Bob Dylan and… Willie Nelson – A Philosopher Poet

Aaron Galbraith

Before writing this article I assumed Willie Nelson would have had many interactions with Bob throughout the 60s and 70s and covered him many times on album and concert, but my (admittedly limited) research since would suggest that they didn’t start to really hit it off until the 80s.

Bob covered Willie Nelson songs several times throughout the 80s in studio outtakes and concert warm ups.

Popping up on the b-side of “Union Sundown” in 1983 was this fine version of “Angel Flying Too Close To The Ground”. It was the first Dylan 7 inch single I ever owed and it was a treat to turn over the disc and find this great rarity. Some great harmonica work for the harpist aficionados amongst us.


Here we have a great version of “Always on My Mind” from a 1984 tour rehearsal. For the record, I know Nelson didn’t write this but he had a big hit with only a few years prior and it has become a bit of a signature song of his.


And from the same year we have another rehearsal. This time it’s a version of “Why Do I Have To Choose?”


In 1985 came “Live Aid”. Dylan’s onstage comment “I hope that some of the money that’s raised for the people in Africa, maybe they could just take a little bit of it, maybe … one or two million … to pay the mortgages on some of the farms” was viewed as “crass, stupid, and nationalistic” by organizer Bob Geldof. However, Nelson along with John Mellencamp and Neil Young agreed with Dylan and were inspired to start “Farm Aid”. Dylan performed at the inaugural concert in September 1985.

In 1993 Willie released his 40th album “Across The Boardline” including his co-write with Bob on “Heartland”. You can read Tony’s review of the piece here.

Here is a wonderful live version from the pair:

Further on-stage collaborations came at Willie’s 60th Birthday celebrations. Here is “Pancho and Lefty” with both men in fine voice. Man, I love this version. Give it a listen.

Hey, did you hear Bob call Willie “A philosopher poet”. Quite a compliment coming from the “poet laureate of rock ‘n’ roll” himself!

In 2004 from Willie’s cable TV special “Outlaws And Angels” comes this duet of Hank Williams’ “You Win Again”. For some reason it didn’t appear on the accompanying album.


Given the size of Willie Nelson’s back catalogue I just assumed he would have covered Bob’s songs many, many times (I own only a small percentage of it, so I trawled his discography online looking for more – man, how I would love a career spanning albums box set, much like the Dylan “Complete Album Collection Vol. One” from 2013). Anyway, these are the ones I could find. Help me out if you are aware of any more.

Here is “What Was It You Wanted”, also from “Across The Boardline” in 1993. He also sang this one at Dylan’s “30th Anniversary Concert Celebration”.


Next up is “He Was A Friend Of Mine”. It appears on the “Brokeback Mountain Soundtrack” album in 2005 and whilst not strictly speaking a Dylan original, it is credited to him on the disc and in the booklet. I’ll include it here for the sake of completeness, and also because it is rather lovely!


Nelson’s next dalliance with a Dylan tune, comes from another soundtrack, this time from the 2007 “I’m Not There” album. Here he is covering “Señor (Tales Of Yankee Power)” with backing from Calexico. It’s one of my all-time favourite Dylan cover versions.


Moving on we have a funky version of “Gotta Serve Somebody” from 2008’s “Moment Of Forever”.


It’s a fine album in my opinion, it also includes a track called “The Bob Song” – which, unfortunately has got absolutely nothing to do with our Bob!!

In 2015 Willie teamed up with the great Merle Haggard for the duets album “Django and Jimmie”. Merle suggested they tackle a Dylan tune. They gave us this jaunty, bouncy version of “Don’t Think Twice, It’s Alright”.


Just recently they have both been on a bit of a Sinatra kick, Bob with his series of albums and Willie with his “My Way” album. I believe the only song common to both is “Young At Heart”. Here is Willie’s take.


Other songs both have covered during their careers include “Let It Be Me”, “Hallelujah”, “A Satisfied Mind”, “Precious Memories”, “Stardust”, “Winter Wonderland”, “Here Comes Santa Claus”, “Autumn Leaves” and “Corrina, Corrina”.


I thought I would end this article on another first for the Untold Dylan site. Here we have a recording by Englebert Humperdinck dueting with Willie on “Make You Feel My Love”. I’m going to assume Humperdinck has never been mentioned on these pages before! Anyway, this appeared on his 2014 album “Englebert Calling”. Willie’s voice and guitar was made for this song.


We have covered a whole series of articles on the theme “Why does Dylan like” and you can find some of them listed in the index.







  1. Really do enjoy both of their music that is mr. Willie Nelson and Mister Bob Dylan or Robert Zimmerman so now that I leave a message via a text the punctuation police are going to complain both of them speak to me in different ways very much like all types of music I missed quite a few people Johnny Cash and other artists that were taking away from us quite early much like Celluloid Heroes never really die I feel the same way about music that I’ve committed to memory and how it can make you remember what you were doing and at what time of the day it was sensory overload smells taste Visual and emotional and stimulating synapse

  2. Check out a great performance on YouTube of Willie and Bob singing Pancho and Lefty it’s awesome

  3. Hello there Tony, thank you for posting this interesting analysis…

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