In honor of Bob Dylan’s 75th birthday: 5 deep cuts all fans need to hear

Bob Dylan Real Live vinyl

Tuesday is Bob Dylan’s 75th birthday, and it seemed wrong to not feature some sort of content about my favorite musician. Instead of reviewing Fallen Angels or writing a long column about the impact he’s had on my life, I thought I’d keep things simple and just share a few songs that the average Dylan fan has possibly never heard.

Dylan’s fanbase is so devoted, of course, that most serious fans already know these songs by heart like I do. But just in case you like the man’s music, but never got around to getting completely obsessed, these are five deep cuts that you really need to hear.

1. “Moonshiner”

“Moonshiner” is an old folk tune that has been traced back as far as the 1930s. Dylan recorded his version back in August 1963, but for whatever reason, it didn’t make it on to The Times They Are A-Changin’ in 1964.

It certainly deserved a spot on the album, though; Dylan’s performance here is simply phenomenal. His fingerpicking sounds as good as it ever did, and the way he stretches out some of the words adds an extra layer of drama and intrigue to the song’s fairly straightforward lyrics.

This is one of those tunes that can really mess with my emotions. If I’m driving late at night and this comes on, it might make me feel sad. If I hear it and I’m at home in a good mood, it might just make me feel inspired to pick up the guitar and harmonica and do my best Bobby D impression. No matter what I’m doing, though, if this comes on, I’m going to have to listen to the full thing. There’s no turning off “Moonshiner” halfway through. Not for me, at least.

“Moonshiner” did eventually see a commercial release in 1991, when it was included on The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991. It’s one of that compilation’s many essential Dylan deep cuts and remains one of my favorite tracks from his early folk years. If you like listening to young Bob, make sure you check it out! 

2. “Last Thoughts on Woody Guthrie”

This song isn’t even a song at all—it’s a poem. Dylan recited it one time, at New York’s Town Hall in 1963.

“There’s this book coming out, and they asked me to write something about Woody,” Dylan says at the beginning. “Sort of like, ‘what does Woody Guthrie mean to you in 25 words?’ And I couldn’t do it. I wrote out five pages, and I have it here … I have it here by mistake, actually, but I’d like to say this out loud.”

He goes on to speak for nearly seven minutes, and it’s powerful, thoughtful stuff from start to finish. Here’s the opening lines:

When yer head gets twisted and yer mind grows numb/ When you think you’re too old, too young, too smart or too dumb/ When yer laggin’ behind an’ losin’ yer pace/ In a slow-motion crawl of life’s busy race/ No matter what yer doing if you start givin’ up/ If the wine don’t come to the top of yer cup/ If the wind’s got you sideways with with one hand holdin’ on/ And the other starts slipping and the feeling is gone …

The whole thing is like that. I’m listening to it now for the first time in a few years, and it’s hitting me all over again. This is a side of Dylan that didn’t come out very often, but I’m certainly glad it did on that one night in 1963.

Read the full poem here.

3. “Tell Me, Momma” (live, 1966)

Dylan’s performance at the Manchester Free Trade Hall in 1966 is the stuff of legend, and Columbia released it in 1998 as The Bootleg Series Vol. 4: Bob Dylan Live 1966. It was in the middle of his famous tour of Australia and the UK with the Hawks, when a certain segment of fans were upset Dylan had “gone electric” and started playing loud, unapologetic rock and roll. (This was the night a fan famously called Dylan “Judas,” and Bob reacted by telling the Hawks to, play fucking loud!)

The whole concert is outstanding, but “Tell Me, Momma” has always stood out to me. It’s a Dylan original, but he only played it during this tour, and a lot of the lyrics are impossible to understand. It’s raw, mean, and Dylan absolutely annihilates the audience. You have to hear this one to believe it, friends.

4. “Tangled Up in Blue” (live, 1984)

“Tangled Up in Blue” is far from a deep cut, I know, but I have always loved this version from Real Live, which was recorded during Dylan’s 1984 European tour.

On this version of “Tangled Up in Blue,” Dylan changes the lyrics, the arrangement, and the chords, but it works beautifully. Just check out that first verse, which builds and builds until Bob finally belts out, Taaangled uup iiiiiiiiiin bluuuuuuuuuuuue!

Is this better than the original version? No, of course not. But it’s a completely new take on one of the man’s three or four best songs of all time, and I can’t recommend it enough.

5. “‘Cross the Green Mountain”

Gods and Generals was a civil war film that came out in 2003. It was not very good. At all.

I know this, of course, because Bob Dylan recorded an original song for the soundtrack, and that simple fact was enough to get me in the theater.

As bad as that movie was, though, “‘Cross the Green Mountain” is flat-out excellent. It’s one of Dylan’s very best late-career masterworks, up there with “Thunder on the Mountain,” “Beyond Here Lies Nothin,’” or “Long and Wasted Years.”

Lyrically, “‘Cross the Green Mountain” looks at the war from the perspective of a plain, ordinary soldier. Musically, it’s more than eight minutes of guitar, strings, and rolling snares. It’s epic without being over the top; emotional without being too obvious.

And don’t worry—you don’t have to buy that soundtrack to own this song like I did 13 years ago. It was included in 2008’s The Bootleg Series Vol. 8: Tell Tale Signs: Rare and Unreleased 1989–2006.

Stream all 5 songs below …