I attended an online Bob Dylan lecture recently and looking for song suggestions that go beyond the obvious ones like Blowing in the Wind.
There’s no hard and fast rule as to what obscure means, maybe ‘deep track’ is a better word choice. Songs that aren’t covered by every guy in a pre Covid coffeehouse with an acoustic guitar.
I’m a big Dylan fan and know almost all of his work, also the whole Bootleg Series, so hundreds of outtakes, and my Dylan deep cuts are too numerous to mention, but here are some rather obscure ones I really like:
First, “Rambling Gambling Willie”, one of his first self-penned songs, a beautiful and funny topical folk song, and typical for Dylan as a song about a folk hero:
There’s a wonderful cover by Townes Van Zandt on “Roadsongs”:
Then there’s a not so obscure song, at least it was a regular album cut on “Street Legal”. It’s one of my favorite original Bob Dylan blues songs, with sexually blues innuendo worthy of the masters of the blues, “New Pony”. Sadly, there’s only a clip from a soundcheck in bad quality on youtube:
And to highlight the humor Dylan often showed, here’s “Bob Dylan 115th Dream”, one of the funniest songs I know:
Working man’s blues
Really classic stuff:
There’s an evenin’ haze settlin’ over the town
Starlight by the edge of the creek
The buyin’ power of the proletariat’s gone down
Money’s gettin’ shallow and weak
Not terribly obscure, but: Santa Fe. One of those songs that Dylan pretty much threw away/gave up on; whereas many fine songwriters would have blessed the muse for it.
And I have a great fondness for Talkin’ Clothersline Blues/Clothes Line Saga, but can’t find a video/audio of Dylan doing it.
Is Mama, You Been On My Mind obscure at all? God, I love that song.
j
Ah - here it is - Clothes Line Saga.
j
I am a big fan of “Love Minus Zero”.
Bob Dylan - Love Minus Zero (Audio) - YouTube
For my money, “As I Went Out One Morning” is the best song on John Wesley Harding. Fun to play too. It’s got a great whooping bass line.
Two 80s songs are among his best. “Jokerman”
and “Political World” .
For various definitions of “obscure.” It never gets air play.
Just saw an online ad which included his version of “If Not For You”. This was a big hit for Olivia Newton John, and I was not aware that he wrote it.
Dunno how obscure it might be but my favorite Dylan song is “Everything Is Broken” which supplanted my previous top favorite of “Tangled Up In Blue.”
“Isis”, “High Water (For Charley Patton)”, “Caribbean Wind”. I could go on…
Blind Willie McTell isn’t exactly obscure, but it’s only on a “bootleg” release. It has the reputation of being one of Dylan’s best. It is pretty great.
“Open the Door, Homer” is one of my faves, having first heard it on 1969’s “Hollywood Dream” by Thunderclap Newman.
Thunderclap Newman: Open The Door, Homer - YouTube
It shows up on “The Basement Tapes,” but to the best of my knowledge has never been covered by anyone else. I love the line, “Remember when you’re out there, trying to heal the sick, that you must always first forgive them.”
Not quite so obscure is “This Wheel’s on Fire,” since it’s been done by both the Band and the Byrds, and I’ve even heard Dylan himself perform it live. It’s a great song!