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In the 1960s, Bob Dylan said that the only product that could make him sell out was “ladies’ undergarments.” Several decades later, he proved this was true when he appeared in an ad for Victoria’s Secret. Dylan has “sold out” several other times over the years, though. He does not seem like a celebrity who would appear in commercials, but he has, surprising his fans each time.

Bob Dylan wears a bolo tie and stands in front of a microphone.
Bob Dylan | Kevin Mazur/WireImage

1. Bob Dylan’s debut commercial appearance was for Victoria’s Secret

In 2004, Dylan surprised fans by appearing in a commercial for Victoria’s Secret. While he had previously licensed his music to advertisers, this was Dylan’s first time actually being in a commercial. The ad cuts between Dylan and model Adriana Lima in a lavish home. 

“We had done some spots last year with Dylan’s music, and they got a great response,” creative director, Ed Razek, said, per EW. “So Les [Wexner, Victoria’s Secret’s CEO] asked, ‘Do you think Dylan would do a commercial?’ It was a stunningly bold idea. We called his management, they found a two-day hole in his schedule, and off we went to Venice.”

Bobo Dylan wears a hat and sits at a piano.
Bob Dylan | Dave J Hogan/Getty Images for ABA

While Dylan’s record label thought the ad was a good opportunity to introduce his music to a new generation, Dylan didn’t speak about his reasoning.

“I can’t speak for his motivation, but it certainly wouldn’t be commercial,” Razek said.

2. Bob Dylan sang in a commercial for Apple

In 2006, Dylan appeared in an Apple ad to promote the iPod. In it, he appears, playing the guitar and singing in near-silhouette alongside a dancer. Through his deal with the company, his new album, Modern Times, and an exclusive box-set collection became available on iTunes. 

“Bob Dylan is one of the most respected poets and musicians of our time, and he is a personal hero of mine,” Steve Jobs said, per Campaign magazine. “Being able to offer his new album and the exclusive box set of his works on iTunes is a real thrill for us.”

Dylan’s promotion of the iPod was a bit surprising, as he has said that his favorite way of listening to music is on antique record players.

3. He appeared in archival footage for Pepsi

In 2009, Dylan and the Black Eyed Peas’ will.i.am appeared together in a Super Bowl commercial for Pepsi. The ad featured an updated version of Dylan’s song “Forever Young,” playing over both old and modern clips. 

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Dylan barely had to lift a finger for this ad. While it does feature shots of him, they are all decades old. He was in a Super Bowl commercial without ever having to show up on set. 

4. Bob Dylan faced accusations of being a sell-out after a Chrysler commercial

Dylan raised eyebrows again when he appeared in another Super Bowl commercial, this time for Chrysler. This was not even his first car commercial — in 2007, he drove a Cadillac Escalade in an ad — but it shocked fans all the same. 

In the ad, Dylan urged viewers to buy the American-made vehicle. That same Super Bowl, Dylan’s song “I Want You” appeared in an advertisement for Chobani yogurt. Perhaps because there were two more Dylan ads than expected, fans took to social media and called the musician a sell-out. At this point, he had already appeared in a number of ads, proving that no matter how many times Dylan sells out, it will always feel like a shock.