to warm but diffuse audience tapes. Whatever the source, settle in and let the loose California energy of this pre-fame-wave moment wash over you — this is the Dead at a hinge point in history, still comfortable in their own skin.