60. Emma Swift – I Contain Multitudes / Queen Jane Approximately
As detailed in our feature “Every Time Bob Dylan Commented on a Cover of One of his Songs”, Bob once described how Grateful Dead frontman Jerry Garcia was capable of uncovering a layer of meaning in Dylan’s songs that even the songwriter himself was unaware of: “I would hear his versions of songs of mine and I’d say, ‘OK, I understand how it should go.’” With that in mind, it wouldn’t be a stretch to imagine Emma Swift’s album of Dylan songs, 2020’s Blonde on the Tracks, having a similar effect on Bob. Each track feels simultaneously familiar and completely new, a bit like turning a much-loved painting around to discover another equally brilliant painting on the back. It’s a remarkably consistent record, but the cream of the crop are the gentle “I Contain Multitudes” (released just two months after Dylan’s version) and the joyful “Queen Jane Approximately,” which was accompanied by a charming music video that featured Bob as the man in the moon. – Tim Edgeworth
59. Norah Jones & The Peter Malick Group – Heart of Mine
Anything Norah Jones sings becomes instant slow-dance material, and Dylan’s chipper and a little funky “Heart of Mine” is no different. By the end, “if you can’t do the time, don’t do the crime, heart of mine” just gets you right in the feels. Peter Malick gets his turn to shine too with plenty of guitar solo opportunities. They aren’t overdone; they provide interludes to just sway during. – Sara Stoudt
58. Richard Shindell – Señor (Tales of Yankee Power)
Street Legal is generally considered a disappointment compared to its immediate predecessors, Desire and Blood on the Tracks. But its best-known song, “Señor,” is an atmospheric track with appropriately Mexican/Spanish influences, filled with Mexican/Southwestern and biblical and apocalyptic imagery, which builds to a crescendo featuring Steve Douglas’ saxophone. (It also features drummer Ian Wallace, who may be the only Dylan/King Crimson crossover musician). In his 2007 cover, from the all-covers collection South of Delia, Richard Shindell, a fine songwriter himself who has lived for many years in Argentina, strips the song of all Latin influences, and performs it as a contemplative ballad, replacing Dylan’s anger with a sense of exasperation. – Jordan Becker
57. Willie Nile – Rainy Day Women #12 & 35
The original “Rainy Day Women #12 & 35” has such a distinct, classic feel, and Nile twists it into a George Thorogood-sounding cover. The guitar work is excellent, and the chorus of voices draws you in until you find yourself singing (or maybe shouting) along. Either version has a feeling of a singalong in a bar, but the energy is decidedly higher in Niles’s blues-rock cover. – Mike Misch
56. The Four Seasons – Queen Jane Approximately
In 1965, The Four Seasons released a cover album with the cumbersome title of The 4 Seasons Sing Big Hits…by Burt Bacharach…Hal David…and Bob Dylan. It was a fevered and cynical attempt to cash in on the burgeoning popularity of three wildly different things (that number includes the Seasons themselves) and as such is just plain weird. Side One featured famed Bacharach and David compositions like “Walk On By” and uh, “What’s New Pussycat,” while Side Two was dedicated solely to Bob. While the album is home to maybe the most terrifying version of “Don’t Think Twice…” ever recorded, it does feature a downright killer take on “Queen Jane Approximately.” Frankie Valli’s glorious doo-wop buzzsaw of a voice has rarely sounded better than it does here, imbuing the “Queen…” with a fierce, frantic and fabulously soulful vibe. – Hope Silverman
55. PJ Harvey – Highway 61 Revisited
It’s not immediately obvious that PJ Harvey’s “Highway 61 Revisited” is a cover of the 1965 Dylan classic. There’s no siren whistle, for one thing, and singer-guitarist Polly Harvey is strangely hushed on the intro, evoking Robert Johnson as a crudely recorded Mississippi blues musician on a crackly old phonograph record. The lyrics about God, Abe and the killing of a son sound kinda familiar, but not the violent interruption of fuzz guitar and thunderous drums.
Once you’re attuned, though, it’s clear that the no-nonsense PJ Harvey lineup of 1992, featuring Rob Ellis on bass and Steve Vaughan on drums, is key to a blistering reworking that justifiably found its way onto the 1993 album Rid of Me. With Steve Albini as engineer (don’t ever call him a producer!), the band transforms the song from a blues shuffle into an aggressive punk number that bursts with unvarnished emotional intensity. They take their cue from Pixies’ Albini-recorded Surfer Rosa in the track’s raw and unpredictable nature, with its distortion, explosive percussion, and sudden interlude of quiet. In the process, they do away with Dylan’s air of raucous satire and bring drama and urgency to his tale of reprobates making mystical bargains out on Highway 61. – Adam Mason
54. Lucinda Williams – Tryin’ to Get to Heaven / Masters of War (w/ Charles Lloyd & The Marvels)
One of the most haunting songs in Dylan’s canon, “Tryin’ to Get to Heaven” requires, demands, a certain world weariness, some tarnish to the precious metal. Lucinda Williams has this in spades, and on her cover of the song (from 2012’s Chimes of Freedom), she wrings the desperation out of the lyric. (She came back to the song during lockdown, sounding even more gloriously raddled.) “Masters of War,” of course, is a much older song, one that Lucinda has performed any number of times. Here she’s well outside her usual comfort zone of a country infused rock’n’roll, performing with jazz great Charles Lloyd and the Marvels. She comes on like Patti Smith with a very sore throat, wailing her mantra over a fairly free-form mash of Lloyd’s vintage jazz saxophony, Bill Frisell and Greg Leisz weaving their guitar and steel between the gaps. Unexpected and magnificent. – Seuras Og
53. Miley Cyrus – You’re Gonna Make Me Lonesome When You Go
Miley Cyrus has recorded and performed so many great covers over the years that it’s easy to forget there was a time not so long ago when it was still a novelty for her. Cyrus’s cover of “You’re Gonna Make Me Lonesome When You Go” came during an important transitional phase in her career. A year after her show Hannah Montana came to an end, and several months before she unleashed her fabled cover of “Jolene,” Cyrus released this quiet, acoustic country-rock gem on the 2012 Dylan tribute compilation Chimes of Freedom. Cyrus proved she was more than just a TV personality, emoting both sadness and joy as she rhymes “Honolul-a” with “Ashtabula.” It’s a great cover that serves as a prelude to her many fantastic covers to come. – Curtis Zimmermann
52. Esther Phillips – Tonight I’ll Be Staying Here with You
The soul singer Esther Phillips possessed a voice and interpretive gift that even Aretha Franklin stood in awe of. Like Aretha, Phillips’ contemporary and sometimes label-mate, the singer often embraced material outside the soul and R&B categories. She first turned heads with a cover of Lennon/McCartney’s “And I Love Her” (here’s a clip of Lennon himself introducing Phillips and praising her version). Over a decade later, she put a disco spin on a song from the 1930s, “What a Difference a Day Makes,” to land her biggest hit. A dip into the Dylan songbook was no surprise or stretch for Esther Phillips.
Her Dylan choice was an interesting one, the third single from Nashville Skyline project. Even though Phillips had released a country music album in 1966, her Dylan cover dispenses with the Nashville influence in favor of a Memphis or a New Orleans vibe. Honky-tonk piano and a tight horn section supports Phillip’s urgent reading of the song; her extemporizing on the fade out is particularly inspired. “Throw my troubles out the door, I don’t need them any more” may be the key line for Phillips, whose career became side-tracked more than once by her addictions and related troubles. You can hear both vulnerably and a survivor’s strength on this track. – Tom McDonald
51. Rise Against – The Ballad of Hollis Brown
Talk about angry! Chicago punk band Rise Against delivered one of the most furious Dylan covers ever with 2012’s “The Ballad of Hollis Brown,” recorded for the aforementioned Chimes of Freedom tribute album. No longer a folk protest song on acoustic guitar, as on 1964’s The Times They Are A-Changin’, it’s here a loud, full-bodied, fists-in-the-air epic, featuring a passionate and immense vocal from Tim McIlrath. It sees the group retell the tragic story of a South Dakota farmer so overwhelmed by poverty that he kills his family and himself, using it to highlight the mammoth scale of poverty and unemployment in Obama-era USA, almost 50 years later. What they do is make the issue a hell of a lot harder to ignore, especially when McIlrath hollers such lines as “The children are so hungry that they don’t know how to smile.” The band, indeed, make Dylan’s words speak again, and more powerfully than before. – Adam Mason
The list continues on Page 7.