Bob Dylan broke free from his rigid setlist at the end of show in Broomfield, Colorado earlier this week to honor the late Tom Petty with a moving rendition of his 1991 hit “Learning to Fly.” It was the first time he’d honored an artist by covering of his tunes right after he passed away since he played “Rumble” in honor of Link Wray back in 2005, but it wasn’t a huge surprise. Petty and Dylan became close when they toured together in 1986 and got grew even tighter a few years later when they formed the Traveling Wilburys. “It’s shocking, crushing news,” Dylan told Rolling Stone right after Petty passed away. “I thought the world of Tom. He was a great performer, full of the light, a friend, and I’ll never forget him.”
Dylan was a low point in his career when he hit the road with Petty in 1986. “I had no connection to any kind of inspiration,” he wrote in his 2004 memoir Chronicles. “Whatever was there had all vanished and shrunk. Tom was at the top of his game and I was at the bottom of mine. Everything was smashed. I didn’t have the skill to touch their raw nerves, couldn’t penetrate the surfaces.”
Video from the tour doesn’t quite show Dylan as completely “vanished and shrunk.” Most shows were actually pretty amazing even if the albums he cut around this time are among the worst of his whole career. Here’s a killer performance of “When the Night Comes Falling From the Sky” at a Sydney, Australia show in 1986. It’s a song with a rather torturous history. It was originally cut in 1985 at the Power Station in New York with Steve Van Zandt, Max Weinberg and Roy Bittan from the E Street Band. “Dylan said to me, ‘I don’t know, it sounds like Bruce Springsteen,'” producer Arthur Baker told Rolling Stone in 2015. “And I said, ‘What did you expect? You’ve got Springsteen’s band.'” The E Street Band version would eventually surface on the first volume of Dylan’s Bootleg Series in 1991, but for Empire Burlesque it was recorded again with Sly Dunbar, Robbie Shakespeare, Al Kooper, Stu Kimball and Bashiri Johnson.
The song didn’t truly live up to its potential until Petty and the Heartbreakers got their hands on it for the tour. It’s very rare that the Heartbreakers and the E Street Band had the chance play the same tune, and in this case the Heartbreakers clearly got the best out of it. It makes both renditions cut for Empire Burlesque seem lifeless by comparison. By coincidence or not, Dylan hasn’t even attempted to play the song live since the end of the Heartbreakers tour in 1987.
The Heartbreakers are undoubtably one of the greatest backing bands Dylan has ever worked with, capable of playing any song in his catalog with one second’s notice. It would be incredible if he took them out on the road for a future tour now that they are a band without a leader, but Dylan is very happy with the current iteration of his Never Ending Tour band and such a drastic change is almost impossible to imagine. At the very least, they should chronicle their 1986/87 tour on a future chapter of the Bootleg Series.