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The concept of a musician “selling out” has nearly all but evaporated over the last decade and a half. Reliable revenue streams generated by album sales used to allow for a solid middle class of independently-minded musicians are gone, replaced by insultingly low payouts from exploitative tech companies. Your favorite bands gotta get paid where they can, often doing so through constant, soul-crushing touring (hard), and ethically-challenging brand partnerships (easier?).

Most music fans now don’t think twice when they hear a track by a favorite up-and-coming artist in an ad, there’s even a sort of vicarious thrill to the situation, like, “oh nice, they probably got a decent chunk of money for this.” Like it or not, the 21st century has rendered selling out all but a necessity for many creative people. Back in 2004, a bizarre pairing of legendary boomer icon and problematic underwear monolith was a monumental paradigm shifter in a lot of ways. If Bob Dylan can sell out, why can’t we?

The Bob Dylan Victoria’s Secret ad premiered during an episode of American Idol in 2004. I wasn’t watching at the time, but I can imagine being very confused by lusty glances traded by the weird looking old dude and the winged model four decades his junior, soundtracked by a croaky ballad about regret. What is this? Who is this for? The whole thing seems engineered for the 46-year-old dads stuck in the living room watching Idol with the rest of the family: a REAL musician who plays REAL instruments hanging out with a smokin’ hot babe in a sick old mansion.

According to an Entertainment Weekly article written a week after the commercial’s premiere, the idea came straight from the top: Victoria Secret CEO and longtime Jeffrey Epstein associate Les Wexner heard from their ad firm that Dylan had recently started allowing commercials to use his music, and wondered if the man himself would be open to appearing in one of their famously steamy spots. Dylan agreed, and the rest is history.

Oddly enough, Bob may be staying true to his younger, outspokenly anti-establishment self here. He left himself an out way back in 1965, when during an interview, he joked (?) that he’d consider selling out to one commercial interest: “ladies’ garments.” Stay tuned after the clip for an extended version of the ad, with even more male gaze!

One last note here, a quick detour related to “Love Sick,” the track that plays over the ad. A single from his acclaimed 1997 album Time Out of Mind, “Love Sick” is tied to another ridiculous cultural moment that you should absolutely remember exists: the Soy Bomb incident at the 1998 Grammys. About two and half minutes into a live performance of “Love Sick,” an uninvited shirtless man danced frantically next to Dylan with the words “SOY BOMB” written on his chest. After almost a minute of enthusiastic thrashing and jerking, the intruder, later revealed to be performance artist Michael Portnoy, was pulled offstage.

The whole thing was perfectly weird, uncomfortable, and devoid of context, and we should all take a moment to appreciate Portnoy for actually achieving his Improv Everywhere-ass goal of injecting some whimsy and absurdity into an otherwise stuffy, mannered performance.