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. 

More than a few people walked out of High Fidelity in 2000 with the same question: "What was that amazing Bob Dylan song they played near the end?" The answer was "Most of the Time," a haunting tune of regret from Oh Mercy. Much like "Everything Is Broken," they are the words of a man that's made more than a few mistakes, though this one is dipped in heartbreak. "Most of the time," he sings. "She ain’t even in my mind/I wouldn’t know her if I saw her/She’s that far behind." There are two amazing alternate versions on Tell Tale Signs that take out some of the Lanois production. 

Dylan's 1981 LP Shot of Love is an extremely mixed effort, but it wraps up with the absolutely sublime "Every Grain of Sand." Despite songs like "Property of Jesus," Shot of Love isn't a strictly Christian album, but it's easy to spot the Biblical references on "Every Grain of Sand." "Like Cain, I now behold this chain of events that I must break," Dylan sings. "In the fury of the moment I can see the Master’s hand/In every leaf that trembles, in every grain of sand." Many fans feel the definitive version is the home demo on the first Bootleg Series. You can hear Dylan's dogs barking in the background, but somehow it only adds to the song. 

In some alternate universe, Bob Dylan included "Blind Willie McTell," "Foot of Pride" and "Someone's Got a Hold on My Heart" on 1983's Infidels and then launched a triumphant tour with the New Wave band Plugz, who backed him on Letterman in 1984. It would have given him a huge comeback and put him on an entirely different trajectory in the 1980s, but it wasn't to be. "Blind Willie McTell" is one of the best songs he wrote in any decade, but he simply didn't think it was worthy of release at the time.

"I didn't think I recorded it right," he told Rolling Stone in 1984. "But I don't know why that stuff gets out on me. I mean, it never seems to get out on other people." Dylan finally put it out himself on the Bootleg Series in 1991, and it was hailed as a jaw-dropping masterpiece. After the Band recorded it in 1993, Dylan added it into his live show and it stayed in rotation over the next two decades. 

In the early 1980s, Dylan spent a lot of time sailing around the Caribbean. "Me and another guy have a boat down there," he told Rolling Stone in 1984. "'Jokerman' kinda came to me in the islands. It's very mystical. The shapes there, and shadows, seem to be so ancient. The song was sorta inspired by these spirits they call jumbis." The mysterious song kicks off Infidels, and Dylan released it as a single that failed to even chart. Still, he promoted it with a video and then performed it on his legendary Letterman appearance in 1984. The song then disappeared for another 10 years, when out of nowhere he played it at 103 consecutive shows.