Bob Dylan's Whiskey & 6 Other Times He Entered the Marketplace

Bob Dylan
Christopher Polk/Getty Images for VH1

Bob Dylan onstage during the 17th Annual Critics' Choice Movie Awards held at The Hollywood Palladium on Jan. 12, 2012 in Los Angeles.

When it comes to finding another side of Bob Dylan, no decade comes close to the 2010s. Even his legendary stint as a “voice of a generation” of the ‘60s comes off as rather quaint in comparison to Dylan, age 75, who alternatively presents himself to the public as a Sinatra-style crooner, an iron sculptor and a Nobel-winning lecturer on Homer, Swift and Remarque. Now, Dylan’s revealed his newest side-venture: Heaven’s Door, a Dylan-branded whiskey company.

Heaven's Door's initial rollout includes a straight rye, straight bourbon and a double-barreled whiskey. In a statement to The New York Times, Dylan expressed his intentions behind the project: “We both wanted to create a collection of American whiskeys that, in their own way, tell a story. I’ve been traveling for decades, and I’ve been able to try some of the best spirits that the world of whiskey has to offer. This is great whiskey.” And according to that piece, the making of the liquor had its own share of classic Dylan moments, like when he rejected a tasting because the flavor profile was missing something: "It should feel like being in a wood structure.”

Given the “grizzled crooner” image Dylan has cultivated over the past decade -- the promotional photos for Heaven’s Door show him tuxedo-clad in the wee small hours -- it isn’t super-surprising that the songwriter would have the urge to release some bourbon. But it’s just the latest example of Dylan’s dabbling in the commercial marketplace. This is in marked contrast to other prestige artists like Tom Waits, who successfully sued Frito-Lay in 1988 over hiring a Waits soundalike to hawk Doritos. Waits later described putting his music in any ad as “having a cow’s udder sewn to my face.”

Yet, Dylan has seemed to jump at the idea of using his image or likeness to sling yogurt, lingerie or SUVs. In honor of the debut of Heaven’s Door whiskey, here are six other examples of Dylan’s weird ventures into the commercial sector.

2004: Dylan Leers Uncomfortably Through a Victoria’s Secret Ad

While he never had anything near the wit of his buddy John Lennon (or even Paul), Dylan relished in being cagey and smart-assed to the press in the mid-’60s, whether calling himself a “song-and-dance man” or joking he’d only sell out for “ladies’ undergarments.” You can’t deny Bob’s follow-through. To the strains of his grouchy, guttural “Love Sick,” Brazilian model Adriana Lima saunters around in lingerie and angel's wings while the camera pans to Dylan’s pencil-mustached mug. Shrouded in a digital blue, nobody looks entirely comfortable, but Dylan is all-in with the lothario bit. Hard-core Dylan fans weren’t too pleased, with John Baky, a curator of Dylan material at La Salle University, reacting poorly to the commercial: “I’m going to have to go blow my brains out.”

2006: “Someday Baby” Becomes a Cross-Promotional Push With Apple

The intertwining story of Bob Dylan and Apple is really worthy of its own article, given that the company’s founders, Steve Jobs and Steve Wozniak, initially bonded over their Dylan obsession. Later, Jobs even dated Dylan’s old flame, Joan Baez; when she ran into him years later and asked, “How does it feel to have changed the world?,” Jobs responded, “OK.” But we digress -- another earlier example of Dylan’s foray into the commercial realm was this appearance in an Apple ad, which was itself cross-promotional: Dylan was on the campaign trail for one of his better latter-day albums Modern Times.

2009: Raps Along With Vintage Dylan Footage to Hawk Pepsi

It’s one thing to sign on to a campaign to sell cola but another to volunteer your younger, more stylish self to do the dirty work and then get the guy from the Black Eyed Peas onboard too. This is the only piece of recorded music history that features the writers of “Visions of Johanna” and “My Humps,” with the latter rapping all over the Planet Waves cut “Forever Young.” The ensuing Super Bowl ad attempts to float the similarities between the two artists, mostly in that they both wear cool sunglasses. Doing it all for the Pepsi.

2014: Chrysler Gets the Dylan Bump: “Let America Build Your Cars”

Dylan has mused on advertising in his songs since at least 1963, when he mused in the song “I Shall Be Free”: “I flip the channel to number four/ Out of the shower comes a football man/ With a bottle of oil in his hand.” Still, it was especially jarring when he unapologetically appeared as a Chrysler spokesman in a Super Bowl XLVIII ad. No matter which way you slice it, hearing a songwriter who questioned nearly every element of “the system” spout jingoisms like “Is there anything more American… than America?” feels diametrically wrong.

2014: “I Want You” Takes On a New Message Involving Bears and Yogurt

The Chrysler ad wasn’t the only ad of 2014’s Super Bowl to flummox Dylan fans: A similarly Dylan-approved ad for Chobani Greek yogurt appeared during the same game. A cut from Blonde on Blonde, Dylan’s sprawling, poetic magnum opus in which he perfected his “thin, wild mercury sound,” “I Want You” went on to take on a rather different message involving a bear who is so obsessed with yogurt that he destroys a folksy general store. Genius! 

2015: Watson Cross-Analyzes Dylan’s Songs in an IBM Ad

Dylan may have been an early spark that fed Steve Jobs’ imagination, but when it came to selling computers, he didn’t have brand loyalty. In a 2015 ad for IBM, Watson claims he has listened to all of Dylan’s songs and has boiled them down to two themes. “I can read 800 million pages per second. My analysis shows your major themes are time passes and love fades,” Watson informs Dylan. “That sounds about right,” says Dylan coolly, not mentioning the real theme, one that applies to his entire life’s work and even his willingness to appear in any part of the commercial sector regardless of fan backlash: I do me, and me only.