Readers’ Poll: The 10 Best Bob Dylan Songs of the 1980s

Time and time again throughout the 1980s, Bob Dylan would record an absolutely brilliant song and then make the baffling decision to leave it off his album. "Series of Dreams" is a wonderful example of this frustrating tendency. The gorgeously trippy tune was cut for 1989's Oh Mercy, but Dylan wasn't happy with it and the more producer Daniel Lanois pushed the harder Dylan resisted, flatly stating it was too long and he didn't want to cut any of it. Just two years later, it was resurrected when a remixed version wrapped up The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991. They made a video for it and by 1993 Dylan was even playing it live. An alternate take surfaced in 2008 on The Bootleg Series Vol. 8: Tell Tale Signs: Rare and Unreleased 1989–2006.

With the exception of his work with Jacques Levy on Desire and a couple of songs he composed with members of the Band, Bob Dylan wrote almost all of his pre-1980s material without outside help. But as soon as the Eighties hit, he began co-writing songs with everyone from Tom Petty to Carole Bayer Sager, Tim Drummond, Robert Hunter and even Bono. His mightiest collaboration was the 11-minute epic "Brownsville Girl" (co-written with Sam Shepard) on 1986's otherwise abysmal Knocked Out Loaded. It bounces all over the place, but keeps returning to his dim memory of seeing watching the 1950 Gregory Peck movie The Gunfighter. Nobody knows who wrote lines like "people don’t do what they believe in, they just do what’s most convenient and then repent" and "even the swap meets around here are getting corrupt," but they're amazing. 

In early 1985, Bob Dylan was just about done recording Empire Burlesque when producer Arthur Baker asked him to write a simple acoustic song to wrap up the otherwise slick, modern-sounding album. Dylan didn't have the material until he stumbled across a prostitute in the lobby of New York's Plaza Hotel late one night. "She had blue circles around her eyes, black eyeliner, dark eyes," he wrote in 2004's Chronicles. "She looked like she had been beaten up and was afraid that she'd get beaten up again." The sad image inspired Dylan to write "Dark Eyes" in his Plaza hotel room as he looked down at Central Park. It was another ten years before he first played it live, which came at the request of Patti Smith when he told her to pick any song from his catalog for them to sing as a duet. 

By 1989 it seemed quite possible that Dylan would never make another great album. Despite a fun series of tours with Tom Petty and the Grateful Dead, his last three albums were extreme disappointments. Even worse, sometimes it seemed like he was barely even trying. "I had no connection to any kind of inspiration," he wrote in Chronicles. "Whatever was there to begin with had all vanished and shrunk." Things turned around when Bono suggested he work with Daniel Lanois, and he headed down to New Orleans to work with the producer on Oh Mercy. One of the new songs he wrote, "Everything Is Broken," was a clear reflection of his state of mind at the time, especially after he severely injured his hand and was unable to play guitar for a long period of time. Somewhat ironically, a song about his broken state was one of the first signs that he actually wasn't broken and still quite capable of greatness. 

At first glance, the Traveling Wilburys song "Tweeter and the Monkey Man" (written by Tom Petty and Bob Dylan) seems like a dig at Bruce Springsteen. After all, the song is littered with references to Springsteen songs like "Thunder Road," "Stolen Car," "Mansion on the Hill," "State Trooper" and even "Lion's Den." But in a 2013 interview with Rolling Stone, Petty swore it was a loving tribute.

"It was not meant to mock [Springsteen] at all," said Petty. "It started with Bob Dylan saying, 'I want to write a song about a guy named Tweeter. And it needs somebody else.' I said, 'The Monkey Man.' And he says, 'Perfect, 'Tweeter and the Monkey Man.'' And he said, 'Okay, I want to write the story and I want to set it in New Jersey.' I was like, 'OK, New Jersey.' And he was like, 'Yeah, we could use references to Bruce Springsteen titles.' He clearly meant it as praise."

"Sweetheart Like You" is a the sort of love song only Bob Dylan could write. "You know, a woman like you should be at home," he sings on the 1983 tune.  "That’s where you belong/Watching out for someone who loves you true." That particular bit rubbed a few people the wrong way. "That line didn't come out exactly the way I wanted it to," he told Rolling Stone in 1984.  "But, uh . . . I could easily have changed that line to make it not so overly, uh, tender, you know? But I think the concept still woulda been the same. You see a fine-lookin' woman walking down the street, you start goin', 'Well, what are you doin' on the street? You're so fine, what do you need all this for?'"

That one line aside, it's a rather beautiful song that he promoted with one of his first videos. It features Dylan and his band playing to an empty bar while a rather sad janitor looks on. He has yet to play the song live.