Joan Osborne Recalls Singing with Bob Dylan and the Post-Jerry Dead

Plus re-recording "Chimes of Freedom" with Bob himself for a '60s-themed TV show

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In 1995, Joan Osborne covered Bob Dylan on her triple-platinum debut album Relish. Within a couple years, she was singing with the man himself, first in the studio duetting on a re-recorded “Chimes of Freedom” in 1999, and then onstage in 2003 as a member of The Dead, a post-Garcia incarnation of the Grateful Dead.

As that 21st-century version of Dylan and The Dead turns 21, I called up Osborne to talk all things Dylan—the various times she sang with him (in addition to all his Dead sit-ins, he invited her out for a few beautiful “Tears of Rage” duets during his own sets) and the various times she’s covered his songs, which led up to her excellent 2017 album Songs of Bob Dylan.

Before we get to the times you sang with him, the second track on your debut album is a Dylan cover. What's the story behind “Man in the Long Black Coat,” and why did you put it on Relish?

I was a huge fan of the Oh Mercy record. I still am. I was in Europe for the first time busking with a street band. I walked past a record store and saw the big display of the new Bob Dylan record, so I went in and bought it. At this time, it was cassettes. I popped it into this little red RadioShack Walkman that I listened to my music on and was walking around the streets in Paris listening to these songs. It was just so transporting.

“Man in the Long Black Coat” was very much speaking to me in that moment, because someone that I was close to I felt had fallen under the spell of a person who was toxic and manipulative. Despite friends and family trying to get this person away from this toxic guy, it didn't work. For me, the lyrics were hitting me in a very personal way. I think that's why I kept being drawn to it.

The cinematic aspect of the lyrics really does paint a picture, with the soft cotton dress on the line hanging dry and the bent-over-backward trees and all of that. It was just such a beautiful canvas, a visual landscape. I don't think it was a big stretch to associate that song with Appalachian songs, so I tried to pitch my voice a little bit towards that Appalachian holler when I was covering it.

I read you didn't grow up a super Dylan fan. You were turned off by the attitude of say “Like a Rolling Stone.” Were you a bigger Dylan fan by the time Oh Mercy came out?

I think it's not a big secret that there's a whiff of misogyny in some of Dylan's lyrics and some of his attitude. There are certain moments where you listen to him, and it really feels like he's punching down. Here's this genius artist, and yet he's lambasting some poor girl who rejected him. That part of it doesn't sit well with me. But you also can't deny that he's a great artist and an amazing songwriter.

I wanted to hear great songs, and I wanted to learn about writing songs, and he's one of the icons of the 20th century as far as that goes. So to just dismiss him out of hand because of these handful of songs that felt to me to be a little ugly, I just didn't feel like it was worth it.

This is a question that comes up again and again: Is there a place for you to be a fan of an artist that maybe has some parts of their character that are problematic? In Dylan's case, I felt like I could cordon that off and enjoy what I enjoyed about his work, which is incredible. I just felt like I would be cutting off my nose to spite my face to abandon listening to him at all because of this ugly flavor of a few songs.

I think your album is where I first heard “Man in the Long Black Coat.” Someone gave me a burned CD of Relish when I was in middle school. It had no liner notes, so I didn't know it was a Dylan song. Then a few years later, when I started getting into Dylan, I got Oh Mercy. I was like, "Oh, that's that Joan Osborne song."

Apparently my version of that song has sold a lot more than Dylan's version of that song on Oh Mercy, which is ridiculous in a way.

It’s funny you mentioned that, because the other song I wanted to ask is clearly better known through covers. You did “Make You Feel My Love” on your second album, a few years before Adele. You were early to that one.

I do think maybe Garth Brooks had covered it at that point, and Billy Joel, but hers was the biggest hit by far, I'm sure. I just loved the song. Dylan’s known, of course, for his political songs, and for his poetic writing and his surreal lyrics. I don't think that people give him enough credit for being such a romantic writer. The love songs that he writes are just heartbreaking, and that's only one of them.

We tried to do a very, very simple version of the tune. There's not a big string section on it or anything like that. It's just very bare bones. I think that, for me, that was the way to do it in that moment.

This came just after “Chimes of Freedom,” which is your first time actually working together.

It was probably the first time we met too. I think maybe I had opened for him for a show at Irving Plaza and might have had the very briefest of encounters with him at that point, but this was the first time that we were actually in a room together for any length of time.

How did that come about?

It was some sort of television show about the 1960s that couldn't pay for the actual version of “Chimes of Freedom,” or maybe wanted something newer, and I think reached out to Dylan's camp to ask about rerecording the song. They wanted him to do it as a duet. Maybe because they had heard my version of “Make You Feel My Love,” the people suggested me as a duet partner. It wasn't anything highly engineered. It really just fell into my lap.

I knew some of the guys in his band. I knew his drummer, George Receli, from this zydeco band called Loup Garou that used to play on the scene in New York when I was coming up. Larry Campbell had played on one of my records; I wasn't there in the studio that day, but I had met him here and there.

When I arrived in the studio, I guess I was either on time or a little early, and Dylan wasn't there yet, so I sat and hung out with the band. It was at a place called Sear Sound in the Hell's Kitchen neighborhood in Manhattan. My back was to the door, but I could instantly tell when Dylan walked in the room because the atmosphere, the weather in the room, totally changed. Everybody—not in an overt way, but in a very subtle way—their attention moved from whatever they had been doing, or whoever they were talking to, to Dylan.

You could tell that these guys had to be on point all the time, because Dylan was such an unpredictable character. They had to be ready for anything, and so there was this watchfulness. But he was friendly to me. I had just come from doing a tour with The Chieftains, the traditional Irish band, so I brought Dylan a gift of this very nice, expensive Irish whiskey, and I presented him with it. I said, “I don't know if you drink, but I brought you this from Ireland. Paddy from the Chieftains says hello.” He was like, “Well, I might drink this.” Then we got into working on the song fairly quickly.

There wasn't a rehearsal. We didn't go through the tune. We just got up on the mic. I had done a lot of work on my own so that I could come into the room and be ready. It's a good thing that I did, because there was no rehearsal. There was no, “Oh, Joan, why don't you sing this? Why don't you sing that?” We just started.

I don't know whether this was Dylan's choice, but we were on the same microphone. My face was just inches away from his face. I had to work around what he was doing, and what he did changed. We might have gone through it three or four times, and it was completely different from one time to the next.

What part was completely different?

The way that Dylan sang the song. His vocal phrasing, he played around with the melody, there were tempo shifts. He wanted to do it differently every time—which I can imagine, if it's a song that you've been singing for decades, you want to mess around with it. You don't want it to sound just like it did on the record. I think he, being this restless intellect, wasn't going to do that anyway. It was very challenging, and I had to be laser-focused. I was watching his lips so that I could match his phrasing.

I did a very basic one-third above what he was singing most of the time, and just tried to match him. You get into this entrainment where, when you're singing harmony with somebody, your voices come together and the sound waves lock together if the harmony is on pitch. In a way, it carries you along with it. So I tried to reach that moment of being in sync with him. I think it worked out pretty well. If you listen back to it, it sounds fairly assured. The phrasing is fairly connected, and we're singing in the same places and all that. I feel like I acquitted myself fairly well, but it was a little bit of a baptism by fire.

Of course, I was intimidated because there's Bob Dylan standing there inches from my face, but I couldn't allow myself to think about that. If I took up any mental space thinking about that, then I would probably flub the singing part of it.

Is it unusual to be singing into the same microphone in a studio setting? I think of that as a live thing. It looks cool, but makes it more difficult to mix, I would imagine.

Normally, if you're singing a harmony, you are on a different microphone. A lot of times, you're in a different room because if, for example, you do a perfect performance except for this one little spot in the chorus, if you're on separate microphones and you have separate mixes, then you can go back in and fix the three or four notes that weren't right and the rest of the part can stay. But he wasn't having it.

I found it surprising that he’d agree to re-record this ‘60s chestnut for a miniseries literally called The '60s. It seems like very un-Dylan thing to do.

Yeah. I wouldn't venture to second-guess why he decided to do it. Who knows? [laughs]

Do you remember any other interactions at that? You mentioned in a Times interview that the few things he said were fairly acerbic.

I just found him to be very funny in this deadpan way. The handful of times I've interacted with him, that's how I've experienced it. You can tell he's trying to play with you. He's trying to have some sort of a playful interaction. I have heard from other people that he likes the ladies, so maybe that had to do with it. Maybe he was flirting with me in a way, or just trying to connect in some way with somebody he was about to sing a duet with. Again, I don't pretend to know what his thoughts were.

Any specific examples stick in your mind all these years later?

I wish I could remember. I definitely remember that impression that I had that he was like tossing a ball at you and seeing if you can catch it. It was like he was trying to engage me in this playful way, and maybe even a testing way of, “Do you get this humor that I'm laying out for you?”

Let's zoom ahead a couple more years to The Dead era. Before we get to the Dylan side of that, can you run me through how you joined The Dead?

This was a handful of years after Jerry Garcia passed away. The four remaining members wanted to go out on the road, and they knew that they were going to need some additional musicians to fill out the lineup. At the time, my booking agent also represented them, and he was part of the discussions about who the other musicians might be. It was people like Warren Haynes and like Jimmy Herring. Instrumentalists, mostly, although Warren, of course, is a great singer too.

My name came up, and my booking agent said, “I really think this would be a great choice, because she can cover all these harmony parts, and she can lead on anything you want her to sing on.” Because of his suggestions, they flew me out to San Francisco. I think it was me and Warren Haynes. We did a show at the Warfield, just like an exploratory thing of like, “Would this work out if we decided to do this?” We did this show, and I learned a bunch of the tunes in advance that I would be expected to sing on. I sang some leads and some harmonies, banged a tambourine and danced around, and just did what you do at a Grateful Dead show.

That touches on a basic question I was about to ask, which is, you're up there just as a singer. There's a whole lot of any Dead show where there's no one singing. What do you do during a ten-minute instrumental jam?

You dance! You dance, you play tambourine. Just because you're not singing in that moment doesn't mean you're not still part of the band and you're not still part of the experience.

My thought at the time was that I was serving as a bridge between the audience and the band. I wasn't an original member; you could more likely look at me and see yourself up there. Like, “Look, she's dancing, and I'm out here dancing too.” I felt like I was this connector between these lofty individuals of the original band and the people out in the crowd. So yeah, that's what I did. I danced a whole lot.

I'm not deep into the Deadhead world, but was that community welcoming? Was it a good experience overall?

I was very nervous about that, in fact, and thought, “What are these people going to think? Who is this girl up here trying to sing these Jerry Garcia songs?” I was doubtful that it would go over. Ultimately, what I experienced is the vast majority of the fans were just so happy to see the band out again and to hear the music live again that anybody who was helping to make that happen was fine with them.

I loved singing those songs and got amazing response from the crowd. There were some versions of “Stella Blue” where you could just hear a pin drop. My voice is obviously different than Jerry Garcia's, or than any of the surviving band members. I think it might've been nice for some people to hear these songs reinterpreted in the way I did them. I wasn't taking them out into some super crazy different thing, because I was still performing them with the band, but I was putting my own spin on them and connecting with them as you have to when you're a singer. I can't go up there and try to imitate Jerry Garcia, because my voice is totally different. I had to find my way into the songs and do them the way that I felt like I could serve the song best.

For the most part, people seemed to really respond positively to that. I did hear rumors that some people in the chat rooms were complaining that I was shaking around too much up on the stage and that I needed to not dance so much. Whatever you do, somebody's not going to like it. I just ignored that and did what I was doing.

Then in terms of the Dylan portion of that tour, it's unusual. Dylan doesn't sit in with other bands that often. Certainly not every single night like he did for those couple weeks. Were there separate rehearsals with Dylan? For only eight shows, there were a ton of different songs that you all did together.

via bjorner.com

I remember a rehearsal that we did in one of the rooms at one of the venues. I think it was probably after our soundcheck. Bob Dylan brought up the things that he wanted to sing. “Alabama Getaway,” I remember, was one that he very much wanted to do. We just went through them informally with acoustic guitars and singing in the room. Then he would come out and perform them with us.

I'm sure that there were also times where they were just like, “Come out and join us on this,” but I was not part of those conversations necessarily. He talked to Bill or Bobby or whoever, and then I would look up and suddenly he would be out there.

You’re singing lead on a lot of The Dead songs, but when Bob's up there, there is a new lead singer: him. What are you trying to add to the mix when Dylan's singing?

If it's a song that's got harmonies, you're taking one of the harmony parts. If it's not, I think I might pick up a tambourine or do something like that.

There were moments when I did leave the stage sometimes during those shows. Not necessarily the Dylan ones, but if they were in the middle of “Drums > Space” or something, there wasn't much that I could do. For the next 15 minutes, rather than me standing up there feeling like an idiot, I would go and sit offstage and wait for them to signal that it was time for me to come back.

I watched all the existing videos of the sit-ins I could find, which are not great quality, but you are on stage for all of them. There's a “Señor” that's really good.

That's right. My part would be to do the call and response thing in the choruses, and maybe some “ooh”s or something.

Then a couple times you came on during Dylan's own set to do “Tears of Rage.” How did that happen?

I got word through the guys in the band. Larry said that Dylan wanted me to come out and join them on that tune. I didn't rehearse it with Dylan himself, but I went over it with the guys. Then they called me out on stage, and I performed that. I remember that, at a certain point, he just broke out into this huge grin after I started singing. Someone did take a picture of this. It just made me feel so good that I could make him smile like that.

Strangely enough, afterwards I was standing in one of the backstage hallways talking to my sister and her friend who had come to see the show. Dylan comes up to me. He had literally come from the stage; it was summer in Indiana, it was humid, and he was all sweaty. He was saying that he didn't love the lyrics of the song. They had always bothered him. He said, “I'm working on some different lyrics. What do you think of these?” He said this alternate lyric to me. As I'm standing there with my little sister and her friend, he's asking my opinion about him changing the lyrics to “Tears of Rage.”

I didn't know what to say or do. I was kind of like, “Yeah, those sound really great.” Then he went off back to his dressing room.

I gotta ask if you remember any of the alternate lyrics.

I do not. They might be on some of the recordings.

Did you have much other interaction with him offstage?

A little bit. What I came to learn is that his eyesight is very poor, and I think he doesn't like to wear his glasses, so what I discovered is that unless you are right within his field of vision, which is fairly close, then he doesn't necessarily know you're in the room. But there were a few times when we were backstage, and he had a little bit of a flirtatious energy. I walked past him, and he reached out and touched my elbow as I was going by, sort of like, "Hey, what's going on?" He was friendly towards me.

I wish I could remember chapter and verse every word that he said to me, but I don't think it was anything particularly monumental aside from that time that he came up and talked about changing the lyrics to “Tears of Rage.” It was like chit-chat and small talk. I got the impression that he—and this is just my conjecture, so it might be completely wrong—but I got the impression that he's an isolated person and he felt comfortable within this experience of working with The Dead, I think because he felt some kinship with Jerry Garcia and with these guys, some of the very, very few people in the world who have a similar status to him.

He's such a singular individual and his fame and his renown is so enormous and so unique to him that there's almost no one you could look to being at his level. He had tour managers and people like that around him, but he wasn't hanging out and shooting the shit and coming on the tour bus. I got the impression that he was somewhat isolated.

Did you ever hear the Dylan & the Dead album from the '80s, which is fairly poorly remembered?

They might have sent me a song or two from that, along with the massive amount of material they sent to me to learn before the tour, but I didn't search it out. I think what I've read about that tour is that people didn't think it was all that great. I think he was having a rough patch.

Before we move on to your own Dylan album, any other memories of that Dead tour?

A Grateful Dead gig isn't just about going to see musicians that you think are good. There's a whole community that the Deadheads have, and part of the show is just an excuse for that community to come together, and just a reason for them to be in the same place and to celebrate the band.

I would see these legendary characters out in the crowd. There was a guy who had some kind of a light-up swirling headpiece that he would put on, and then he would slowly make his way in between every single row of seats from the very back of the amphitheater to the very front. You would see this whirring colorful-lighted headpiece moving. You couldn't see the faces of the people in the audience past the first few rows, but you could see where this guy was, and you could track where you were in the night by how far he had gotten.

It was things like that. Looking at the people in the front rows and seeing how they would form into these small groups and go into the aisle, or go off this way or go off that way. You would walk around sometimes and see people not even within the amphitheater, but just off next to the bathrooms, and they would be doing some kind of group activity. I mean, I'm not a scholar about Deadhead culture, but for me, it was very, very interesting. You think of The Dead as like, “Oh, the fans are people who want to relive the '60s and they want to feel like they're back in the Haight-Ashbury and all of that,” and I'm sure that that's part of it, but I think it's also just they want to see each other and they want to be together. The music, of course, is very important, but it's not all-important. It's also about those people having space for their community.

You mentioned memorable Dead fans. Bill Walton just passed last week. I don't know if he was around during your era.

He was. I didn't hear that. I knew he was sick. Thanks for telling me. No, I didn't know. Yes, he would come around and-- what's the guy who took over from David Lee Roth?

Sammy Hagar.

Yes, Sammy Hagar would come and sit in sometimes. He and Mickey Hart were buddies. There were senators and people who would come and be fans backstage. There were probably a lot of very important people that I didn't recognize.

I don't know if he was a senator yet, but Al Franken is a famous Deadhead.

That was pre-senatorial career, but yes, he was around too.

Did you and Bob have any other interactions or overlaps post-Dead tour?

We've crossed paths here and there. We were on the same festival down in Birmingham, Alabama. He said hello to me as he was walking on the stage and I was walking off or something like that, but I haven't had any super earth-shattering encounters with him since then. Like I said, I think he's a fairly private, isolated person. He's not seeking me out. He did send me flowers once.

Was that tied to the Dead tour?

No. I think that might have been after we recorded “Chimes of Freedom” together. He sent me a huge, beautiful bouquet of flowers to thank me.

Many years later, you do your Dylan covers album. Why did you decide to do it, and why then?

It was something that had been on my mind for a while, this idea to do what Ella Fitzgerald had done in the 1950s, which is make a series of albums, now called the Song Book series, where she would pick a particular songwriter—Cole Porter, Duke Ellington—and devote a record to their songs.

I always thought, “Wouldn't it be cool to do something like that?” I'm not going to necessarily go and sing a bunch of Cole Porter songs, but to sing the songwriters that I consider the icons of my era. It had been in the back of my mind to do for a while.

We got a call from the Café Carlisle, which is this storied Manhattan cabaret room, and they wanted to know if I wanted to do a residency there. I thought, “I'm not going to go in and sing cabaret songs, and I don't really want to go in and just do my own material in this context. This is a perfect time to test out this idea, and spend two weeks digging into the songs of one particular writer.”

We thought about which writer should we choose. I thought about Leonard Cohen, I thought about Lou Reed, I thought about this one and that one. Bob Dylan just kept being at the top of that list. I had, of course, a bit of a history of covering his songs already. I mean, whenever you're listing great American songwriters, he's going to be at the top of your list.

Obviously a massive songbook. How do you pick which songs beyond the couple you've already done?

That's a double-edged sword. “Oh, great, we have all these songs to choose from!” And then, “Oh my God, how am I going to pick?”

Literally hundreds and hundreds to choose from.

Yes. You could do ten records of Bob Dylan covers and not run out of great material. For me, it was a lot of trial and error. Of course, there were particular songs I was drawn to just because I liked them: “Tangled Up in Blue,” “Buckets of Rain.” We would start there, then I would just try out different songs. You want something that is going to work with your voice. You’re not going to sing a Bob Dylan song exactly like Bob Dylan sings it. You want to find that place where your voice and the song intersect in a way that allows the song to blossom in a way that it hasn't before.

That's the whole point of covering somebody else's material: you try to bring something to the song that hasn't been expressed within it yet. You think about doing it like what a jazz singer does. They bring their particular voice to a song. Billie Holiday's going to sing a song different than Ella Fitzgerald's going to sing a song than Sarah Vaughan's going to sing a song. That was the guiding principle.

Is it true that Patti Smith is the one who pointed you to “Dark Eyes”?

Yes. Jack Petruzzelli, who I've worked with for a long time, was in her band at that moment. I was hanging out backstage at one of their shows talking with Patti and telling her about this project. She mentioned that this was a great song and thought that it would be good for the record. I believe she also has performed it live.

Yes, and with Dylan too.

Oh, wow. I knew she opened for him for a while. That was a song that I hadn't thought of, and we brought that one into the studio based on her recommendation.

Is the album essentially the same as the Café Carlisle setlist, or were there some songs that worked better in one format than the other?

There were some things that fell by the wayside. We learned and performed more songs at the Carlisle than we could fit onto the record. There's a version of “Gotta Serve Somebody” that we did, which is not on the record. Also “Don't Think Twice, It's All Right.” We worked that up, and then whatever the version was that we worked on in the studio ended up not being just the way I wanted it to, so we put that aside. That’s why you always want to go in the studio with more songs than you need.

One of my favorites, which is generally not a song I think much of, but your version of “Rainy Day Women.” Normally it's like, “Okay, I get the joke, ha-ha.” The way you do it makes me like that song more than when Bob does it.

I love his ballads so much, but I was trying to not have the whole record be super ballad-heavy. We were experimenting with some different things, and I thought, “Well, here's a chance to take a song that people know, but maybe let's do it in a way that it's going to take them 30 seconds to understand which song it is. Give it a little bit of a slinky vibe.”

Are there any Dylan songs you want to cover but still haven't?

“Shooting Star” is one. I really like some of the stuff from Rough and Rowdy Ways. It's so inspiring how he just continues to put music out there which is just so fucking good. It's so unique to him. There's a beautiful love song, “I’ve Made Up My Mind to Give Myself to You.”

That's the one I was just thinking of when you said Rough and Rowdy. It's in the vein of “Make You Feel My Love.”

What a song. What a fucking song. To have written just one song like that, I would be satisfied. I could say, “All right. I'm good.” To come out with that, at this point in his career, and just to be able to do that still, he's magic.

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Thanks to Joan Osborne for taking the time to talk! If you haven’t heard Songs of Bob Dylan, it’s one of the best Dylan covers records of recent years. And to hear a lot more of her with Dylan and The Dead on that 2003 tour, check out Jesse Jarnow’s excellent compilation and essay.

2003-08-05, Verizon Wireless Amphitheater, Noblesville, IN [Dylan set, ft. Osborne on “Tears of Rage”]

2003-08-05, Verizon Wireless Amphitheater, Noblesville, IN [Dead set, ft. Dylan on three songs]

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PS. As I mentioned a few days ago, I’m newly on self-imposed paternity leave, but the newsletters won’t stop. These are already scheduled and ready to go, so subscribe now to get ‘em sent straight to your inbox (note #2 and #3 will only go to paid subscribers). One or two guest Outlaw Tour dispatches will be slotted in too.