Bob Dylan Woodstock 1994: Drummer Winston Watson’s Backstage Story

Shock Naue Entertainment News brings you an exclusive insight into one of rock history’s pivotal moments and the years surrounding it, directly from the man behind the drum kit. Winston Watson, Bob Dylan’s drummer from 1992 to 1996, sat down to share his candid memories of touring with the music legend. His tenure covered some electrifying performances, including intimate club gigs, high-profile collaborations, MTV Unplugged, and the unforgettable Bob Dylan Woodstock 1994 appearance. Watson recounts joining the band mid-tour with zero preparation – not even having met Dylan before taking the stage in Kansas City – marking the beginning of a remarkable four-year journey. This period saw Dylan navigating the expectations of his legacy while continuing to forge his unique path, with Watson providing the backbeat. From the sophisticated Supper Club shows to the mud-soaked fields of Woodstock ’94, Watson offers a unique perspective on Dylan’s artistry and the realities of life on the Never Ending Tour.

Drummer Winston Watson discusses playing with Bob Dylan, including the memorable Bob Dylan Woodstock 1994 performance.

The Supper Club Intimacy: A Prelude to Bigger Stages (Nov 16-17 1993)

Before the massive festivals, there were the Supper Club shows, a stark contrast in scale and atmosphere. “The place was a speakeasy, like a private place for mob guys or something,” Watson recalls. “It was a dinner show; the stage was tiny. They made clothes for us, these oatmeal double breasted suites that I thought were pretty spiffy.”

The setlist adapted to the venue. “We did some pretty cool songs like “Jack-A-Roe” and stuff that wasn’t so raucous.” The experience left a strong impression on the drummer. “We did Letterman right after that. I just remember thinking, man this keeps getting better and better.”

These shows also attracted notable audience members. “Nirvana came to see us one of those nights. They were playing at Irving Plaza or someplace like that. Krist Novoselic and Dave Grohl were upstairs.” Watson even shared a small piece of gear history. “My drum tech had given Dave a pair of those sticks I later used on our MTV Unplugged, with the red tape on them. If you watch Nirvana’s Unplugged [taped the day after the Supper Club shows], Dave’s using those. I think those are the ones I gave him.”

Bob Dylan Woodstock 1994: Mud, Mayhem, and a Million Cameras

The Woodstock ’94 festival remains a standout memory, epitomizing the chaotic energy of large-scale events. “We were at a hotel in Albany near the airport,” Watson begins. “I met Nine Inch Nails, Cypress Hill and some other bands all raging at the airport bar. The Nine Inch guys thought I was in Cypress Hill, and the Cypress Hill guys thought I was with Nine Inch.”

Getting to the Saugerties site was an ordeal. “We go to the site the next day. It’s raining and it takes forever to get there. It takes so long that they bring food out to us, all stone-cold by then. At one point, they asked if we wanted to take the helicopter in. Everybody said no.” Despite the infamous mud, the band managed a clean arrival. “I never got one speck of mud on me. We changed into our stage clothes on the bus, got off, stepped on stage without getting any mud on us whatsoever.”

A candid moment backstage became unexpectedly public. “At one point, I asked Bob if he wants a cigarette. The two of us were smoking stage right, and I remember a million cameras clicking. I remember thinking, ‘Wow, I wonder who just showed up.’ I looked past his shoulder, and they were all pointed at us. That was pretty shocking.”

The performance itself, part of the Bob Dylan Woodstock 1994 legacy, felt impersonal due to the scale. “The stage was huge. I wasn’t near anybody. I hate those gigs. I grew up playing in bars. Even if you’re in an arena, I like my boys close. I know arenas make money or whatever, but I would rather do a multiple night stand in a nice theater. It was too big. Did anybody hear anything? I don’t know.”

Watson draws parallels with the original Woodstock’s sentiment. “Pete Townshend would say [about the original Woodstock], ‘Oh, I hated it. It changed my life, but I hated it.’ Yeah, I know exactly what you’re talking about, Pete. Not my favorite gig, but to have everybody you know from home call and tell you that they just saw you on TV, that was pretty cool.” The Bob Dylan Woodstock 1994 show, despite its challenges, undeniably became a significant televised moment in Watson’s career with Dylan.

Star-Studded Jams: Roseland ’94 with Bruce & Neil

Playing alongside other music icons was a frequent highlight. “I love playing with Bruce,” Watson states. “He and Neil Young are two of the loudest guitar players I’ve ever played with.”

When asked about Springsteen’s volume, Watson confirms, “Do you remember the legendary Roseland show where both of them got up on stage with us? Yeah, in ’94. They just played guitar; I don’t think they sang. That was as loud as MC5, most def. Solid as a rock too, man. Bruce is a great rhythm guitar player.”

These collaborations weren’t one-offs. “I was lucky to do that twice with him and twice with Neil Young. I think at Shore Line, Neil stepped on with us, and then we did a little thing somewhere in Germany, I think in ’95. Having him around was always fun because the two of them are really good friends.”

An even more significant pairing occurred in Finland. “The gig of gigs was when we played with Little Richard in Finland. That was awesome. The guy that I think is the originator, with the guy who is the originator. You don’t see that too often.” The experience was humbling. “We all sat stage left and watched Richard’s show. Bob and I looked at each other, like two students. Just like, ‘Man, what a band.’ It was the Jerry Hey horn section, like a church band, and they had moves. They were tight as a snare drum and Richard was just so, so great. It was almost embarrassing to go on the next night and do our show after seeing those guys. Bob felt the same way.”

Reimagining Classics: The MTV Unplugged Sessions

The MTV Unplugged taping presented its own set of dynamics, particularly concerning song selection. “There’s the show they released, and then there’s a whole other show that had no hits, nothing anybody would really recognize,” Watson reveals. “There’s this footage of us in our street clothes doing rehearsals and stuff, and he liked that better than the actual shows. We played all these stuff that wasn’t included in the final version.”

He points to readily available evidence: “There’s a really cool version of “I Want You” that’s been circulating on YouTube now. I’m surprised they haven’t got it off there. We’re in our street clothes. Again, it’s a rehearsal.”

Pressure from executives played a role in the final tracklist. “I think it was two nights. After we taped the first one, all the executives were complaining that there were no hits. No “Once upon a time you dressed so fine,” no “Everybody must get—” There was none of that. They were bent about that.”

Dylan eventually conceded. “At one point, Bob said, okay. The finished product is what happened. I think it’s a mixture of the two nights, but mostly the second night, I think.” Watson reflects on the decision: “It was a good idea in the end, I guess, but I thought the cool part about it is that we weren’t going to do that stuff. That was me being eager to see what he was capable of outside of that stuff. I don’t think the general public gave a shit what he was doing, aside from the hits they could tell their kids about or they did their dissertation on or whatever.”

He touches on the perennial challenge artists face with audience expectations. “Sadly, people don’t really want to remember you as you are, they want to remember you as you were. They have that embalmed memory of you.” When reminded that Dylan has fought this since the ’60s, Watson agrees, “Since day one. Wayne Kramer [of MC5] would tell you the same thing too. I mentioned that term I use, “memory embalmers.” He thought that was fantastic.”

Center Stage in Prague: Performing Without a Guitar (1995)

A series of shows in Prague in 1995 became legendary because Dylan performed without his guitar, a result of illness affecting both him and Watson. “Both of us were. We were so sick,” Watson confirms. “The joke was that I got Bob sick, but it was [from] the plane on the way over. I could just tell there was something. There were sick people on the plane and I could just tell. This was before they were scrubbing cabins. This is ’95, no one knew how filthy human beings were on airplanes. I got facetiously blamed for all that.”

Watson’s condition was severe. “As the day wore on, I think I called [tour manager] Victor Maymudes at 1:30 or something in the afternoon. I said, ‘Man, you got to come to my room. I don’t think I can make the show.’ Then I got in the shower, and I guess I didn’t come to my door. He had the porter open the door, and they found me in the shower passed out with the water running. I had a fever, I had thrown up my weight, basically. I was emaciated and dehydrated and all fucked up.”

Unbeknownst to him, the show was initially cancelled. “What I didn’t know is that they pulled the plug on the show. I had a reprieve because I was determined – even though I couldn’t stand up, I was determined to go and play that show. But there was just no way I could have done it. Just no way. When I found out that we had canceled the show and we had a day off, I actually could relax.”

He recovered enough for the rescheduled show, but challenges remained. “I was a lot better by the time we did our show the next day, but my throat was raw, my ribs felt like they had been kicked in.” Dylan’s decision not to play guitar added another layer of difficulty. “He didn’t play guitar, which kind of threw me for a loop. That’s what I was telling you about that rhythm. I would watch his right hand and the headstock of the guitar. As it would swing in a certain direction, I would know what to do. So I had to look for other cues. That took a minute to get used to.”

Playing through illness was tough. “And you’re still sick on top of everything else, trying to figure this out. I’m hoarse, I can barely talk to anyone and I still have a little bit of a temperature, but nothing has ever cured me faster than sweating it out in a rock and roll gig. For the next few days coming back was slow, but I was getting much better. We didn’t have any days off after that.”

Despite the rough circumstances, these performances gained notoriety. “Those gigs sound fairly rough for you guys, but they’ve become legendary amongst fans. People keyed in on that immediately. It became the thing of lore. It made the papers for sure.” Dylan’s stage presence changed too. “He had his moves, which I thought were cool. Anything he does that’s animated, or out of the ordinary, you’re going to want to see it. Especially when he speaks. Like any time he speaks onstage, that makes the paper. Isn’t that funny?”

On the Road with Legends: Touring with the Grateful Dead (1995)

The 1995 tour with the Grateful Dead offered unique interactions, particularly with Jerry Garcia. “I remember being one of the only people, according to Jerry’s crew, that talked to him during that period,” Watson shares. “[Longtime Dead roadie] Ram Rod told me that. I thought he was putting me on.”

The tour kicked off memorably in Vermont. “We had our first show with them in Highgate [Vermont]. They tore the fence down and came in, like Woodstock. That was cool.” Watson’s energetic drumming style drew attention. “I was notorious for breaking sticks… If I played lighter, Bob would’ve noticed that. He wanted me to play where I was at. During the first Dead show, I was chopping lumber like a beaver. Bob thought it was funny, because stuff was landing all over the place.”

This led to a curious encounter with the Dead’s crew. “The next day, we were soundchecking, and Ram Rod says, ‘Some of us in the crew want to have a word with you when you get a chance.’ I thought, ‘Oh fuck, what did I do now?'” Fearing he’d damaged equipment with flying drumstick debris, Watson prepared to apologize and pay for damages.

The crew’s concern was entirely different. “They look at each other and they start laughing. They said, ‘No, fuck all that. We want to know what you talked to him about.’ I said, ‘Who?’ ‘Jerry.’ Ram Rod says, ‘I’ve been with the guy longer than you’ve been alive. I haven’t said a word to him in 13 years. I want to know what the fuck you guys are talking about.’”

Watson found the situation amusing. “I thought that was the funniest thing. We didn’t really talk about anything! [Jerry] wanted to know where I grew up. I remember him saying that I looked so young… But we just talked about our lives and stuff every day.”

Garcia showed genuine concern when Watson suffered from exhaustion at RFK Stadium. “I actually fell out and had to be given oxygen. When I came to, my friend was there with me. Right next to him, I saw the beard and the glasses. He’s looking at the medic, serious as a heart attack. ‘Take good care of my man here. We need him tomorrow.’ I said [imitates wheezing]: ‘Don’t worry, Jerry…I’ll be fine…’ I thought that was pretty cool, that he actually cared.”

Their conversations often touched on music. “He just loved the fact that I loved doing what I was doing. It was such a charming thing to him to see the two of us playing together specifically… I said, ‘You know, we’ve been doing a few of your songs as of late. I never thought I’d have a chance to do that.’ He thought that was pretty cool.”

Regarding Garcia sitting in with Dylan’s band at RFK, Watson offers a surprising observation: “That Bob wouldn’t let him play! … I wanted to hear what I’d been waiting to hear. It kinda never came… Yeah! He doesn’t need to be doing Johnny Winter and Floyd Radford. As we were playing, I just remember thinking, ‘I hear your part, Bob. You going to let Jerry get in there?’ But it was obviously the thing they do as brothers… It’s like Bob was going, ‘Oh, yeah? Well, check this out.'”

Sharing the Bill: The Rolling Stones Encounter (1995)

Opening for The Rolling Stones brought its own moments of absurdity, particularly involving stage production. Watson recounts arriving at a venue with Dylan: “He’s on our bus, so we all get there together. We’re pulling up and he goes, “Looks like there’s some kind of big snake up there. What do you reckon that is?”

Bob Dylan backstage with Rolling Stones guitarist Keith Richards during the Voodoo Lounge tour era.

He was pointing to the massive cobra head stage set from the Voodoo Lounge tour. “I said, ‘I have no idea, man. It’s big, whatever it is.’ He goes, ‘Yeah…maybe we should get two of those.’ [laughs]” Watson appreciated the humor. “Like one is fucking ridiculous, but two would be— I think that’s just so absurd and funny. It’s like Stonehenge in Spinal Tap. First of all, it so over the top… To even joke about having two of them, I just think is funny.”

Memphis Moments: Mud Island and Future Stars (October 19, 1995)

A show at Mud Island in Memphis featured a diverse lineup and a notable backstage encounter. “The time we played at Mud Island, Taylor Hawkins was playing in Sass Jordan’s band and Percy Sledge opened for us. It was Sass Jordan, Beck, Percy Sledge, and then us,” Watson lists. He later connected with Beck about the experience: “I spoke to Beck years later, and he remembers security being really hard on him and his entourage, because they weren’t allowed to come say hi to us.”

Bob Dylan performing live on stage, captured during his intensive mid-1990s touring schedule.

The most poignant memory involves the late Taylor Hawkins. “Then Taylor became the Taylor that we all know and miss. I remember it like it was yesterday. The sun had already gone down. We were headlining, and I looked to my right, and there Taylor was sitting at the threshold of the stage watching our set. He wasn’t even with Alanis yet. He had just arrived.” Seeing Hawkins’ later success resonated deeply. “I’ll always remember that because when the Foo Fighters became what they are, I was like, ‘Wow, I can’t believe that’s the same guy who watched me play drums so long ago.’ Funny how this life goes, and now he’s gone.”

A Tour of Heroes: Hitting the Road with Patti Smith (1995)

Touring with Patti Smith was a personal highlight for Watson due to his admiration for her drummer. “That was one of my very favorite tours. I was in love with Patti’s drummer Jay Dee Daugherty. He was a hero of mine. The Paul Collins’ Beat, The Church – Jay Dee played with everybody. I got to watch their set every night and watch my hero Jay Dee work.”

The tour included memorable runs at iconic venues. “Those runs that we filled in at the Beacon Theater were a riot… That extra night was like, the stuff of legend. Probably some of the most fun I’ve had.”

This tour also forged connections that would resurface years later. “I would later go on to play with Oliver Ray, Patti’s partner and guitarist for like ten years… We saw each other 20 years later… We had a chance meeting… He waited the entire show to reintroduce himself after 20 years.”

This reunion led to further musical collaborations. “Me and Oliver, we’re in this band Saint Maybe. We played with them in Mexico City. We played at the Diego Rivera Museum, and Patti had never played Mexico City. It was awesome… We wound up jamming at Mexico City’s oldest punk rock club. Lenny Kaye came down and sat in with us, and we just tore the roof off the place.”

A Restless Farewell: Honoring Sinatra (1995)

Performing for Frank Sinatra’s 80th birthday celebration was another surreal experience. The song choice, “Restless Farewell,” was significant. “We rehearsed a couple other songs. “This Was My Love,” I think… But I think Frank liked [“Restless Farewell”] a lot. I could hear him saying ‘When’s that Dylan kid going on?'” The mutual respect was palpable. “When you watch it, you can see the genuine affection that both of them have for each other. Frank is looking at him and Bob was looking at Frank like he looked at Little Richard.”

Watson remembers the star-studded atmosphere and his distinctive attire. “I got to wear my Marvin Gaye suit. I was standing next to Tom Selleck who’s really big… He’s looking at my suit. It was lime green, I was wearing a turtleneck, the slip-on Billy Fury shoes… He’s like, ‘My, that’s some suit,’ in that voice of his.”

The backstage catering was extravagant (“like looking at a scene in Caligula”), and the guest list was a who’s-who of entertainment. “Anyone you could imagine was there, like Don Rickles, all the Rat Pack… Our table was really fun. I sat next to Bob. There was Frank and Barbara Marx, his wife… on the other side of him was Danny Aiello and Rickles. Then the table next to us, there was Patrick Swayze and Roseanne Barr and Johnny Depp and Kate Moss. It was like we were in one of those Hirschfeld drawings.”

The performance itself was hushed and impactful. “Actually doing that song, I didn’t have to do very much, just not make so much noise. Did you see just the way that they showed the crowd, watching us as we did the song? It was reverent. Everyone was moved by it. At one point when they cut to the audience, no one is saying a word, no one’s talking. They’re all like, really solemn… here I am in my Marvin Gaye suit just having a bit of fun.”

The audience’s reaction affirmed the band’s musical contribution. “It meant that musically, we had done our job, which I always felt we did in that band to the best of our ability. Even though some nights we didn’t get it right, I think no one would ever say that we didn’t try or that I didn’t give 110%.”

Conclusion: Reflecting on a Dynamic Era

Winston Watson’s time with Bob Dylan spanned a dynamic period marked by intense touring, high-profile appearances like Bob Dylan Woodstock 1994, intimate sessions, and collaborations with music royalty. His firsthand accounts provide a valuable glimpse into the workings of Dylan’s band during the mid-90s, showcasing the challenges, triumphs, and unique moments experienced on the road. From navigating unexpected illnesses in Prague to sharing stages with legends like Little Richard, the Grateful Dead, and the Rolling Stones, Watson’s perspective underscores the demanding yet rewarding nature of performing alongside an artist constantly defying expectations. His stories, particularly the vivid recollection of the mud, cameras, and sheer scale of Woodstock ’94, add a personal layer to these well-documented events, reminding us of the human experiences behind the music legends. Watson’s tenure highlights a significant chapter in Dylan’s ongoing musical journey, one defined by resilience, adaptability, and unforgettable performances.