A new volume of the long-running Bootleg Series came out recently, which means I found myself digging into some new-to-me Dylan music over the weekend. My poor wife, bless her, does not care much for mid-80s Bob Dylan (it is an acquired taste), and got really upset with me when she thought I was about to subject her to it yesterday (I wasn’t, in fact, because I know it’s not her thing and I’m not a complete asshole). But it did inspire me to create this week’s playlist, which is full of lesser-known Dylan songs that I really like. These are by no means unknown songs; I’m sure several of you will recognize several of these right off the bat. But they’re not usually going to appear on any best of or greatest hits collection.

1. “Girl From the North Country (Featuring Johnny Cash)”: Yes, Cash screws up and sings the wrong verse as the second verse, and yes, Dylan does that weird Nashville croon thing that he did for a while in the late 60s and early 70s. But this is still just a gorgeous read on this song.
2. “Blind Willie McTell”: The latest Bootleg Series features a full-band workup of this song, and while it’s a neat treat to hear, I still prefer this stripped-down, piano-and-acoustic-guitar-only version from Volume 3 of the Bootleg Series. It plays up the melodic relationship to “St. James Infirmary” more (by which I mean it’s just “St. James Infirmary” with different words), and Mark Knopfler’s guitar work is just beautiful.
3. “Just Like Tom Thumb’s Blues”: I’ve enjoyed playing this one on guitar for years (there’s even an old Youtube video of me doing it, if you’re so inclined), and the last verse, with its “I’m going back to New York City/I do believe I’ve had enough” just gets me every time.
4. “Isis”: Yes, the name is problematic these days, but back when this song was written (for 1976’s Desire), that organization didn’t exist yet. It’s a story of grave robbery, revenge, and love.
5. “Dead Man, Dead Man”: From the much-maligned “born again” series of albums in the late 70s/early 80s. This one’s a banger, if you ask me.
6. “Up To Me”: From Biograph. It’s an interesting story song, though I still think I prefer the Roger McGuinn cover to the original.
7. “Corrina, Corrina”: A subtle song from Dylan off of Freewheelin’. Yeah, I know Dylan’s usually about as subtle as a sledgehammer, but he manages to pull it off on this one. I like the faint drum and bass backing.
8. “When the Night Comes Falling From the Sky”: Empire Burlesque suffers from 80s overproduction, but this song actually makes it work. The over-processed drum and the synthy horn section really work for me.
9. “Song To Woody”: From his debut self-titled album. One of Dylan’s earliest originals, and still a sad, heartbreaking song.
10. “Where Are You Tonight? (Journey Through Dark Heat)”: I love this song primarily for the guitar solo at the end. Whoever’s playing lead on this one just tears it up.