Remember When Bob Dylan Was in a Victoria’s Secret Commercial?

Throughout his 60-year career, Bob Dylan has regularly defied expectations. But in 2004, the last place fans expected to see the Voice of a Generation was in a lingerie commercial.

Not just his music, but the Bard himself, appeared alongside a winged supermodel in a television ad for Victoria’s Secret, a cameo that left viewers wondering whether Dylan had sold out or how he was supposed to help sell women’s underwear in the first place.

“We had done some spots last year with Dylan’s music, and they got a great response,” Victoria’s Secret creative director, Ed Razek, explained to the San Francisco Chronicle (via EW.com). “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.”

“We think this is a great way to reach people with Bob’s music,” Claire Mercuri, a spokesperson for Columbia Records, told the Chronicle in response to the ad. “We’re thrilled that he said ‘yes’ when we asked him to be in the commercial.”

In the commercial, Dylan’s moody ballad, “Love Sick,” from his 1997 album, Time Out of Mind, plays. Shots of a white wing-clad Victoria’s Secret Angel, model Adriana Lima, transition throughout, mingling with close-up shots of Dylan, squinting into the camera.

In the 30-second advert, no words are exchanged, just passing glances in an abandoned Venetian palazzo.

Watch the unusual exchange below.

Dylan’s album, Time Out of Mind, has just recently received the expanded bootleg treatment on Fragments—Time Out Of Mind (1996-1997): The Bootleg Series Vol. 17. The project became available on Jan. 27 this year.

Part of Dylan’s ongoing Bootleg Series, the expanded 5LP and 10CD deluxe edition includes an alternate version of “Love Sick,” recorded on January 14, 1997, at Criteria Studios. The collection also features unreleased recordings, like the songs “Dreamin’ of You,” “Red River Shore,” “Marchin’ To the City,” and “Mississippi,” along with other outtakes, demos, alternate versions, and live cuts.

Photo by Gus Stewart/Redferns via Getty Images