10 Times Bob Dylan Showed Up Where You Really Wouldn’t Expect Him

Just a few months after “We Are the World,” Steve Van Zandt assembled another large crew of famous musicians for a song. Their task this time wasn’t raising money, but convincing musicians to stop playing concerts at the South African resort Sun City. This should have been a no-brainer since this was the peak of apartheid, but everyone from Queen and Elton John to Rod Stewart, Linda Ronstadt, and Cher had appeared there in recent years. The song and video features cameos from Lou Reed, Bono, Hall & Oates, Keith Richards, Ron Wood, Herbie Hancock, Pete Townshend, Clarence Clemons, Bob Dylan, and many, many others. Dylan’s appearance comes at the halfway point when he walks down the street with Jackson Browne and sing a few lines of the song with him. It would have been great to see him interact with the Fat Boys, Afrika Bambaataa, and Kurtis Blow, but we’ll take what we can get.

If you wanted Bob Dylan to do something strange and out of character, the mid-1980s was the best time to ask. For whatever reason, this was a time when he was willing to do lots of interviews, even on television, guest on charity singles, do a choreographed dance move in one of his music videos, or star in a truly awful Rupert Everett movie. He also recorded this rapid-fire rap at the kickoff to Kurtis Blow’s 1987 single “Street Rock.” “I’ve indulged in higher knowledge,” he raps, “took scan of encyclopedia/Keeping constant research of our reports in news media/Kids starve in Ethiopia and we are gettin’ greedier/The rich are gettin’ richer and the needy’s gettin’ needier.” He agreed to do it because he borrowed some of Blow’s backup singers for a recording session. And in Chronicles, Volume 1, Dylan said Blow made him a fan of N.W.A., Run DMC, and Public Enemy. “These guys weren’t standing around bullshitting,” said Dylan. “They were beating drums, tearing it up, hurling horses over cliffs. They were all poets and knew what was going on.”

According to the typical narrative, Bob Dylan walked away from Judaism forever in the late Seventies when he embraced Jesus Christ and became a passionate Born Again Christian The truth is significantly more complicated, and the exact timeline is unknown, but he definitely returned to his Jewish roots in the early Eighties. If you need any visual proof of this, check out the numerous appearances he made on Chabad telethons in the Eighties and early Nineties. The 1989 one is especially memorable since he sings “Hava Nagila” with actor Harry Dean Stanton and folk singer Peter Himmelman, who happens to be his son-in-law. It’s so weird it almost looks like an AI video, but it’s real. This happened. (And what are Dylan’s religious beliefs today? Nobody knows, but it’s likely some unique fusion of Judaism and Christianity.)

By nearly any standard, the 1990 Dennis Hopper/Jodie Foster movie Catchfire is terrible. The thin plot revolves around a visual artist (Foster) who witnesses a mob hit and has to flee for her life. The only thing even remotely notable about it – beyond the fact that Foster’s next movie was Silence of the Lambs and Joe Pesci shot a quick scene the same year he made Goodfellas – is the fact that Hopper talked his longtime buddy Bob Dylan into filming a cameo. He’s creating a chainsaw statue during his brief scene, and his speaking voice is so mumbly that he’s essentially incoherent. (It makes renditions of “Desolation Row” circa 2013 clear and lucid by comparison.) The whole movie is so abysmal it makes Masked and Anonymous look like Casablanca.

When Wyclef Jean was lining up possible cameos for the video to his 1997 song “Gone till November,” he thought about reaching out to Bob Dylan. “No one really thought he would come,” Jean told the Herald-Tribune in 2018. “I remember people chastising me like, “Man, he don’t even show up for his son’s videos, so he’s definitely not coming to your video.’” But he showed up for a 15-second cameo seated next to Jean in an airport as Wyclef sings “I’m knockin’ on heaven’s door like I’m Bob Dylan.” “The only person he’d talk to on the set was me,” said Wyclef, ‘and he said, “Man, you’re such a cool cat, you remind me of my bass player that I played with.’ And it’s so funny he said that because one of my first instruments is bass, so it’s just crazy to me, like certain things that happen are just cosmic.”

In the world of Nineties sitcoms, Dharma & Greg is about as unmemorable as Caroline In The City, Veronica’s Closet, and Wings. Millions of people watched it back then since there wasn’t much else on TV, but we’d be willing to bet only a fraction of them could recall even the most premise today. (It starred Jenna Elfman and Thomas Gibson as a two polar opposites who impulsively married each other on their first date. There were 119 episodes across five seasons.) Its greatest claim to fame today is the October 12, 1999, episode Play Lady Play where Dharma plays drums in a friend’s teenage garage band. At the end, Bob Dylan appears out out nowhere to jam with her alongside T-Bone Burnett and other veteran musicians. It’s fantastically surreal, and it likely only happened because Dylan’s longtime buddy Eddie Gorodetsky was one of the writers. Friends and Seinfeld are watched and referenced roughly ten zillion more times today than Dharma and Greg. But then again, neither of those shows has a Bob Dylan cameo.

It’s tough being Bob Dylan. Sometimes you have to fly to Venice, hang out with Victoria’s Secret model Adriana Lima as she showcases the store’s newest underwear collection, and then accept millions of dollars for the inconvenience. Some fans were stunned when Dylan appeared in this ad, even though he allowed a Canadian bank to use “The Times They Are a-Changin’” in a 1996 commercial. But he telegraphed the move back in 1965 when he joked to a reporter that he’d let his music appear in an ad for “ladies garments.” It took 39 years, but the prophecy came true. And when Rolling Stone questioned Dylan about the move in December 2004, he was typically flippant. “Was I not supposed to do that?” he asked. “I wish I would have seen it. Maybe I’d have something to say about it. I don’t see that kind of stuff. That’s all for other people to see and make up what they will.”

At some point in nearly every interview with Gene Simmons, he mentions that he wrote a song with Bob Dylan. It sounds like a braggadocios fantasy, but this actually took place in 1991. It started with the KISS frontman simply calling Dylan’s manager and asking if there was any chance he’d be down for a songwriting collaboration. “And all of a sudden within two days, an unmarked van shows up at my house,” Simmons said, “and Bob gets out with an acoustic guitar in his hand, and tells his driver, ‘I’ll see you at the end of the day,’ comes up, and we start strumming. I mean, it was just like that.” Simmons broke down how they worked together in an interview with Billboard. “Bob came up with the chords, most of them, and then I took it and wrote lyrics, melody, the rest of it,” he said. “We understood each other right away. He picked up an acoustic guitar, and we just tossed it back and forth, ‘How ’bout this, how ’bout that?’’ They called their song “Waiting for the Morning Light,” and it finally came out in 2004 on Simmon’s solo LP Asshole.

In the real world, getting anywhere near Bob Dylan when he comes to town is simply impossible. In the magical world of Pawn Stars, all it takes is walking up to his bus tour with a vinyl copy of Self Portrait and asking for an autograph. Our bullshit detector went into overdrive when Pawn Stars star Chumlee pulled off this feat on the History Channel program. And when we called Chumlee up later that week, he stuck to the official story. “I found out he didn’t do that, so I scouted the grounds for about four hours,” he said. “He was shocked, but he signed the album for me. We talked for a minute and I told him I was a big fan of his work and my boss Rick would be really psyched if I got his autograph.” This was almost certainly a setup, especially since Rick appraises an unsigned Self Portrait at $50 when it’s worth a fraction of that. But staged or not, Dylan did indeed appear on an episode of Pawn Stars. (We await the day that Chumlee reveals the real story of how this happened.)

An underwear commercial with Adriana Lima was one thing. But a vocal contigent of Dylan fans flinched when he appeared in a 2007 commercial for the Cadillac Escalade, and then flinched again in 2014 when he shot another one for Chrysler. In both ads, he provided the narration (“You can’t import original. You can’t fake true cool…What’s life without the occasional detour?”) and even drove the car around. The Escalade commercial doubled as an ad for Dylan’s Theme Time Radio Hour on XM, and the Chrysler one emphasized creating jobs in America, but it wasn’t like Dylan did them for free. He was surely paid several million dollars. There may have been a stigma on such a thing years ago, but it’s almost totally gone.