There are concerts that are good. There are concerts that are great. And then there are concerts where two separate gravitational fields collide on Halloween night in a university arena on the Near West Side of Chicago, and the crowd is in costume, and a deadpan comedian performs between sets, and the police are wading into the floor arresting people, and somehow none of that is the most remarkable thing about the evening.
The most remarkable thing is that both of these men are here at all.
Phil Lesh should not have been standing on a stage in October 1999. Ten months earlier he had been at the Mayo Clinic in Jacksonville, Florida, receiving a new liver.
Lesh had discovered in 1992 that he had been infected by Hepatitis C. In September 1998 he underwent a spell of internal bleeding that made clear the seriousness of the damage to his liver. The surgery lasted roughly four hours. The liver he received belonged to a young man named Cody, who had died in some sort of automobile or bicycle accident. Lesh knew little else about him — only his name — but said he prayed for him every night.
He was at death's door. But he made a marvelous recovery, which he ascribed to the outpouring of spiritual support and well-wishes from Deadheads around the world. "I could feel it," he said, "and it brought me back really quickly. I owe them everything, including my life."
Four months after surgery, he was back on a stage. And at every show from that point forward, somewhere in the evening, the music would pause and Phil Lesh would speak directly to the audience. "Save the life of someone you'll never meet," he would tell them, urging everyone in the room to register as an organ donor. At some festivals, he signed fans' donor cards himself.
The fall 1999 tour with Bob Dylan was the biggest excursion Lesh had undertaken since the transplant gave him a new lease on life. He was 59 years old, playing on borrowed time, in the most literal sense possible. The shows weren't a comeback. They were a gift.
The connection between Bob Dylan and the Grateful Dead ran deep and strange, going back decades.
Dylan had toured with the Dead in the summer of 1987 — six shows, coast to coast — and the experience had done something to him. He rediscovered his songs through his association with the Dead, and they resurrected a new soul in Dylan. The alternating setlists, the spontaneous reinvention of old material, the willingness to let a song breathe and change every night — Dylan took all of that with him when the tour ended. He began covering "Friend of the Devil" regularly, making it a fixture of his setlists throughout the mid-1990s. The two worlds had always shared an audience — people who collected bootlegs, who followed tours, who understood that the live show was the real thing and the studio record was just the sketch.
When the fall 1999 co-bill was announced, rock fans were overjoyed. Dylan and the Dead had crossed paths many times over the years, sharing both a common musical vision and an audience of many of the same devoted fans.
The tour opened October 26. By the time it reached Chicago on Halloween night — show six of twenty — it had already absorbed significant turbulence. Steve Kimock, the cornerstone of Phil Lesh and Friends, had walked off the tour after the very first show in Champaign, Illinois, without ever giving a full accounting of why. Complicating matters further was the dismissal of roadies Steve Parish and Ramrod — veterans of both the Dead and Dylan's road crews — apparently over old politics between the two camps. Lesh addressed this on his website under his pen name Reddy Kilowatt: "I will not allow old politics and ego to poison what I am striving to do — a tour where the only mission is to do our best to honor the music, the musicians, and the community."
What Kimock's departure actually did was open a door. Phil Lesh and Friends played the next two dates with Paul Barrere and Billy Payne of Little Feat before guitarist Derek Trucks signed on to the tour in time for the Halloween show in Chicago — which turned out to be the last show with the Little Feat players. Trucks was 20 years old. He had been playing with the Allman Brothers Band since he was twelve. On Halloween night 1999 at the UIC Pavilion, he walked onto a stage alongside Phil Lesh, Paul Barrere, Billy Payne, and drummer John Molo, and played some of the most complex improvisational music in the American canon.
The UIC Pavilion opened in 1982 at 525 South Racine Avenue, on the campus of the University of Illinois Chicago, designed by the architecture firm Skidmore, Owings and Merrill. It opened with a Loverboy concert. By 1999 it had accumulated its own history — Prince had played his final show of the 1999 Tour there in April 1983; the Grateful Dead had played three nights there in April 1987, the same year Dylan had toured with them. The room had a particular kind of magic that resisted easy explanation. At first glance there was nothing special about the place — a typical 10,000-seat sports arena. Yet many bands had given some of their finest Chicago-area performances there. Something about the room, the sightlines, the proximity of the crowd to the stage, produced nights that the people who were there never forgot.
Halloween sent an extra current through it. The floor was general admission, and the crowd had arrived in costume — skeletons, wizards, tie-dye phantoms, the full Deadhead taxonomy rendered in orange and black. It was a strange, electric atmosphere even before a note was played.
Phil Lesh and Friends opened with a raging version of "St. Stephen" which broke down into an unexpected and musically challenging passage — more Schoenberg than the Shangri-Las — before crystallizing into stride piano and then the calypso complexity of "Blue Sky Jam." The set wove in and out of Dead material and long-form improvisation, Trucks and Barrere trading leads while Lesh anchored everything from below, his six-string bass filling the room with the low-end authority that had defined thirty years of Grateful Dead concerts. John Molo on drums kept the whole structure from floating away entirely.
Inside the crowded arena, however, something else was happening. Police waded into the floor to bust concertgoers for smoking illegal substances — a crackdown that hadn't been seen in a docile concert setting since the early '70s. Officers in some cases brought their handcuffed suspects out through the backstage and dressing room areas, past the musicians themselves. The crowd on the floor watched it with a mixture of disbelief and the particular stoicism of people who have attended a lot of Grateful Dead shows and have seen worse.
Between the two sets, the evening took its strangest turn. Comedian Steven Wright performed — his unique deadpan perspective turning common concepts into hilarious one-line observations, warming the crowd for Dylan. A room full of costumed Deadheads watching Steven Wright in a university arena in Chicago on Halloween night, waiting for Bob Dylan to take the stage. There are nights that exist outside of any normal category.
Then Dylan came out.
He opened the acoustic set with "I Am the Man Thomas" — a Ralph Stanley bluegrass song — and rambled through classic selections including "It's Alright Ma" and "Love Minus Zero" before "Tangled Up in Blue" drew the acoustic portion to a rousing conclusion. Once the band plugged in they were truly formidable. The triple guitar attack of Dylan, Larry Campbell, and Charlie Sexton turned "All Along the Watchtower" into a raging inferno worthy of Hendrix or Neil Young, and they shredded "Highway 61 Revisited" with the muscular grit of a Chicago blues band. Just as easily, the group turned "Simple Twist of Fate" and "Not Dark Yet" into emotionally haunting snapshots of life.
Then, late in the set, Phil Lesh walked back out. The man with the borrowed liver, standing beside the man who had rediscovered himself through the Dead, playing songs that belonged to both of their worlds simultaneously. The show was described by those who were there as stirring and brilliant — a Halloween night for the ages in the smoke-filled UIC Pavilion.
The tour ran for twenty dates, ending in November. The UIC Pavilion was later renamed Credit Union 1 Arena in 2018, after a fifteen-year naming rights deal. It still hosts basketball games and occasional concerts, the same brutalist concrete shell that held that Halloween crowd in costumes, the police crackdown, Steven Wright, Derek Trucks at 20, Phil Lesh with Cody's liver, Bob Dylan playing bluegrass.
The 1987 Dylan-Dead tour, the transplant, the Kimock walkout, the roadie politics, the Halloween crowd — all of it converging on one night in a university arena in Chicago, two worlds colliding in the dark.
The stage remembers.