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Top 10 Bob Dylan Songs of the Last 20 Years (1992-2011)

Bob Dylan
Kevin Winter, Getty Images

The last twenty years of Bob Dylan‘s recording career will, of course, never match up with his genre and era-defining masterpieces of the ’60s, but it’s hard to find a body of work among any of his peers that stacks up to the efforts and accomplishment of his fourth and fifth decades. To celebrate Dylan’s 70th birthday today, May 24, 2011, we present the Top 10 Bob Dylan Songs of the Last 20 Years.


Bob Dylan Good as I Been to You
10

'Frankie and Albert'

From 'Good as I Been to You' (1992)
 
 

Nobody, even Dylan himself, can muster up much of a defense for his listless, overproduced 1990 album 'Under the Red Sky.' So it makes sense that he started off his late-career renaissance by returning to his folk beginnings. On his 1992 album 'Good as I Been to You,' he sings traditional covers, such as this tale of betrayal and murder, with only the accompaniment of his own surprisingly dexterous acoustic guitar.

 
Bob Dylan Modern Times
9

'Spirit on the Water'

From 'Modern Times' (2006)
 
 

Bob Dylan indulges his playful, romantic side on this leisurely, old-fashioned love song. As unkempt jazz guitar chords and a soft, but cracking snare keep you and your loved one close on the dance floor for nearly eight minutes, the rock icon throws a little challenge at his critics: "You think I'm over the hill / Think I'm past my prime / Let me see what you got / We can have a whopping good time."

 
Bob Dylan Lone Pilgrim
8

'Lone Pilgrim'

From 'World Gone Wrong' (1993)
 
 

For his second consecutive album of solo acoustic cover songs, Dylan delivered a darker selection of material that cut much deeper. This stark ballad finds the narrator visiting the graveyard of a lone pilgrim, who reaches out from the beyond to assure the guest that his soul is at peace in the next world, and asks Dylan only that he share this news with his worried family.

 
Bob Dylan Time Out of Mind
7

'Make You Feel My Love'

From 'Time Out of Mind' (1997)
 
 

Dylan's first album of original material in seven years is a weary, textured masterpiece that should rightfully dominate any conversation about his last 20 years of work. The album's bookends, 'Love Sick' and the epic 'Highlands,' among others, deserve serious consideration for this list. But we'll go with the opinion of his peers, three of whom -- Billy Joel, Garth Brooks and Adele -- took their versions of 'Make You Feel My Love' to the top of various sales charts all over the world.

 
Bob Dylan Thunder on the Mountain
6

'Thunder on the Mountain'

From 'Modern Times' (2006)
 
 

Whoa! Bob Dylan knows who Alicia Keys is? That's about the only thing more surprising than how powerfully and effortlessly Dylan and his band -- who've spent much of the last 20 years on the road together -- roll through the opening track from 2006's critically acclaimed album 'Modern Times.' Just last year rockabilly pioneer Wanda Jackson covered this track, and turned Dylan disciple Jack White loose on lead guitar to spectacular effect.

 
Bob Dylan Greatest Hits, Volume 3
5

'Dignity'

From 'Greatest Hits, Volume 3' (1994)
 
 

According to his 2004 autobiography, Dylan and producer Daniel Lanois first tried to record this song for 1989's 'Oh Mercy' album, but a series of recording experiments and guest musicians left them frustrated with numerous unfinished versions of the track. Thankfully, a clearly re-invigorated Dylan recorded a bright, upbeat version of this lyrical rumination on self-respect for 1994's 'Greatest Hits, Volume 3.'

 
Bob Dylan Beyond Here Lies Nothin
4

'Beyond Here Lies Nothin''

From 'Together Through Life' (2009)
 
 

The most recent of Bob Dylan's non-holiday studio albums finds him capping our (arbitrary) survey of his last 20 years by once again shaking things up, recruiting Mike Campbell from the Heartbreakers and David Hidalgo from Los Lobos for a loose collection of swampy, horn and accordion-filled songs like this one. To our ears, much of the message is about how love simultaneously messes up and justifies pretty much every moment of your life.

 
Bob Dylan Not Dark Yet
3

'Not Dark Yet'

From 'Time Out of Mind' (1997)
 
 

The second single from 'Time Out of Mind' is a stately, surprisingly clear-sung accounting of a painful life from a man who sees the end closing in on him. As you can imagine, it's also depressing as hell; the poor guy can't connect with the joy of living anymore:"She wrote me a letter and she wrote it so kind / She put down in writing what was in her mind / I just don’t see why I should even care / It’s not dark yet, but it’s getting there."

 
Bob Dylan Things Have Changed
2

'Things Have Changed'

From the 'Wonder Boys' Soundtrack (2000)
 
 

Dylan's contribution to the excellent 2000 film 'Wonder Boys' occupies a nearly perfect middle ground between 1997's pessimistic 'Time Out of Mind' and the then yet-to-be released, more hopeful 2001 album 'Love and Theft.' While he insists survival is his only goal now -- "I'm locked in tight / I'm out of range / I used to care / But things have changed" -- the driving beat and his upbeat, seemingly bemused vocal delivery seems to indicate otherwise.

 
Bob Dylan Love and Theft
1

'Mississippi'

From 'Love and Theft' (2001)
 
 

After the impressive but intentionally downbeat and resigned 'Time Out of Mind,' Bob Dylan solidified his creative comeback with the much livelier 'Love and Theft.' As on 'Not Dark Yet,' he's thinking of the journey's end, but this time, "My heart is not weary / It's alive, it's free / I've got nothing but affection for all those who've sailed with me." He also makes it clear he's got no plans to sit still just yet: "Stick with me baby / Stick with me anyhow / Things should start to get interesting right about now."

 

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