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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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Ebet Roberts/Redferns

‘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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Ebet Roberts/Redferns

‘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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Kevin Mazur/WireImage

‘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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