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Bob Dylan’s Greatest Songs of the 1980s

20 songs worth hearing from Dylan’s most overlooked decade

Bob Dylan

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The 1980s are often seen as the absolute nadir of Bob Dylan‘s career. The man himself has even been very critical of the work he did during the Reagan decade. “I can still play those songs,” he told Rolling Stone in 2004. “But I probably can’t listen to those records. I’ll hear too many faults. I was just being swept along with the current when I was making those records. I don’t think my talent was under control.”

That’s arguably true of 1986’s Knocked Out Loaded and 1988’s Down In The Groove – but in fact, the rest of the Eighties were far from a wash for Dylan. He worked consistently through the decade and released a wide variety of material. Some of it’s pretty bad – avoid “Trust Yourself” and “Rank Strangers” at all costs – but there are tons of hidden gems from that period. Here are our picks for 20 classics from Dylan’s Eighties. Listen to the Spotify playlist as you read, and share your own favorite Dylan songs from this era in the comments section.

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‘Pressing On’ (1980)

Bob Dylan was firmly in his "Jesus Is Coming" period when the 1980s began.  Audiences that flocked to his concerts were stunned to learn they had to sit through an entire show of gospel songs, without a single oldie in the mix. They also got to see an absolutely killer band, and Dylan singing with incredible passion and force. The show often wrapped up with Dylan at the piano belting out this song. The gospel number has been covered by acts including John Doe of X and the Chicago Mass Choir, and it deserves to be sung at every church in America. Don't get too tripped up on the message. Give it a listen.

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‘Solid Rock’ (1980)

The release of Bob Dylan's 1979 born-again LP Slow Train Coming was a major event, and the album hit Number Three on the Billboard Hot 100. Less than a year later he released Saved, which was greeted like the second moon landing. It was a million times less interesting the second time around, and his label was even reluctant about putting it out. But the album has never really gotten a fair hearing. "Solid Rock" is one of the highlights, and it firmly explains Dylan's dedication to his new beliefs. "I won't let go, and I can't let go," he sings. "And I can't let go, won't get go and I can't let go no more." A few years later, he let go and re-embraced his Jewish heritage.

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‘The Groom’s Still Waiting At The Altar’ (1981)

Dylan's quality control hit an all-time low in the early Eighties. Over and over again, he'd record a great song, then cut it off the album in favor of far inferior work. The trend began in 1981 with "The Groom's Still Waiting At The Altar." He somehow felt that "Lenny Bruce" and "Dead Man, Dead Man" deserved a slot on Shot of Love more than this one. Four years later, he realized his error and – in an unprecedented move – added it to all subsequent releases of the album.

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‘Caribbean Wind’ (1981)

No matter how much promise a song shows, if Dylan gets frustrated with something he's written, he tends to chuck it overboard rather than try and fix it. That was the sad fate of "Caribbean Wind." The nearly six-minute epic could have elevated Shot of Love, but he couldn't seem to find the song and he gave up. It was salvaged four years later for his Biograph boxed set. That version certainly sounds done, and he even played it live once in November 1980.

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‘Every Grain of Sand’ demo (1981)

This is one of the final songs that Dylan wrote during his religious period, and one of his finest. Few people were paying attention to Dylan's new music by 1981, but those that did recognized this as one of the most touching and sublime works of his career – up there with anything he wrote in the 1960s. The stripped down demo from his Bootleg Series is even better. You can even hear Dylan's dogs barking in the background.

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‘Jokerman’ (1983)

Dylan recruited Dire Straits guitarist Mark Knopfler to produce his 1983 LP Infidels, a supposedly secular album – though this song includes references to Sodom and Gomorrah, Leviticus, Deuteronomy and the "rich man without any name" in the "fiery furnace." It's one trippy song, and it rocks harder than most anything else Dylan did in the 1980s. The definitive version was performed on Late Night With David Letterman with LA punk band the Plugz. Check it out on YouTube.

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‘I & I’ (1983)

Bob Dylan and reggae aren't two things commonly put together, but the legendary rhythm section of Sly Dunbar and Robbie Shakespeare added a light Jamaican touch to some of the material on Infidels. This pretty, mystical song is another one of those allegedly secular songs that still has lines like "Took a stranger to teach me to look into justice's beautiful face/And to see an eye for an eye and a tooth for a tooth."

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‘Sweetheart Like You’ (1983)

Only Dylan would compliment a woman with this line, playing on a Bible verse: "They say in your father's house there's many mansions/Each one of them got a fireproof floor." Then, in the same song, he says, "A woman like you should be at home/That's where you belong/Watching out for someone who loves you true/Who would never do you wrong." It's one of Dylan's most misogynistic lines, and this is a man who five years earlier compared a woman to a horse in "New Pony." Lyrics aside, though, this is a gorgeous, overlooked ballad.

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‘Someone’s Got A Hold On My Heart’ (1983)

Dylan recorded a ton of great songs for Infidels, and then proceeded to cut some of the best ones off the album. This one resurfaced two years later as "Tight Connection To My Heart," but it failed to capture the vibe of the original. It also removed most of the religious references in favor of recycled lines from movies like The Maltese Falcon and Serpico. (Dylan must have been watching a lot of movies in the mid-1980s – his albums from that time are littered with film quotations.) "Someone's Got A Hold On My Heart" reached perfection when Dylan played it at New York's Supper Club in November 1993. Those shows were filmed, though the footage is rarely seen; they really deserve a DVD release one of these days.

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‘Blind Willie McTell’ (1983)

One of Dylan's greatest songs almost never saw the light of day. "I don't think I recorded it right," he told Rolling Stone in 1984, a few months after discarding the tune during the Infidels sessions. But "Blind Willie McTell" was widely bootlegged, and fans loved it – so Dylan eventually gave in and released it with the first volumes of the Bootleg Series in 1991. He's played it fairly often in concert since then, using an arrangement that seems to draw on the Band's 1993 cover version.

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‘Tangled Up In Blue,’ ‘Real Live’ version (1984)

This may seem like cheating, but the version of "Tangled Up In Blue" that Dylan performed on his 1984 European tour was so radically different from the 1974 original that it should count as its own song. "On Real Live it's more like it should have been," Dylan told Cameron Crowe in 1985. "I was never really happy with it. I guess I was just trying to make it like a painting where you can see the different parts but then you also see the whole of it. With that particular song, that's what I was trying to do . . . with the concept of time, and the way the characters change from the first person to the third person, and you're never quite sure if the third person is talking or the first person is talking. But as you look at the whole thing it really doesn't matter. On Real Live, the imagery is better and more the way I would have liked it than on the original recording."

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‘Dark Eyes’ (1985)

In 1985, Dylan decided to made a modern-sounding record. Sadly, he couldn't have picked a single worse year to try that tactic. Records made in 1985 sound more dated now than the ones recorded at pretty much any other time in rock history. And the vision of Empire Burlesque studio collaborator Arthur Baker – best known for his work with dance acts like New Order, and a handful of Bruce Springsteen club remixes – didn't exactly line up with Dylan's. Baker did have one great idea, though: He suggested that Dylan end the album with one stripped down acoustic song. Dylan initially balked and claimed he didn't have such a song, but he got inspired after seeing a sad woman with "dark eyes" at at a New York hotel. He wrote this song that very night. Ten years later, he brought Patti Smith on tour with him and told her they could duet on any song in his catalog. She picked this one, and they closed out most of the shows with it. Look for it on YouTube.

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‘When The Night Comes Falling From The Sky’ (1985)

Sometimes a song doesn't really come alive until it starts to get played in concert. "When The Night Comes Falling From The Sky" is rather flat and forgettable on Empire Burlesque, but when Dylan played it live with Tom Petty & the Heartbreakers live in 1986 it was consistently stunning. Unfortunately, you'll have to comb through the bootlegs to hear that version. The best sounding unofficial recording comes from Sydney, Australia in 1986.

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‘Seeing the Real You At Last’ (1985)

This is another one that was butchered on Empire Burlesque. The drums sound terrible. The horns are even worse. Even the guitar sound is horrid. The only saving grace is Dylan's lyrics, which were largely cobbled together from old movies. In 2002, though, Dylan opened up a bunch of shows with "Seeing the Real You At Last," revealing the great song hidden underneath that brittle production. The new live arrangement was absolutely staggering. These shows weren't released, of course, because – aside from 1995's MTV Unplugged – Dylan has yet to release a single show from the Never Ending Tour. It's a real travesty, because it means gems like this remain forever buried.

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‘Brownsville Girl’ (1986)

1986's Knocked Out Loaded may well be the worst album in Dylan's vast catalog. (Well, maybe it's the second worst, after 1988's Down In The Groove.) Even the title suggested it was something he might have tossed together while not exactly in the best mental state. The songs are mainly covers or co-written with people like Tom Petty and Carole Bayer Sager. The only song worth listening to is "Brownsville Girl," an 11-minute epic Dylan wrote with playwright Sam Shepard. It's a bizarre masterpiece that almost redeems the whole album. The narrative is all over the place, but it keeps going back to a memory of standing in line for a Gregory Peck movie that sounds like 1950's The Gunfighter. The song was originally tiled "New Danville Girl" and intended for Empire Burlesque, but this is a rare example of a Dylan song that improved when revisited more than a year later.

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‘Silvio’ (1988)

There's nothing on Down In The Groove as good as "Brownsville Girl," but "Silvio" – co-written with Grateful Dead lyricist Robert Hunter – is the clear highlight. Dylan likes it so much, he played it live 595 times between 1988 and 2004. In 1998 alone, he performed it 99 times. To put that in perspective, he's played this song live more often than "Forever Young," "I Shall Be Released" or "Knockin' on Heaven's Door." It's not quite worthy of all that attention, but it's definitely worth a listen.

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‘Most Of The Time’ (1989)

By 1989, Dylan knew he had to start making albums where he actually cared. Taking Bono's advice, he agreed to work with producer Daniel Lanois. They cut Oh Mercy down in New Orleans, in sessions described at great length in Dylan's 2004 memoir Chronicles: Volume One. The result was a huge leap past all his other post-Infidels work, highlighted by the emotionally charged "Most Of The Time." Dylan has been critical of Lanois' heavy-handed production, and he released a stripped-down version of the song on 2008's Tell Tale Signs. Both versions are must-hears.

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‘Shooting Star’ (1989)

Dylan is very good at ending his albums on exactly the right note. He did it in 1965 with "Desolation Row," and again the following year with "Sad Eyed Lady Of The Lowlands." Blood on the Tracks wouldn't be the same without "Buckets of Rain" at the end, nor would the unfairly maligned Street Legal work without closing out with "Where Are You Tonight? (Journey Through Dark Heat)." Oh Mercy, meanwhile, concludes with "Shooting Star," which echoes some of the self-doubt and regret heard earlier on "Most of The Time." "Saw a shooting star tonight/Slip away/Tomorrow will be another day/Guess it's too late to say the things to you/That you needed me to say."

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Kevin Mazur/WireImage

‘Series of Dreams’ (1989)

Much like Infidels six years earlier, Oh Mercy would have been a stronger album had Dylan not cut one of the best songs off the album. The absence of "Series of Dreams" significantly weakens the entire work. "Lanois liked the song," Dylan wrote in Chronicles. "He liked the bridge better, wanted the whole song to be like that. I knew what he meant, but it just couldn't be done." You want to smack your head when you read things like that. Thankfully, the song was remixed and released just two years later on The Bootleg Series Volumes 1-3 and they even made a video for it.  Another version cut for Oh Mercy can be heard on Tell Tale Signs.

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‘Dignity’ piano demo (1989)

It seems like Dylan really doesn't like what Lanois did to his songs. Over the past few years, he's re-released many of the songs from Oh Mercy and Time Out Of Mind in stripped down versions that remove most of the producer's work. This was the case for "Dignity," a song originally intended for Oh Mercy. The song was cut from the track list, then released on Greatest Hits Volume 3. In 2008, he released the original piano demo from 1989 – and it's great.  This is a song that got worse each time it was fiddled with, so stick with the original.

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In This Article: Bob Dylan, Greatest Songs

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