The 10 Best Bob Dylan Albums To Own On Vinyl

The Freewheelin’ Bob Dylan (1963)

Once you start doing a deep dive into Dylan’s catalog that makes it past the obvious albums and songs every retrospective issue of Rolling Stone recommends, there’s a lot of pleasure to be found in uncovering little gems — that are as incredible as the canonical stuff — on Dylan albums that are never on Best Song lists. “Blowin in the Wind” gets all the pub from this album, but when was the last time you listened to “Corrina Corrina?” That song is one of the best love songs Dylan ever performed, a moment when you can see how he could deconstruct and rebuild traditional songs from the folk tradition. Freewheelin’ is the first Dylan album where you can tell he was going to be someone incredible.

Another Side of Bob Dylan (1964)

When I was 18, I used to drive to my local public library and check out 25 CDs — the most allowed under the library’s rules — and copy them to my computer’s hard drive, in a quest to have all of the music I’d read about in record guides and music books and on the early days of the music writing internet. This was the only efficient way, since my folks didn’t get high-speed internet until I was 20 and I couldn’t raid Napster and Kazaa. At any rate, I had tried for multiple albums to “understand” or “appreciate” Bob Dylan, and nothing I tried made him appealing to me. I tried the five albums I mentioned in the opening here. I listened to them over and over as I delivered pizzas. I didn’t “get” Dylan. I resolved to check out five more Dylan albums and if I didn’t like them, to move on. I still remember how it felt like time stopped, that cold winter in my car delivering pizzas, the first time I heard “Spanish Harlem Incident,” the first Dylan song I ever really loved. I obsessively listened to Another Side for an entire eight-hour shift. It opened up Dylan to me. And for that, it’s remained my sentimental favorite Dylan album.

Blonde on Blonde (1966)

This is probably cheating based on the parameters I outlined above; this is probably the 6th most commonly owned Dylan album amongst people with turntables who also like Dylan; it’s double LP price can ward off casual Dylanologists. That said, this one — critically acclaimed, considered Dylan’s last masterwork not called Blood on the Tracks — still feels like it has tons of territory to uncover and enjoy, 50 years after it came out. Each listen can yield favorite new micro-moments. The way the harmonica comes in on “Stuck Inside of Mobile With the Memphis Blues Again.” The amplified anguish in the final verse of “Leopard-Skin Pill-Box Hat.” How “One of Us Must Know (Sooner or Later)” might be the most underrated song in the Dylan canon. For my money, this is the most essential Dylan album; his political and literature bending albums be damned.

Nashville Skyline (1969)

Dylan flirted with going full country on John Wesley Harding, but he goes all in on Nashville Skyline, an earnest country folk album Dylan recorded with a vocal patois he never used again; he sounds like a frog gurgling water for most of this, but that’s not meant as a negative. It’s just different. The songwriting on this is some of Dylan’s most tender, and most evocative; this is essential even without the seminal duet with Johnny Cash, “Girl from the North Country.” That Dylan dropped “Lay Lady Lay” — one of the only Dylan songs you can bone to — was just running up the score.

New Morning (1970)

One of the crazier narratives of Dylan’s career is how often he’s been written off as finished, and how often the “comeback” album narrative has been applied to his albums. But the guy never took five years off between albums until the mid-'90s; he never even went away. New Morning was one of the first Dylan albums saddled with the “Best since X album!” reviews, as critics turned off by his country experiments and his willful self myth-destruction on Self Portrait found a lot to love in Dylan’s slight return to folk rock on New Morning. The star here is “The Man in Me,” made famous years later when it was in The Big Lebowski, but the dalliances with barroom piano — “If Dogs Run Free” and “Day of the Locusts” especially — are what makes New Morning essential. New Morning lost out to Blood on the Tracks on the “Best Album Since Blonde on Blonde!” sweepstakes but it’s still a must own.

Planet Waves (1974)

Planet Waves is essential for including one of Dylan’s sneakily most known songs — “Forever Young” — but that’s not the only thing to recommend it by. It’s also the only proper studio album he ever made with the Band, eight years after they toured the world together pissing off Dylan fans by going electric, and a year before they’d release the live set Before the Flood and their Basement Tapes. The Band were on the verge of imploding, and Dylan was on the verge of retreating into himself to do Blood on the Tracks, but their stars aligned on this, one of Dylan’s loosest, most jocular albums. It opens with “On a Night Like This,” a rare Dylan song that sounds like a carnival soundtrack, and hits peak after peak with songs like “Hazel” and “Never Say Goodbye” and “You Angel You” and, of course, “Forever Young.”

Slow Train Coming (1979)

Because most people don’t want to talk about religion — for good reason; let’s keep that shit on Facebook, where it belongs — Dylan’s trilogy of Christian leaning albums from the late '70s/early '80s — Slow Train Coming, Saved, Shot of Love — are the most glossed over run of albums, apart from his albums in the early-'90s. Writing them off as misguided Christian rock — as a lot of people do — doesn’t capture how hard Slow Train Coming rules; it’s the first Dylan album with a gospel choir, and is, all things considered, his best blues-rock album. It’s like a warped version of Motown, with Dylan’s pinched vocals in the place of a rock vocalist. “Slow Train” and “Gotta Serve Somebody” are rare Dylan songs that kick ass, and for that this is a must own.

Oh Mercy (1989)

In late '80s, Daniel Lanois — producer for hip bands like U2 and a pal of Brian Eno — had a radical idea: he paired Dylan’s weathering voice and haunting lyrics with a dense fog of brushed drums and obtuse-angled guitar lines. The result was Oh Mercy, perhaps the most underrated Dylan album in his whole catalog, an album that boasts two of the most devastating Dylan songs in “Most of the Time” and “What Good Am I?” Ultimately, the album imagines a variety of alternate timelines where Dylan lets his albums be helmed by auteur producers who could have recontextualized him in interesting ways. This album was about it, as far as that goes.

Modern Times (2006)

An underreported part of Dylan’s sixth decade in music is not that he’s had to find increasingly creative ways to use his worn out voice; it’s that he’s often had to revert to the mode of his first album, and recontextualize and rework songs from the American songbook. His most recent albums have been Frank Sinatra covers, while his best album of the '00s, Modern Times, mostly reworked blues songs like “Rollin and Tumblin’” and “When the Levee Breaks.” This is the last Dylan album — at least to date — that rocks, kicking almost as hard as his stuff with the Band.

Shadows in the Night (2015)

Yeah, I’m throwing down the Infinity Gauntlet here: you need this Dylan album of Frank Sinatra covers from 2015 in your collection. The reasons are multitudinous: Dylan’s voice — never a trusty instrument — has morphed into a sound something like the inner thoughts of weathered oak barrels. He willingly deconstructs the idea of a “standards” album by doing a bunch of Sinatra songs no one remembers and then stripping them down to the point where these are minimalist masterpieces. It’s his quietest, broken album, in a discography of quiet, broken albums. It needs to be appreciated by more people than Dylanologists and AARP members.