Bob Dylan just keeps rolling along, touring, writing books, and occasionally releasing new music. Since 2000, Dylan has released five full-length LPs of new, original material. Incredibly, we’d argue that four of those five rank with his very best work. (Sorry, Together Through Life, you’re not quite there.)
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We’ve chosen one song from each of those records that possibly fell below your radar, especially if you haven’t been following along that closely with the new stuff. These tracks will give you excellent reasons to keep an eye on whatever Dylan does next, because there’s definitely going to be great stuff waiting for you.
“Lonesome Day Blues,” from Love and Theft (2001)
Maybe there’s something about the title that suggests this is just a pedestrian blues exercise Dylan cranked out without thought. But when you dive into it, you’ll likely be hooked. The music is as bruising as you’ll get from Dylan, as he took advantage of the talents of what was one of his finest assemblages of studio musicians. Meanwhile, the narrator piles up the tragedies of his life in front of us, which could be numbing in lesser hands. But then Dylan drops some funny one-liners and poignant observations (Yeah I tell myself something’s coming / But it never does) that keeps this thing surprising all the way.
“When the Deal Goes Down,” from Modern Times (2006)
Dylan likes to dip back into songs that he loved in younger days and repurpose their melodies. He then adds words that bring more modern songwriting honesty and intensity into this old-fashioned setting, and it’s always to great effect. On “When the Deal Goes Down,” he latched onto a tune made popular by Bing Crosby and turned it into a meditation on what it really takes to be an ideal relationship partner. Quite simply, it takes the inclination to be there for someone at their worst possible moment, just as you would be for their best. That’s heavy, but Dylan makes it sound boundlessly romantic here.
“This Dream of You,” from Together Through Life (2009)
Together Through Life received all the expected critical plaudits when it arrived in 2009, because it’s Dylan and we always expect his songs, even when they don’t initially blow us away, to keep revealing themselves to us. It’s fair to say this record’s reputation hasn’t improved much by time. But “This Dream of You,” the lone track for which Dylan wrote all the lyrics (the late Grateful Dead collaborator Robert Hunter did the rest), is a marvel. Its music possesses a sleek elegance, all the better for Dylan to play off it with the devastating heartache eating at the narrator.
“Long and Wasted Years,” from Tempest (2012)
We’re putting in our two cents for Tempest as the most underrated album of Dylan’s post-2000 output, which means there are several deep cuts we considered here. “Long and Wasted Years” is such a unique creation we just couldn’t avoid mentioning it. The structure is strange and alluring, as Dylan basically riffs on the same descending guitar figure, never bringing the thing to a chorus of any kind. He wails with regret about lost love and lost chances—that’s when he’s not reveling in the death of his enemies and quoting “Twist and Shout.” Wonderfully weird and sneakily affecting.
“Goodbye Jimmy Reed,” from Rough and Rowdy Ways (2020)
It’s a good rule of thumb that when Dylan includes a beloved blues musician in the title of a song, it’s going to be a real good one. When Rough and Rowdy Ways arrived, much attention was placed on the epics “I Contain Multitudes” and “Murder Most Foul,” which was understandable. But the album’s greatness also lies in those tracks where Dylan gives us a little melodic punch and lets his standout band sink their teeth into a groove. On “Goodbye Jimmy Reed,” you can hear Dylan enjoying himself as he barks his way through lyrics that muse on religion and reputation (his own, that is.)
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