Best Bob Dylan Songs Of The 1990’s

The 1980s were a turbulent decade for Bob Dylan. He converted to born again Christianity, released a slew of critically divisive records, and ended the decade on a particularly high note: ‘Oh Mercy.’ While not as prolific as the previous decade, the 1990s were no less confounding for the folk rock icon’s fans. Dylan explored traditional folk music, children’s songs, and some of his darkest, most emotional musings ever. Here are ten of the finest endeavors of one of Dylan’s most misunderstood eras. (Note that covers have been included in this collection, which is apt, considering Dylan focused himself so heavily on them during the 1990s. To create a list like this without them would dismiss a sizable chunk of his work during this time.)

# – 10. ‘Unbelievable’ – ‘Under The Red Sky’ – 1990

Bob Dylan’s first foray into the 1990s is often viewed even harsher than his most lamented efforts of the 80s. Under The Red Sky is an album plagued by several tracks so awful that their tainted aura transcends their individual spheres to corrupt the whole entity. (We’re all looking at you, ‘Wiggle Wiggle.’) When broken down into specific songs, however, Under The Red Sky actually houses some surprisingly good tracks that hold up very well. ‘Unbelievable’ is one of them, a fantastic romp through characteristically screechy harmonicas, bluesy rock and roll, and fantastic lyrics.

One could make a parallel with this record to 1970’s ‘Self Portrait.’ Were all of the tracks worth writing home about? Certainly not. Were the gems worth holding onto due to Dylan’s infectious enthusiasm? Absolutely. “All the silver, all the gold, all the sweethearts you can hold, that don’t come back with stories untold are hanging on a tree. It’s unbelievable, like a lead balloon. It’s so impossible to even learn the tune…”

# 9 – ‘If You Belonged To Me’ – ‘Traveling Wilburys Vol. 3’ – 1990

Despite the devastating loss of Roy Orbison, the Traveling Wilburys powered through into the 1990s to release their second and final album, ‘Vol. 3.’ (The ‘second volume,’ according to George Harrison, was essentially dominated by the bootleg community.) Comprised of the remaining Wilburys: Dylan, Harrison, Tom Petty, and Jeff Lynne, ‘Vol. 3’ was very similar to its predecessor – which is why it’s so splendidly good.

The Traveling Wilburys was a compelling supergroup because it was clearly a labor of love and fun. The songs didn’t take themselves seriously, the productions were joyous escapades through lovely melodies and quirky lyrics, and the chemistry between the stars was undeniable. They never properly disclosed who wrote what, but Bob Dylan’s lyrical style is riddled throughout a good majority of the songs. One of those is ‘If You Belonged To Me,’ a song he also sang. It embodies everything that was so special about the Wilburys: community, love of music, and friendship.

# 8 –  ‘Step It up and Go’ – ‘Good As I Been To You’ – 1992

In 1992, Bob Dylan did something unexpected: he reverted back to his roots. ‘Good As I Been To You’ was the first of two albums that explored some of his favorite traditional folk standards in new, unique styles. While the idea has been floated that he recorded them to finish out a contract, the two albums offer some extraordinary performances nonetheless. Bob Dylan could still play one mean acoustic guitar, and these minimalistic demo-like albums are gems.

Dylan wanted to record songs that got lost in translation and hadn’t been touched for many years. Though the second journey through this would prove more fruitful, ‘Good As I Been To You’ was Dylan’s first solo album in the 90s to be received well. ‘Step It up and Go’ is a fast-paced blues standard based on the 1939 song ‘Bottle It up and Go,’ originally recorded by the delta blues artist Tommy McClennan. It’s arguably one of the best tracks on the effort, chock-full of personality and groove.

There are no version of Bob Dylan doing Step It Up and Go on YouTube, so we used Classicrockhistory.com editor-in-chief Brian Kachejian’s version.

 # – 7  ‘God Knows’ – ‘Under The Red Sky’ – 1990

‘God Knows’ is another excellent song on Under The Red Sky that also gets drowned out by far inferior tracks. Throughout the decade, Dylan would perfect the song live, but its original release does hold a power unlike anything else in the world: that of the Vaughan brothers. Yes, both Jimmie Vaughan and Stevie Ray Vaughan are highlighted on ‘God Knows.’ They compliment Dylan surprisingly well, infusing their licks into Dylan’s style without overpowering him.

For bootleg enthusiasts, which many Dylan fans are, the pinnacle version of the song may be the one he performed on his 1995 tour. There are several versions of it floating about, but the overall key change highlights the beauty of the song in a much more pleasing way.

# – 6 ‘Love Sick’ – ‘Time Out Of Mind’ – 1997

Any ‘best of’ or ‘highlights’ list of Bob Dylan’s 1990s catalog must, of course, reside heavily within Time Out Of Mind. The album was Dylan’s final release of the decade, and at the time some thought it may be his swansong. (2001’s’ ‘Love And Theft’ defied that.) The record scored Dylan a series of Grammy awards, including ‘Album of the Year.’ (Which he beat out Paul McCartney and Radiohead for.) It was also an ultimate return to form, concreting Dylan’s relevance as an aged artist transcended into a new era.

Time Out Of Mind has a very distinct sound, largely due to the production of Daniel Lanois, who also helmed ‘Oh Mercy’ in 1989. It was Dylan’s darkest record to date, brooding in atmospheric reverb, soft-spoken electric guitars, and intensely depressing imagery. Inspired by the failure of his second marriage, Time Out Of Mindis the ultimate breakup record. (Taking notes, Taylor Swift?) Millennials likely know it by Adele’s famous cover of ‘Make You Feel My Love.’

The opening to the album, which is also the tune Dylan performed at the Grammy awards, is ‘Love Sick.’ It’s an overture that sets a dramatic tone for the rest of the album. Is it blues? Is it folk rock? Perhaps, perhaps not. It’s just ‘Time Out Of Mind.’

# 5 –  ‘Delia’ – ‘World Gone Wrong’ – 1993

Shortly after the release of ‘Good As I Been To You,’ Dylan followed the album with ‘World Gone Wrong,’ a far sharper effort that truly honed in on his vision for a rootsy folk record. The song selection for the album is far more compelling, too, turning toward songs that Dylan could revitalize in authentic ways. It was lauded more than its predecessor, and snagged Dylan a Grammy, too.

Delia’ is such a treat, one hidden in the middle of ‘World Gone Wrong.’ It’s a folk standard that’s been built and rebuilt more times than one could count since 1900. Blind Willie McTell’s arrangement of the song is the version Dylan based his own off of. The stripped down arrangement highlights Dylan’s ability to compose within a box. McTell left behind a structure for artists like Dylan, but his personal triumph lies in his own acoustic composition around that frame.

# 4 – ‘Born In Time’ – ‘Under The Red Sky’ – 1990

‘Born In Time’ may be one of Bob Dylan’s most underappreciated songs. The song truly harnesses some of his most beautiful lyricism. It’s a love song about path not crossed and opportunities never taken. The arrangement on Under The Red Sky is an elegant one, based primarily around a strong piano influence. David Crosby softly croons behind Dylan on the choruses, too, going along with the star-studded theme of ‘Under The Red Sky.’

The song was realized earlier than 1990, however, since Dylan recorded a version in the key of E for ‘Oh Mercy.’ It may be the more superior rendition, in sooth, which is why Eric Clapton adapted it later in the decade. Either way, it’s a surreal, transcendent track and one of Dylan’s most poignant.

 

# 3 – ‘You Belong To Me’ – ‘Natural Born Killers’ Soundtrack – 1994

‘You Belong To Me’ was originally recorded for ‘Good As I Been To You,’ but was left off because it had already been touched on in popular culture. It’s a shame it wasn’t added, because Dylan’s rendition of the 1952 classic is absolutely jaw-dropping. (The song was originally written by Pee Wee King, Redd Stewart, and Chilton Price.)

In the vein of the two acoustic standard albums, the strongest element of ‘You Belong To Me’ is the way Dylan chose to arrange it. He brought it into the key of E, but chose to perform it on the fourth fret of the guitar in C form. This allows his instrumentation to explore the arrangement in a slightly more melodic way, especially in regard to his breathtaking hammer-on notes and slides.

Despite not being included on ‘Good As I Been To You,’ it was unearthed two years later for ‘Natural Born Killers,’ an Oliver Stone film penned by Quentin Tarantino. Such a gorgeous song may seem odd when set to a film about a mass killing spree, but it really does work. The end of the song includes a few lines from Woody Harrelson and Juliette Lewis, the film’s stars. They seal the deal, making it one of the most endearing songs Bob Dylan ever recorded.

# 2 – ‘Standing In The Doorway’ – ‘Time Out Of Mind’

Dylan’s lyricism has always been unmatched, unparalleled, and incomparable. Many of his spirited pursuits are abstract, though. Can one relate on a deeply personal level to ‘It’s Alright, Ma (I’m Only Bleeding)’? Perhaps not, because that was an era of Dylan’s philosophical ideas manifesting themselves in surreal poetry. Time Out Of Mind is equally well written, but instead is incredibly forthright. It’s an album you can relate to.

That’s likely the lasting impact of the record. It’s a painful, sorrowful, and heartbreaking collection of songs. All of those things, however, happen to each and every one of us in life. The tortured finale of a relationship may sound a lot like ‘Standing In The Doorway.’ The song is one of the longest on the album, utilizing its space to document the emptiness of life after the end.

# 1 – ‘Not Dark Yet’ – ‘Time Out Of Mind’ – 1997

‘Not Dark Yet’ was the first single released of Time Out Of Mind in 1997. It’s no less saddening than songs like ‘Standing In The Doorway’ or ‘Love Sick,’ wallowing in deep misery over its titular contemplation: “it’s not dark yet, but it’s getting there.” Dylan conveys a sense of apathy toward his lost relationship as if he’s trying to play it off like he doesn’t care what happened. He does, though, and it shows. Thus, it’s a very human song, and something everyone in the world will move through once, if not many times during their lifetime.

‘Not Dark Yet’ also brings one of the most magnificent instrumentations of ‘Time Out Of Mind’ to the table, accentuated strongly by a very eerie landscape. Dylan later expressed some dissatisfaction toward Lanois’ production in this regard, but that’s worth taking with a grain of salt. Fans and critics have agreed for nineteen years: that he did the content justice.

” Note: Fans of the song owe it to themselves to check out Robyn Hitchcock’s rendition from the 2005 ‘Talking Bob Dylan Blues’ concert, too. It’s one of the best covers of any of Dylan’s songs by any artist, accompanied beautifully by John Paul Jones.

Photo by Henryk Kotowski (svWiki) [GFDL (http://www.gnu.org/copyleft/fdl.html) or CC-BY-SA-3.0 (http://creativecommons.org/licenses/by-sa/3.0/)], via Wikimedia Commons

Updated Nov 2, 2023

Best Bob Dylan Songs Of The 1990’s article published on Classic RockHistory.com© 2023

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