Best Bob Dylan Songs of the 2000’s

Bob Dylan Songs 2000s

Photo: By Paparazzo Presents (Own work) [CC BY-SA 3.0 ( or GFDL (], via Wikimedia Commons

After Bob Dylan’s triumphant return to original music with the award winning ‘Time Out Of Mind’ in 1997, many thought the legend would hang up his harmonica rack for good. Instead, he opted to forge his path forward as resolutely as ever, resulting in a series of exceptional records. These albums aren’t just good for a Dylan entering old age – they muster enough punch and power to rival his efforts forty years prior.

The importance of that cannot be understated. Bob Dylan’s music continues to evolve year after year. With each evolution, Dylan reworks himself into an even more complex artist. This list is ten of his finest endeavors since 2000.

(Note that it does exclude ‘Christmas in the Heart’ and ‘Shadows in the Night.’ Both of those are lovely albums, but they’re ‘fun’ albums Dylan recorded to toy with carols and standards. They are splendid for what they are, but don’t belong in his top ten songs of this century.)

# 10 – ‘Jolene’ – ‘Together Through Life’ – 2009

Together Through Life’ is the spiritual end to a thematic trilogy of sorts, one including ‘Love And Theft’ and ‘Modern Times.’ During this era, Dylan explored a lot of traditional blues stylings, infusing them with a sharp, almost consistently electric four-piece outfit that has become his modern staple.

‘Jolene’ is a song that boasts a lively Dylan, a fantastic band, an infectiously fun central guitar riff, and a chorus that can get the dance floor moving. In the 2000s, Dylan toyed with snagging lyrical themes and structures from very old blues and folk music. He’d then move things around, infuse his own signature flair, and make something brand new. ‘Jolene’ has that vintage aura to it – which is wonderful. It’s also worth noting that many of the ‘Together Through Life’ tracks, including this one, were aided by Robert Hunter, a Grateful Dead lyricist.

“Well it’s a long old highway, don’t ever end. I’ve got a Saturday night special, I’m back again. I’ll sleep by your door, lay my life on the line. You probably don’t know, but I’m gonna’ make you mine. Jolene, Jolene – Baby, I am the king and you’re the queen.”


# 9 –   ‘Beyond Here Lies Nothin’ – ‘Together Through Life’ – 2009

‘Beyond Here Lies Nothin’ is the opening track to ‘Together Through Life.’ It’s a real scorcher, marking the album’s introduction with its most fierce song. It painfully details the aftermath of a treacherous relationship. The instrumentation is some of Dylan’s most unique, calling upon distorted blues guitar, accordions, and thick, thunderous percussion. Above all, the song may have been a resolute reminder of one simple, undeniable fact: it was 2009, and Dylan was still really, really cool.

During this era, Dylan continued to tour with his band playing his new songs and his old classics – as he continues to do now seven years later. Dylan has reworked all of his classics to embody these stylistic endeavors – songs like ‘Tangled Up In Blue’ sound perfectly in line with tunes like this. Anyone who has ever been to a Dylan concert knows that he reworks his own creations continually. This may be the most admirable part of Bob Dylan’s music the older he has gotten – he doesn’t rely on cashing in a paycheck for your nostalgia. He’s going to play music the way he wants to play it, and tailor it to his age.

‘Beyond Here Lies Nothin’ also really kicked off a line of uncharacteristically aggressive music videos for Bob Dylan. The NSFW video is centered around graphic domestic violence. This would later be echoed by the equally insane video for ‘Duquesne Whistle’ in 2012 and murderous music video last year for ‘The Night We Called It A Day.’

“I’m moving after midnight, down boulevards of broken cars. Don’t know what I’d do without it, without this love that we call ours. Beyond here lies nothin,’ nothin’ but the moon and stars.”

# 8 – ‘Cross The Green Mountain’ – ‘Gods and Generals Movie Soundtrack’ – 2003

2003’s ‘Gods and Generals’ was not a well received movie. It was too long, void of any real impactful purpose, and it aligned a bit too uncomfortably close to Confederate ideals for many. (It’s actually impressive it holds a 8% rating on Rotten Tomatoes. You can’t plan that kind of bad. It just happens.) The film’s only saving grace was Bob Dylan’s original song he penned for it – ‘Cross The Green Mountain.’

‘Cross The Green Mountain’ takes a lengthy queue from its host. It’s full mix is just over eight minutes. Unlike ‘Gods and Generals,’ though, it’s actually worth sitting through. It’s a remarkable song and a stunning excursion through Dylan’s storytelling. It was later released on 2008’s ‘Tell Tale Signs’ as well, which was the eighth volume of the Bootleg Series.

“Stars fell over Alabama, I saw each star. You’re walking in dreams, whoever you are. Chilled are the skies, keen is the frost. The ground’s froze hard, and the morning is lost.”

(Note that there are multiple edits of this song. The official music video cut it down to 3:14, which effectively butchered the storytelling.)

# 7 – ‘Tempest’ – ‘Tempest’ – 2012

Speaking of Bob Dylan’s lengthy storytelling, one would be remiss to not include the title track of ‘Tempest’ as one of his best in this century. Clocking in at nearly fourteen minutes of verses – no choruses or repeated imagery, it’s a doozy. If you’re inclined to print ‘Tempest’ out to follow along with the song, be sure your printer has at least six pages in the tray… because that’s how many you’ll need to print the whole thing.

Obviously, the song is incredibly divisive. Some hail it as one of Dylan’s best; others pin it as painful “slog” through an endless chasm of monotony. Yes, it’s hard to sit and listen to. That’s the point. The poet laureate of rock and roll challenges his listener to join him on a journey through the Titanic’s final moments. Dylan cascades through forty harsh, sorrowful verses and wants you to sit down and absorb the whole thing. It’s a novel (or movie) in song form, which in itself, is pretty impressive.


 # 6 – ‘Mississippi’ – ‘Love And Theft’ – 2001

Love And Theft’ was Dylan’s foray into the 2000s. The 2001 album provides a stark contrast to the dreary, depressing pastures of ‘Time Out Of Mind.’ It’s a fairly upbeat album, the first of a trilogy of blues-based projects. ‘Mississippi’ was a song written for ‘Time Out Of Mind,’ however, and it never properly made the cut. Instead, Dylan handed it off to Sheryl Crow, who had some success with it at the end of the 90s.

In 2001, Dylan came around to recording it for official release from his own camp. This, of course, resulted in the definitive rendition of the song. At the end of the decade when Rolling Stone was choosing the era’s finest songs, they had this to say about it:

“A drifter’s love song that seems to sum up Dylan’s entire career, and a rambling classic that ranks up there with ‘Tangled Up In Blue’.”

The theme of being America’s drifter is a recurring concept throughout Dylan’s work in the 2000s. One could argue this was him returning to form – the last time he was the country’s troubadour drifter was 1962 on his debut album. In both cases, his enthusiasm was undeniable. ‘Time Out Of Mind’ was clearly a painful album to make. ‘Love And Theft’ was probably a whole lot more fun.

# 5 –  Pay in Blood’ – ‘Tempest’ – 2012

‘Time Out of Mind’ was probably Dylan’s darkest album before 2012’s ‘Tempest.’ The former is a depressing exploration of post-relationship sadness. The latter, however, is a gruesome, murder-filled frolic through Dylan’s darkest musings. (Basically, the darkness fueling the two isn’t necessarily the same kind of darkness.) ‘Pay in Blood’ is the epitome of the album’s thematic nature.

‘Pay in Blood’ is home to imagery of firing squads, chaining people up, ordering dogs to tear enemies limb from limb, and so on. “You get your lover in the bed,” Dylan croons. “Come here, I’ll break your lousy head… I pay in blood, but not my own.” It’s clear that Dylan, as usual, is embodying a fictional persona to convey his story. There’s something about its unbelievable passion that’s so perfect, though, and it bombastically pushed Dylan into yet another era of his career.

(Of course, we’ve yet to see what becomes of ‘Tempest’ and its themes. ‘Shadows in the Night’ and the upcoming ‘Fallen Angels’ took the torch and ran in the opposite direction, which is very Bob Dylan.)


 #  4 – ‘High Water (For Charley Patton)’ – ‘Love And Theft’ – 2001

‘High Water (For Charley Patton)’ is a perfect example of how Bob Dylan pulled influence from very early Americana to craft his songs of the era. The track on its surface is a recounting of a famous Louisiana flood, one inspired by a song penned by the great Charley Patton in 1929. Beyond that, however, one will find that Dylan crafted the lyrics with aid from Robert Johnson’s lyricism and traditional American arrangements.

‘High Water’ has become a staple of Dylan’s performances since its release; he still performs it pretty regularly on the Never Ending Tour. While the banjo-driven release from 2001 is spectacular, it’s worth noting that a (potentially) superior version does exist. The electric live rendition from the 2003 tour can be heard on ‘Tell Tale Signs,’ and it’s a complete powerhouse of intensity.

“Well, George Lewis told the Englishman, the Italian, and the Jew – You can’t open up your mind, boys, to every conceivable point of view. They’ve got Charles Darwin trapped out there on Highway 5; judge says to the high sheriff – I want him dead or alive. Either one, I don’t care. High water everywhere.


# 3 – ‘Long and Wasted Years’ – ‘Tempest’ – 2012

‘Long and Wasted Years’ is a track that seems very autobiographical amidst the carnage of ‘Tempest.’ Dylan doesn’t kill anyone, or bang their head in, or send them off on the Titanic. Instead, he wanders about a scene of misery and self-doubt. He has no family, no loved ones, and recounts a relationship gone so far awry that he considers its years ‘long and wasted.’ Analysis of the song varies. Some have aligned it in a biblical context, others think its about an old relationship Dylan never properly pursued or cared about – perhaps with Joan Baez.

The deeply personal aura of ‘Long and Wasted Years’ makes it somewhat doubtful that’s fully fictitious, though Dylan would likely chock it up to that if anyone was to ask him. There’s even veiled references to his own persona – “I wear dark glasses to cover my eyes; there are secrets in them that I can’t disguise.” Whatever the case, it’s a poignant piece of Dylan’s catalog that stands out on ‘Tempest’ powerfully.


# 2 – ‘Workingman’s Blues #2’ – ‘Modern Times’ – 2006

‘Modern Times’ is the middle of the aforementioned ‘trilogy’ of music Dylan put out in the 2000s. It’s home to so many classic songs that could earn a place at the top of this list: ‘Thunder on the Mountain,’ ‘When the Deal Goes Down,’ or ‘Someday Baby,’ just to name a few. The cake, however, must be taken by ‘Workingman’s Blues #2.’

‘Workingman’s Blues #2’ may be the last time Dylan actually got political with his lyricism. He recounts the painful struggle of an American blue collar worker who can’t find work in an evolving country. The plight of the proletariat is front and center, marked emotionally by Dylan sampling his chorus from the 1946 jazz standard, ‘June’s Blues,’ performed by June Christy.

The composition of ‘Workingman’s Blues #2’ is the most breathtaking aspect of it. It’s structured to perfection. It elegantly transcends even some of Dylan’s most impressive compositions with a unforgettable piano performance. Every element of the song syncs in harmony beautifully. The vulnerability of the song’s lyrics match that beauty, making it quite the distinguished hidden gem on ‘Modern Times.’

“In the dark I hear the night birds call; I can hear a lover’s breath. I sleep in the kitchen with my feet in the hall. Sleep is like a temporary death.”


# 1 – ‘Things Have Changed’ – ‘Wonder Boys Soundtrack’ – 2000

While ‘Love And Theft’ was Dylan’s first full record in the new century, it was preceded by the single ‘Things Have Changed,’ which was written for ‘Wonder Boys.’ It later snagged Dylan his much deserved Oscar for the year’s best original song in film. The movie was a perfectly fine Michael Douglas dramedy with Tobey Maguire, back when the latter could still find work in Hollywood. More importantly, it was a vehicle to bring ‘Things Have Changed’ to life.

‘Things Have Changed’ stands on its own without ‘Wonder Boys.’ The song is Bob Dylan planting his flag in the twenty-first century. The world was a new place sixteen years ago, and Dylan acknowledged that. He adapted his style, as he always had, and progressed forward with the fervor of a man thrice his junior.

‘Things Have Changed’ is the declaration of a man aware that the world is no longer the place it was when he ruled it. The best part of the entire song is that he simply does not care. It doesn’t matter that “things had changed.” Dylan was still Dylan and he was growing stronger with each release of new music after ‘Time Out Of Mind.’ The track is a grand shoulder shrug to potential obsoleteness, to which the world responded by quickly handing Dylan an Oscar and lauding his continued success as an older artist.

‘Things Have Changed’ proves that even though Bob Dylan gets older, his music doesn’t. It proves that the harsher his voice gets, the more ardent he becomes. He’ll never be a relic – even when he’s gone. His songs will be the sharpest written tunes this side of 1962 forevermore.

The most wonderful thing about that? It’s a legacy that keeps on giving. (Here’s to ‘Fallen Angels’ on May 20!)

“People are crazy and times are strange. I’m locked in tight; I’m out of range. I used to care, but things have changed.”

Updated Nov 11, 2020

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