Ranking Bob Dylan's 21st Century Covers

2002-10-08, Memorial Auditorium, Sacramento, CA

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Photo by Duncan Hume

A few months ago, I came upon a fan mix called Dylan's "21st Century Cover Debuts," rounding up all the cover songs Bob first played from 2001 onwards, from “Humming Bird” (June 28, 2001) through “It’s a Man’s Man’s Man’s World” (November 7, 2018).

As longtime readers know, my main other musical interest is cover songs, so it was great having all Bob's recent-ish live covers in one place (or most of them - it was missing a few I added myself).

As longtime readers also know, I love a good ranking, and the more arbitrary the subject to be ranked the better! So I decided to rank all the new covers Bob Dylan debuted in the 21st century, from worst to best. 

Three caveats:

1. Many of the covers he first played live in the 21st century are, of course, the standards he recorded on his various Sinatra albums. I skipped those. The concert versions are pretty similar to the album versions, and I already ranked those.

2. I skipped some short instrumentals too.

3. Sticking with that cover-debuts framework, I'm judging each of these songs by the first time they were played. I realize the first time Dylan performed something might not be the best time Dylan performed it, but it's a metric that puts all the songs on a level playing field, whether they became regulars or were one-offs. And, anyway, I didn't come across any covers that I knew would become great but sounded terrible the first time out.

Without further ado, here are the 32 [non-songbook] covers Dylan has performed for the first time in the 21st century, ranked. I’ve linked the ones I could find on YouTube (paid subscribers, go here to download the full set).

32. The End of the Innocence

Originally performed by: Don Henley
First time played: October 8, 2002 in Sacramento, California *
Times played: 9

Having just watched the epic Eagles documentary, I wanted to love this one, but ultimately Bob's nasal rasp sounds like some joker doing a "Bob Dylan sings Don Henley" impression. Maybe mauling “The End of the Innocence” was belated payback for an Eagle asking inappropriate questions backstage many years earlier.
* Note: Two different covers on this list debuted on this show 19 years ago today, which is why I picked today as the anniversary to run it.

31. Easy Lovin'

Originally performed by: Freddie Hart
First time played: April 18, 2003 in Dallas, TX
Times played: 1

Unlike many of the other one-offs on this list, there's no obvious reason Bob played Freddie Hart's 1971 country hit one dark day in Dallas. Hart had no particular connection to Dallas that I can find, and he hadn't just died or something. The best guess comes from Derek Barker's The Songs He Didn't Write book, and it's still fairly flimsy: Seven weeks before Dylan’s performance, bluesman (and the son of the Columbia producer who signed Dylan) John Hammond Jr. released a version on his album Ready For Love. Maybe Bob was spinning that CD on the tour bus? Either way, it's pretty forgettable. Even the usually reliable backing vocals of this era sound strained.

30. Lawyers, Guns, and Money

Originally performed by: Warren Zevon
First time played: October 5, 2002 in Eugene, Oregon
Times played: 4

As I said a few days ago writing about Dylan's four Zevon covers, the slow songs generally work better than the fast ones. "Lawyers, Guns, And Money" is one of the fast ones, and the least successful of the bunch by far, sounding more like Bob doing Zevon karaoke rather than finding his way into the song. That said, I wish Zevon karaoke really existed, and it's fun to hear Bob take a stab at one of Warren's funniest songs.

29. Return to Me

Originally performed by: Dean Martin
First time played: April 17, 2009 in Rome, Italy
Times played: 2

The Sopranos had one of the greatest soundtracks in television history (their use of the Rolling Stones' "Thru and Thru" to close season two is Mount Rushmore-tier music supervision). That run included a new recording from Dylan, covering this schmaltzy Dean Martin hit in 2000. He waited nearly a decade to perform it in concert, and it unfortunately wasn't worth the wait. This live version mostly serves as a showcase of how much his voice had deteriorated between 2000 and 2009. He should try it again in his current post-Sinatra vocal revival.

28. London Calling

Originally performed by: The Clash
First time played: November 21, 2005 in… hmm I wonder where
Times played: 2

Only played twice, and you can probably guess in what city. The band sounds killer, and Bob's having fun, but he only does a quick verse and chorus - it's more an extended intro to "Like a Rolling Stone" than a proper performance in its own right - so it's hard to rank it too highly.

27. It’s a Man’s Man’s Man’s World

Originally performed by: James Brown
First time played: November 7, 2018 in Augusta, GA
Times played: 2

Bob playing James Brown in Georgia is great on paper. The execution doesn't quite match the concept. He puts his all into it, but his "all," for whatever reason, doesn't seem to be all that much this particular night. His voice strains to hit some of the notes, removing it from greatness consideration.

26. Brown Sugar

Originally performed by: The Rolling Stones
First time played: October 4, 2002 in Seattle, Washington
Times played: 37

Maybe you had to be there. He performed “Brown Sugar” every night for a while and I'm guessing that, like the nightly "Not Fade Away"s he did a few years earlier, it was an absolute blast in the room. But just in the recording, hearing Dylan rasp through "Brown Sugar" is a fun novelty, but not something I'm going to dig out often. Plus this set of lyrics feel even more questionable today; even the Stones have stopped playing it.

25. Twelve Gates to the City (w/ Jim James, Jeff Tweedy)

Originally performed by: Reverend Gary Davis
First time played: July 15, 2013 in Toronto, ON
Times played: 1

During Dylan's awkwardly-titled Americananarama tour with Wilco and My Morning Jacket, Dylan sang three different covers with those bands' frontmen, Jeff Tweedy and Jim James. He tried two gospel tunes for one night each, before eventually settling on "The Weight." And while that's the obvious choice, “Twelve Gates to the City” shows why he landed there. It's a fun idea, but comes off like a bit of a mess (though the closing crowd singalong is a nice touch). Maybe with a few more tries they could have tightened it up, but it was promptly jettisoned.

24. Heartbreak Hotel

Originally performed by: Elvis Presley
First time played: August 16, 2009 in Stateline, NV
Times played: 1

Elvis Presley died on August 16, 1977. 32 years later to the day, Dylan worked a cover into his encore - and, appropriately, in the same state as Las Vegas to boot (albeit almost 500 miles away). Dylan's posthumous tributes often soar. This one remains firmly on the ground, but it was still a nice gesture.

23. Samson and Delilah

Originally performed by: Traditional
First time played: June 11, 2004 in Manchester, TN
Times played: 1

It says "Traditional" up there, but, really, this is basically a Grateful Dead cover. He has a long history of covering Dead-associated songs during the Never Ending Tour, though most came during the '90s.  This is one of the three country-ish covers Bob debuted during his Bonnaroo 2004 set. It starts a little slow but picks up energy; I particularly like the drums echoing lines like "he killed him dead!"

22. Yankee Doodle Dandy

Originally written by: George M. Cohan
First time played: July 4, 2009 in South Bend, IN
Times played: 1

I mean, can we really judge this seriously? It's as goofy as when he did that "This Old Man" cover (no, not the Neil Young song - we'll get to that - but the "he played nick-nack on his thumb" one). It’s the Fourth of July, he's having some fun, I'm all for it. I can't find any video, so I'll just assume he sang it doing jazz hands while high-stepping across the stage dressed like this.

21. The Weight (w/ Jim James, Jeff Tweedy)

Originally performed by: The Band
First time played: July 14, 2013 in Virginia Beach, VA
Times played: 4

Another one that's tricky to rank. On the one hand, hearing Bob cover The Band (and not one of the Band songs he co-wrote) is great. On the other, using "The Weight" for this sort of all-star sing-along finale is clichéd, and Bob and co. don't really do anything with it that hasn't been done a thousand times before. So, of the three aforementioned James and Tweedy cover collaborations, I'm slotting it right in the middle. It was undoubtedly the most crowd-pleasing (I was in one of those crowds, and I was indeed pleased), but far from the most imaginative.

20. Blue Monday

Originally performed by: Fats Domino
First time played: November 23, 2005 in London, England
Times played: 1

Dylan's 2005 London stand featured a few cover surprises. We've already heard "London Calling," and he did a run at Link Wray's classic instrumental "Rumble" (so short I'm not ranking it), but the best of the bunch is easily "Blue Monday." Michael Gray's encyclopedia, which has a great entry detailing all the overlap between Bob and Fats Domino, makes the connection why The Fat Man might have been on Bob's mind: A few months prior, Hurricane Katrina had destroyed Domino's home, and he himself was missing for several days. He should have let them use this live version for the subsequent tribute album, like he did with Zevon's.

19. Suzie Baby

Originally performed by: Bobby Vee
First time played: July 10, 2013 in St. Paul, MN
Times played: 1

Well, this is about the sweetest story of this whole set (though the Zevon four-pack is close). In 1959, Dylan played piano in '50s hitmaker Bobby Vee's band. It didn't last long, but all these years later he still remembered. Here's what he said from the stage before performing “Suzie Baby” in St. Paul: "I've shared the stage with everyone from Mick Jagger to Madonna, but the most beautiful person I've ever been on stage with is Bobby Vee. He used to sing a song called ‘Suzie Baby'. Please show your appreciation with a round of applause. We’re gonna try and do this song, like I’ve done it with him before once or twice."

18. Humming Bird

Originally performed by: Johnnie & Jack
First time played: June 28, 2001 in Langesund, Norway
Times played: 24

Is it unfair to punish this cover for what it's not? Dylan show-openers rarely ever got better than the acoustic covers Bob did with Larry and Charlie on backing vocals. None are duds, but to me "Humming Bird" pales in comparison to the likes of "Hallelujah I'm Ready" or "I Am the Man, Thomas." I even prefer the other two Johnnie & Jack numbers Bob started playing around this time: "Searching for a Soldier's Grave" and "This World Can't Stand Long."

17. Get Out of Denver

Originally performed by: Bob Seger
First time played: March 16, 2004 in Detroit, MI
Times played: 1

Chronologically, this was the first one of these I remember happening. My first show was in Chicago a few weeks prior and, though that run was great, it was hard to compete with Detroit’s two shows: "Get Out of Denver" one night, a Jack White guest slot the next. This one's a hoot too; how often in the 21st century has Bob played a song this friggin' fast? It sounds almost like he's covering a Dead Boys song on the verses the way he sprints through the lyrics.

16. A Voice from On High

Originally performed by: Bill Monroe
First time played: August 15, 2002 in Hamburg, NH
Times played: 7

As I wrote about when diving into shows from 2000, Dylan got very into covering spiritual bluegrass numbers in the early 2000s. He waited until 2002 to bust out this Bill Monroe number, but it fits the mold perfectly. Interestingly, two weeks prior to this song’s debut, a concert reviewer in Worcester misidentified that show's opener "Humming Bird" (#18) as "A Voice from On High." Did Bob read the review and think, "Well, maybe I should do that song…"?

15. 1952 Vincent Black Lightning

Originally performed by: Richard Thompson
First time played: July 14, 2013 in Clarkston, MI
Times played: 1

An occasional subcategory in this list is "Bob covers his opening act." It happened with a Merle Haggard song we'll get to soon. And, a decade later, it happened with Richard Thompson, as, on the same Americanarama tour that generated the Tweedy/James duets, Dylan covered the man who had played three bands earlier. I've seen Thompson a few times and he's always played “1952 Vincent Black Lightning,” but Setlist.fm reports he didn’t play it in his own set that night, leaving it open to Dylan. The only bummer: Thompson missed it, having already hit the road to get to the next gig. The recording didn't surface for some time - it's still missing the opening line - and he said he at first thought people who told him were having him on.

14. Boom Boom Mancini

Originally performed by: Warren Zevon
First time played: October 4, 2002 in Seattle, Washington
Times played: 1

The clear winner of the two fast Zevon songs Dylan tackled - I guess that would make it the Ray Mancini to the Bobby Chacon of “Lawyers, Guns, and Money” (#30) - "Boom Boom Mancini" is a blast. Does it achieve the transcendence of the two slow Zevon songs he sang that fall? No, but he still should have brought it back more times than just the one.

13. You Win Again

Originally performed by: Hank Williams
First time played: June 11, 2004 in Manchester, TN
Times played: 2

I mean, it's Bob covering Hank. Can you really go wrong? The second of the trio of new covers debuted at Bonnaroo '04. The first was “Samson and Delilah” (#23), the last is still to come.

12. Let Your Light Shine On Me (w/ Jim James, Jeff Tweedy)

Originally performed by: Blind Willie Johnson
First time played: July 19, 2003 in Bridgeport, CT
Times played: 1

Of the three Americanarama trio covers, "The Weight" (#21) is undeniably the most polished. “Let Your Light Shine On Me,” like "Twelve Gates to the City" (#25), is a little messy. Yet it holds together better than that “Twelve Gates” did, and is much less obvious sing-along choice than "The Weight." Another try or two and they could have turned it into one hell of a finale. But I give it bonus points for creativity, and sounding pretty great even in a slightly sloppy first time out.

11. A-11

Originally performed by: Don Deal (though Buck Owens' version is better known)
First time played: March 11, 2005 in Portland, OR
Times played: 5

Bob first performed this song one night, performed it every night for a week, then never played it again! Go figure. Reportedly Buck Owens was in the house on this first night, even coming onstage during opener Merle Haggard's set, which presumably inspired the cover. The song is really a showcase for a duet between Donnie Heron's pedal steel and short-lived band member Elana Fremerman's violin. I've said before how I'm an Elana fan, and this is a reason why. This song benefits from the steel and fiddle interplay, which you stopped getting when she left. Bob's fine too, but they steal the show. (PS. I swear I did not even realize “A-11” landed at #11 until I completed my rankings, but it’s certainly appropriate)

10. Old Man

Originally performed by: Neil Young
First time played: October 8, 2002 in Sacramento, California
Times played: 33

Damn, in my memory I had "Old Man" as a song Bob did once or twice - not every night for almost two months! I also didn't remember it being so good. As is the case on a lot of these early-2000s covers, the Larry-and-Charlie harmonies elevate it.

9. Sing Me Back Home

Originally performed by: Merle Haggard
First time played: June 11, 2004 in Manchester, TN
Times played: 10

Fun fact about this song: Merle Haggard opened for Bob's spring 2005 tour. But he never sang one of his most famous songs. Why not? Because Bob laid claim to it for his own sets. Most nights he didn't play it, but the few nights he did, it was a high point. A shame he never once invited the original artist back onstage to join him.

8. Wait for the Light to Shine

Originally performed by: Roy Acuff and His Smoky Mountain Boys
First time played: October 5, 2001 in Spokane, Washington
Times played: 30

Another one of those acoustic cover openers, like "Humming Bird" (#18), and this one top-tier. This was the opening song Dylan played at his first show following the September 11 attacks. Though I'm generally wary of reading too much into Dylan setlist choices, I doubt coming back with a spiritual number of hope and uplift is entirely a coincidence. 

7. Shadows

Originally performed by: Gordon Lightfoot
First time played: October 9, 2012 in Edmonton, Alberta, Canada
Times played: 1

Chronologically, the first 2010s cover debut, which I discovered while putting together a comp of recent oddities and one-offs last year. Dylan is a big Gordon Lightfoot fan, even inducting him into the Canadian Music Hall of Fame in the '80s, and has covered his songs as far back as Self-Portrait. But "Shadows," supposedly performed by request (how the hell do you get a song request to Bob Dylan?) stands as high as any of 'em. He could have made this a nightly part of his set and I can't imagine anyone complaining.

6. Sad Songs and Waltzes

Originally performed by: Willie Nelson
First time played: June 20, 2015 in Mainz, Germany
Times played: 1

Dylan first rehearsed "Sad Songs and Waltzes" way back in 1980, in the same gospel-tour rehearsals that yielded a good chunk of the latest Bootleg Series. Sadly, this song was not included (he apparently went from this straight into "Somewhere Over the Rainbow" into the aforementioned Lightfoot's "If You Could Read My Mind" - how was this left threepack off the box set??). We had to wait another 35 years to hear Bob sing this song live. It was worth the wait.

5. Carrying a Torch

Originally performed by: Van Morrison
First time played: October 19, 2002 in San Diego, CA
Times played: 6

Was Fall 2002 the best ever period for live covers? It might top even the folk standards of the early '90s and the Sinatra numbers of recent years. I was surprised to learn this literal torch song was a deep cut in the Van Morrison catalog. Rolling Stone wrote the song "has the makings of a classic" when reviewing Van’s 1991 album Hymns To The Silence, but apparently Bob was the only performer who agreed.

4. Accidentally Like a Martyr

Originally performed by: Warren Zevon
First time played: October 4, 2002 in Seattle, Washington
Times played: 22

Bob mangles a few lines in this opening outing, but it doesn't matter one bit. As I said in that recent Zevon post, "Accidentally Like a Martyr" is one of Dylan’s definitive covers of the 2000s, and you can hear that even in the tune's slightly-shakier-than-average first outing.

3. Learning to Fly

Originally performed by: Tom Petty and the Heartbreakers
First time played: October 21, 2017 in Denver, CO
Times played: 1

This shouldn't be as good as it is. The micro-genre of "Bob sings classic rock radio staples" usually yields something like the way-further-down-the-list "Brown Sugar" (#26) - Bob-does-karaoke, basically. The easy armchair psychology answer to what makes “Learning to Fly” different is that one of Bob’s closest musical friends and collaborators had just died. I think there’s something to that, and it’s no surprise that each of the top four songs on this list are tributes.

2. Mutineer

Originally performed by: Warren Zevon
First time played: October 4, 2002 in Seattle, Washington
Times played: 31

The most-played of all Dylan's fall 2002 Zevon covers and, by a hair, the best. For those paying attention, you'll notice that thus far three of the last four covers are from Fall 2002. That was not intentional on my part, but I guess there's a reason Larry Campbell called it his favorite tour. Which brings us to the best cover he's debuted in the 21st century…

1. Something

Originally performed by: The Beatles
First time played: November 13, 2002 in New York, NY
Times played: 2

I was about to call this one of Bob's greatest one-offs ever until the internet reminded me that he in fact performed it a second time, seven years later, in Liverpool naturally. Nevertheless, this 2002 performance has that special something (heh). As Dylan says in the intro, the big Concert for George was coming up a few weeks later. Since he couldn't make it, he went ahead and upstaged everyone by delivering the best Harrison cover before the tribute show even began.

And that's it! Thanks for following along. Chime in in the comments with what you'd rank higher or lower, and become a paid subscriber for access to many, many more newsletters, as well as a download of this full set of 32 covers.

2002-10-08, Memorial Auditorium, Sacramento, CA