By the summer of 1987, the Grateful Dead were riding one of the more unexpected cultural waves of their career. "In the Dark" was about to drop in July, bringing "Touch of Grey" to MTV and introducing a whole new generation to the band — but on this late June night at Alpine Valley, none of that had happened yet. The crowd packed into the natural amphitheater outside East Troy, Wisconsin was still largely the devoted faithful, and the band was in the thick of a summer tour that felt both expansive and energized. Brent Mydland, now eight years into his tenure as keyboardist, had fully grown into the role; his gospel-inflected Hammond work and powerful voice had become essential to the band's texture, and his chemistry with Garcia, Weir, and the rhythm section was as locked-in as it would ever be. This is the Dead at a genuinely underrated moment — not the mythologized peak of '77, but a living, breathing outfit with something to prove. Alpine Valley itself deserves a word. The hillside shed southeast of Milwaukee was a beloved stop on the Dead's touring circuit throughout the '80s and into the '90s, capable of holding enormous crowds in an outdoor setting that balanced festival-scale energy with genuine warmth. Wisconsin Dead fans were famously devoted, and the lot scene and crowd at Alpine always brought a particular Midwestern exuberance to the proceedings.
From what we have catalogued here, the Dylan cover "Just Like Tom Thumb's Blues" is worth singling out. The Dead played this song periodically across several decades, and it fits Garcia's voice and sensibility so naturally that it can feel like a Dead original — weary, cinematic, a little bruised around the edges. When Garcia leaned into Dylan's imagery with that tone of his, something alchemical happened. And then there's the eternal gravity of Drums, that nightly ritual of percussion and open space that allowed Phil, Mickey, and Billy to do what few bands ever dared — stop the show entirely and turn it over to pure rhythm and exploration. Whatever followed Drums on this night would have emerged from that collective trance. Recording details for this show may vary — consult the taper notes if available, as Alpine sources range from clean soundboards to warm audience captures with the crowd mixed naturally into the room. Either way, cue up "Tom Thumb's Blues" and let Garcia do the rest.