Bob Dylan and Willie Nelson: A Musical Timeline

Previewing this summer's Outlaw Tour

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Tomorrow night, Willie Nelson kicks off his annual Outlaw tour. This year, he’s bringing an old friend along for every single show: Bob Dylan. A big question on every fan’s mind this summer is, will they perform together?

They have quite a few times over the decades, having known each other now for over 50 years. It’s a clear mutual-admiration society. In Dylan’s latest book, The Philosophy of Modern Song, Nelson is the only person who gets two separate chapters—one for his and Merle Haggard’s version of “Pancho and Lefty,” another for his own composition “On the Road Again.” Dylan writes, “Willie Nelson could, as they say, sing the phone book and make you weep. He could also write the phone book…”

So, in anticipation of the tour, I wanted to look back at all the times they’ve sung together. Below, find an annotated timeline of their many collaborations. I’m limiting it to them actually working together, as opposed to covering each other or otherwise interacting from a distance, which would make this very long indeed (I did write about a run of Bob’s Willie covers in the ‘80s here).

1973: Bromance in Durango

The first time that Dylan and Nelson met, as best as I can figure, was in 1973 when Dylan was down in Durango, Mexico, filming Pat Garrett and Billy the Kid. In an interview, his co-star Kris Kristofferson recalled:

“[Dylan and I] spent a lot of time chatting in our trailers and I told him about my friend Willie Nelson. I asked Bob, 'Why isn't Willie famous? He's a genius.' So, the next day, Bob calls Willie up and gets him to come down to the set, and he made him play his old Martin guitar for ten hours straight. They ended up doing all these old Django Reinhardt tunes. It was fabulous.”

Reading this quote, I was skeptical of the details. Did Willie really haul his ass all the way to central Mexico, where they filmed the movie? Surely this meeting must have take place later in LA, when Dylan was recording the soundtrack. Right?

Nope. Joe Nick Patoski’s biography Willie Nelson: An Epic Life confirms:

After Dripping Springs and getting married, Willie rounded up a carload of pals to drive to Durango, Mexico, to watch Kris make a movie with Bob Dylan for filmmaker Sam Peckinpah… Willie ended up serenading the cast and crew all day long at Peckinpah’s house, gladly accommodating Dylan’s requests to hear more and more. “Dylan was a little shy, scared to death,” observed Willie. “They had him jumpin’ and runnin’ on them horses, and he ain’t no cowboy.” 

They apparently also hung out a few times shortly after the Durango filming, back in LA, though I can’t find much details beyond two intriguing entries in the 1973 section of Clinton Heylin’s Dylan-datebook A Life in Stolen Moments:

• Feb: Dylan attends a Willie Nelson session at the Atlantic Recording Studios with Leon Russell and Kris Kristofferson.

• Mar-Apr: In the company of Willie Nelson, Dylan attends a Waylon Jennings show at the Troubador [sic].

1976: Rolling Thunder Hits Houston

In 1976, Rolling Thunder came to Houston. Unlike the in-demand northern leg the previous fall, tickets on the southern leg moved slow. Some shows were cancelled, including one of two planned nights in Houston. For the remaining one, they brought in a ringer to help move tickets: Willie Nelson, making his lone star turn (get it?) on the Rolling Thunder tour. As Kinky Friedman put it to me in my book, “they had to call in Willie as a fireman to bail out Bob with the number of people in the crowd.” It helped somewhat, though the stadium was still less than full.

Gary Burke played percussion on the ’76 tour. We also spoke about this show for the book. Here’s what he recalled:

[Willie] showed up to do a double bill. It was like two French foreign legions showing up at this venue. We came with our semis and RVs, and he came with his semis and RVs. That show easily hit the six-hour mark. 

Before we went on stage, Willie came into our dressing room. Bob was there, and Willie introduced himself. Bob said, “What are you going to do tonight? Why don’t you do that thing about the stranger, the guy with the red hair.” I’m thinking, “Does he mean ‘Red Headed Stranger’?” 

There had to be 20-some-odd musicians on stage that night. Two bass players, three drum kits, a fiddler or two, God knows how many guitars. Somebody had a great idea, “Why don’t we do ‘Will the Circle Be Unbroken’?” As soon as they hit the first chord, it was like complete white noise.

At the end, someone went up to the mic, and said something like, “This has been a real long show, we appreciate you guys hanging out.” This one guy who was totally wasted, sprawled over some seats, just yelled, “Play all night long!”

Sadly, there is no recording of the Willie Nelson white-noise sit-in on “Will the Circle Be Unbroken,” their first public performance together. But to hear Willie’s own set that night, check out the soundboard tapes I recently unearthed.

1985: We are the ones who make a brighter day, so let's start golfing

Bob and Willie make two public appearances together in 1985. The first, and less consequential, was during the “We Are the World” sessions. Though they were only there among a million other superstars, there’s a great photo of just the two them talking:

I wonder what they were talking about…

Oh wait, I don’t have to wonder! Because reporter David Breskin observed the conversation. The answer: Golf.

Here’s Breskin’s fascinating report, from the book We Are the World: The Photos, The Music, and the Inside Story:

Bob Dylan and Willie Nelson stand next to the piano, discussing Nashville in the old days. “Nashville’s just like Hollywood now,” grunts Dylan. Out of the blue, Willie asks Dylan if he plays golf. Dylan seems slightly amused, replies, “No, I’ve heard you had to study it.” Huey Lewis, who’s been hovering on the edges of the conversations, takes this opportunity to plunge in with his ode to the links. He enthusiastically tells Mr. Bob Dylan, “There’s nothing to do on the road, but there’s always a great golf course. In Ohio, there’s hundreds of great golf courses. I just start whacking it around. I’m still awful, but it gets to be great fun. We throw a bunch of clubs in the bottom of the bus. You walk. You get outdoors.” Dylan, who doesn’t seem the outdoors type, follows up sincerely, “It’s relaxing?”

Huey: It’s as deep as you like.

Willie: You can’t think of hardly anything else.

Huey: [laughing] I heard a story where Willie came out and said the first hole of his golf course was a par 44, and said, “Well, I birdied it yesterday.” [laughing harder, Dylan doesn’t quite get it]

Willie: We play a lot of best ball, scramble.

Huey: That’s great . . .

Willie: [explaining to Dylan] Three of us play against another three, and if he hits the best ball, well we go play his ball . . .

Dylan: It’s real noncompetitive then?

Willie: It is, and yet in a way it’s more competitive, because you got a team against a team, so you really start trying hard. [Mind you, Stevie continues to play romantically behind all this, and across the room Bob Geldof is drawing a map of northeast Africa for Bruce Springsteen on a piece of sheet music, explaining the logistical difficulties of famine relief.]

Hanger-on: Ah, Willie Nelson on the metaphysics of golf . . .

Willie: Golf is my life . . .

Huey: [to Willie] Have you read Golf in the Kingdom?

Willie: Yes, I have. What a book.

Huey: Wow, isn’t it. “You are the ball.” It’s really true. Some shots man, you can just see them. They happen for you. And some, in the middle of the swing, you know it won’t work.

The moral of this golfing tale is that Dylan and Willie exchange private phone numbers and agree to do an album together. They tentatively plan to go to Hawaii during school spring break with the kids and begin working on the material.

“Tentatively” being the key word in that last sentence. If Bob and Willie recorded a duets album in Hawaii, it sure has been kept pretty quiet all these years. Maybe Bob was just saying that to get Willie and Huey to stop talking about golf.

They also appeared together on the classic LIFE magazine cover promoting the record, where Dylan looks like he’s wondering how he ended up with all these lunatics.

1985: “Wouldn't it be great if we did something for our own farmers?’

With all due respect to “We Are the World” (which is: not much), the duo’s second 1985 collaboration was much more significant. Over the summer, Dylan played Live Aid. It was a famously chaotic appearance, but one good thing came out of it. Onstage, Dylan asked an offhand question: “Wouldn't it be great if we did something for our own farmers right here in America?” Willie Nelson heard that and thought, “Yeah, it would be great.” 

Two months later, he founded Farm Aid.

Dylan played the first year. He was practically obligated to. His backing band was, for the first of many times, Tom Petty and the Heartbreakers (read my interviews with Heartbreakers Benmont Tench and Stan Lynch for much more on that). For half of the six-song set, they were joined by Willie as well. His presence is more ceremonial than anything; he never sings and I’m not sure his acoustic guitar is even plugged in. But still, a nice gesture.

1992: Bobfest in the “Heartland”

At the 30th anniversary tribute concert in 1992, better known as “Bobfest,” Willie was one of many stars on hand to cover Dylan songs at the Garden. He chose the most recent song of anyone there: “What Was It You Wanted,” off Oh Mercy, only three years old at that point. He’d already recorded it for his 1993 album Across the Borderline. It’s a beautiful and sensitive performance, a step above much of the greatest-hits karaoke elsewhere on display. That’s Don Was, their shared producer, on bass.

The day after Bobfest, Dylan was in the studio with Willie, recording his vocals on their co-written song “Heartland.” In an interview, Willie described how the writing process went:

Don Was, who knows Dylan, brought me a tape of the melody [Bob had] recorded, just him humming the tune with the word "heartland" every now and then. So I took the word and the melody and wrote a song around it… In fact, years ago, we joked about writing an album together. I'd write a song and send it to him and do it back and forth so I guess this is the end result of that.

When do we get the Bootleg Series release of that demo of Bob humming the song and occasionally mumbling “heartland”?

The song wasn’t originally planned as a duet, but, according to one contemporary news report, they “had such a good time at the Madison Square Garden tribute that Dylan joined Nelson in the studio the next day for the recording.”

I spoke to drummer Jim Keltner, who played on “Heartland,” a bit about it:

Willie Nelson and Bob Dylan are two of the most distinctive voices in the music business. You know immediately when they're singing, and to hear them sing together is beautiful. I love how they sound on “Heartland” together. I don't think they did enough of that. I wish they'd do it again. They're both here, man. They're both on this planet, still commanding all the attention they've ever commanded.

1993: TV Talkin’ Songs

The first public airing of “Heartland” came at a Nashville TV taping in January 1993, two months before Willie released his album featuring the recorded version, Across the Borderline. The show was called A Country Music Celebration, honoring the Country Music Association’s 35th anniversary (35th? Come on now). It featured Dolly Parton, Emmylou Harris, Vince Gill, and many more. For the occasion, Dylan donned a cowboy hat and an extremely loud jacket and did an extremely nasal “Heartland” with Willie:

Three months later, they’re back on TV again. This time, the occasion is Willie Nelson’s own The Big Six-O birthday special in Austin. Surprisingly, they don’t reprise “Heartland.” After Dylan does a stripped down version of Stephen Foster’s “Hard Times” off his recent album Good as I Been to You, Willie joins him for the Townes Van Zandt tune Dylan would rave about years later in The Philosophy of Modern Song: “Pancho & Lefty.” Bob had sung it scrappily at his own shows a few times in recent years, but this takes it to another level.

1997: Willie Nelson and His [Bob’s] Band

In 1997, Bob Dylan played five nights at Los Angeles’ tiny El Rey Theatre. Every night had a different superstar opener: Beck, Jewel, Sheryl Crow, and, the final night, Willie. Willie did his set backed by Tony Garnier, Larry Campbell, and Bucky Baxter from Bob’s band alongside his own harmonica player Mickey Raphael. It’s below if you want to check it out, Willie backed by one of Bob’s best-ever bands:

“Always on My Mind”

1997-12-20, El Rey, Los Angeles, CA — Willie’s set

Unlike Sheryl Crow the night before, who played accordion with Dylan, Willie didn’t sit in with Bob. So not a collaboration, but they were in the same building and hopefully got a chance to hang backstage.

2004: You Willie Again

Dylan rarely does TV appearances—unless Willie asks him. The occasion for this one was yet another Willie-honoring duets special, this time called Willie Nelson & Friends: Outlaws and Angels. Guests this time included Merle Haggard, Lucinda Williams, and Keith Richards (a great duet on “We Had It All,” which Dylan memorably covered in the ‘80s).

Dylan sings the Hank Williams tune “You Win Again” with Willie. Alas, his voice is pretty raspy, and his plonky guitar solo comes too early and lasts too long. Great on paper, but doesn’t quite come across (Willie sounds great though).

There’s also a funny video clip from the rehearsals. Terrible quality, but Bob’s wearing the same ridiculous blonde wig and knit cap he wore to the Masked & Anonymous Sundance premiere a year earlier.

2004/2005/2009: Play Ball

In the 2000s, Bob and Willie went out to the ballgame. Three different summers—2004, 2005, and 2009—they did tours together of minor-league ballparks (Bob did a fourth iteration without Willie in ’06). The first time, they played together a lot. The second, they played together once. The third, they didn’t play together at all.

They did four different songs together total. The first and arguably coolest—so of course it’s the one they only did once—was “Milk Cow Blues.” Dylan had recorded a version way back in 1962, but had only played it live once, in 1988. Willie had been performing it for years, and made it the title track of a 2000 album, which is probably why it was (always) on his mind. This rendition is based on his arrangement, with Nelson singing the opening verses and Dylan closing the song. A lot of it is people soloing.

After that one-off, they switched to more obvious fare for the rest of the tour. First was a song Bob has often used for guest sit-ins: “I Shall Be Released.” The chorus offers an easy sing-along even if someone doesn’t know the words. Willie does though, so he takes a few verses himself, as well as beautifully echoing Bob on the choruses. I miss the weirdness of “Milk Cow Blues,” but have no doubt this went over ten times better with the crowds.

Halfway through the tour, they dropped “I Shall Be Released” and started doing “Heartland.” Willie’s sons Lukas and Micah join him, as they do on most of these. These are the only Dylan concerts where he ever played it. It’s also the only one where I could find any video:

In 2005, they didn’t duet on any of the “normal” ballpark dates. But, when the tour came to Willie’s Texas home for the annual Willie Nelson Fourth of July Picnic, of course they had to do something.

So, just as they’d reprised their ‘90s duet “Heartland” the previous summer, in 2005 they reprised their ‘00s duet “You Win Again.” Unfortunately, it doesn’t go much better the second time around. Bob sounds like he’s losing his voice. 

Bob would crush this song today, with his much smoother Rough and Rowdy Ways voice. Maybe they should give it a third try this summer. We’ll soon see.

PS. Stay tuned on Saturday for a report from Outlaw Tour opening night in Georgia. Going out only to paid subscribers.