Switcheroo: Which Ten Bob Dylan Songs Should Frank Sinatra Have Recorded?

Among all the wonderful Frank Sinatra threads here are several devoted to Bob Dylan's new album, Shadows In The Night, which features performances of ten songs recorded by Frank during his long career. Off the top of my head, I came up with this list of Bob's own songs that I think Frank Sinatra could have (should have?) recorded himself. Please post your own choices.

It Ain't Me Babe
You're A Big Girl Now
Lay Lady Lay
Tonight I'll Be Staying Here With You
Watching The River Flow
Dear Landlord
Dark Eyes
Make You Feel My Love

(edit)
+ Forever Young
+ The Man In Me

 

Its hard for me to imagine Frank doing Dylan songs due to the verse verse verse verse and another verse style. Having stated that, I think Boots of Spanish Leather is one I can here. Or maybe One Too Many Mornings.

 

One Too Many Mornings - yes.

 

Idiot Wind
Positively 4th Street
Mississippi
Jokerman
Man In The Long Black Coat
Every Grain Of Sand
Ballad Of Frankie Lee And Judas Priest
If Not For You
Everything Is Broken
Dignity

 

- Idiot Wind - interesting choice...hmmm...
- If Not For You - yes!
- Dignity - perfect.

Thanks.

 

"If You See Her, Say Hello"

 

Tomorrow is a long time

 

Should I have limited the range of songs to the ones that Frank could have recorded before his passing in 1998? Or does that matter?

 

Most of the Time
Shooting Star
Not Dark Yet
If Not For You
Simple Twist of Fate

 

Things Have Changed

 

That one occurred to me, until I realized that Frank would probably never sing "I'm gonna dress in drag..."

 

Excellent choices. It's becoming clear that Frank could have recorded an entire box set of Bob's tunes.

 

Oh, this is a fun idea. I imagine him covering these like he covered "Mrs. Robinson" ("Jilly loves you more than you will know!"). Picture these tracks with the Sinatra treatment!

Tweeter & The Monkey Man
Jokerman
One More Night
Sad Eyed Lady of the Lowlands
Positively 4th Street
The Man in Me
You're A Big Girl Now
Tomorrow is a Long Time
This Wheel's On Fire
Hurricane ("...and to them black cats he was just a koo-kooky fella....nobody doubted that he shot the bank tella...")

 

That is too funny...

Great choices, but I am surprised that so many people can imagine FS doing Positively 4th Street -- the vitriolic Idiot Wind maybe, but "you've got a lotta nerve to say you are my friend?" I'll ponder that for awhile.

 

Simple twist of fate

 

He must have sung Mr. Tambourine Man, surely? I can practically hear him in my head.

 

Me too, but I'm still trying to get the William Shatner version out of my head.

 

I think it would have to be tunes that are strong on melody and not jammed packed with lyrics, verse after verse. "Mr. Tambourine Man" as mentioned above is a good choice. I would add some more obscure tunes, off the top of my head, "The Mighty Quinn", "Time Passes Slowly" and the not so obscure "I Shall Be Released".

 

Restless Farewell
Dark Eyes
Every Grain Of Sand
Señor
Sweetheart Like You


Peace and love✌

 

Ooops, I forgot to include Restless Farewell (I just mentioned it in a different thread.) Thank you.

And Senor -- yes! (Willie Nelson does a nice version of it, too.)

 

Just Like A Tramp Baby.

 

Just completely upend the meaning of the song - "Now I'm back in the rain baby, and you're on dry land!"

 

I'd like to hear Idiot Wind.

 

Sad-Eyed Tramp of the Lowlands
Just Like a Broad

 

A bump, and one more suggestion: Rainy Day Women #12 & 35, a/k/a Everybody Must Get Stoned.

"They'll stone you when you're standin' at the bar...they'll stone you when you're swingin' on a star..."