By Ben Sisario

April 28, 2018

In late 2015, an unexpected name popped up in the liquor industry press: Bob Dylan.

A trademark application for the term “bootleg whiskey” had been filed under Mr. Dylan’s name. Among those who noticed the news was Marc Bushala, 52, a lifelong fan and a liquor entrepreneur whose bourbon brand, Angel’s Envy, had just been sold for $150 million. Mr. Bushala said he immediately spent weeks “obsessing over this concept of what a Dylan whiskey could be.”

So he reached out, and after being vetted by Mr. Dylan’s representatives, Mr. Bushala — who speaks branding jargon like “flavor profile” and “name exploration” in an earnest Midwestern accent — talked to Mr. Dylan by phone, and proposed working together on a portfolio of small-batch whiskeys. As he saw it, there was just one problem: The name “bootleg,” while an apt Dylanological pun, wasn’t quite right for a top-shelf liquor. Might Mr. Dylan, Nobel laureate, be open to some name exploration?

“It was a little bit daunting,” Mr. Bushala said of his pitch.

But it worked. Next month, he and Mr. Dylan will introduce Heaven’s Door, a collection of three whiskeys — a straight rye, a straight bourbon and a “double-barreled” whiskey. They are Mr. Dylan’s entry into the booming celebrity-branded spirits market, the latest career twist for an artist who has spent five decades confounding expectations.

Mr. Dylan is not simply licensing his name. He is a full partner in the business, Heaven’s Door Spirits, which Mr. Bushala said had raised $35 million from investors.

“We both wanted to create a collection of American whiskeys that, in their own way, tell a story,” Mr. Dylan said in a statement to The New York Times. “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.”

The marketing of celebrity alcohol tends to lean on the perceived lifestyle of its mascots. Drink George Clooney’s Casamigos tequila, for example — sold last year to the beverage giant Diageo for up to $1 billion — and acquire some of his movie-star glamour. Want to party like Jay-Z? Buy an $850 Armand de Brignac.

“It’s about fairy dust,” said Michael Stone, the chairman of the brand licensing agency Beanstalk, who is not involved with Heaven’s Door. “People are looking for some of the fairy dust to be sprinkled on them from that celebrity’s lifestyle.”

Heaven’s Door is meant to conjure a broader idea of Mr. Dylan that is part Renaissance man, part nighthawk. The label design is derived from his ironwork sculptures, with rural iconography — crows, wagon wheels — in silhouette. And in promotional photos lighted like classic movie stills, a tuxedo-clad Mr. Dylan, 76, gazes off in a dark cocktail lounge or lonely diner, glass in hand.

Like his recent albums of standards, they portray Mr. Dylan as an urbane but still gritty crooner — one who might well wind down his day with a glass of bourbon.

“Dylan has these qualities that actually work well for a whiskey,” Mr. Bushala said. “He has great authenticity. He is a quintessential American. He does things the way he wants to do them. I think these are good attributes for a super-premium whiskey as well.”

Mr. Dylan is entering the craft whiskey market as the business is exploding. Helped by a craze for classic cocktails, sales of American whiskey grew 52 percent over the last five years, to $3.4 billion in 2017, according to data from the Distilled Spirits Council.

But for those who have been listening closely, whiskey has been a decades-long thread throughout Mr. Dylan’s music, going back to the early outtake “Moonshiner” in 1963 and to Mr. Dylan’s version of the song “Copper Kettle (The Pale Moonlight),” on the 1970 album “Self Portrait,” which describes the distilling process in detail. (“Get you a copper kettle, get you a copper coil/Fill it with new made corn mash and never more you’ll toil.”)

Mr. Bushala said that over four or five meetings — always at Mr. Dylan’s metalworking studio in Los Angeles — and a number of phone calls, he had learned that his partner has a sophisticated whiskey palate.

Yet communication was still a challenge. Mr. Bushala and Ryan Perry, the chief operating officer, struggled to interpret Mr. Dylan’s wishes. Often they came in the form of enigmatic comments or simply glances.

“Sometimes you just get a long look,” Mr. Bushala said with a laugh, “and you’re not sure if that’s disgust or approval.”

He and Mr. Perry recalled Mr. Dylan’s tasting a sample of the double-barreled whiskey and saying that something was missing. “It should feel like being in a wood structure,” he said.

They struggled to decode the remark. What kind of wooden structure? A church? A railroad car? A barn? That led Mr. Bushala and Mr. Perry first to probing discussions about the nose — the liquor’s aroma in the glass — and then to experiments in how they toasted the barrels in which the whiskey is aged.

Months later, the men returned with a sample that they felt embodied “that sweet, musty smell of a barn,” Mr. Bushala said, and presented it to Mr. Dylan, who commented approvingly.

His oblique feedback, Mr. Perry said, “really helped us think about barrel finishing in a different way.”

The first batches of Heaven’s Door were developed with Jordan Via, formerly of the Breckenridge Distillery in Colorado. Together, the team tried various novel finishes. The rye, for example, was aged in cigar-shaped oak barrels made from wood harvested in the Vosges region of France.

To preserve Mr. Dylan’s original name for the whiskey, the company will issue an annual Bootleg Series in limited editions, in ceramic bottles decorated with his oil and watercolor paintings. The first, a 25-year-old whiskey, will be released next year and cost about $300. (Heaven’s Door’s standard line goes for $50 to $80 a bottle.)

The idea of Mr. Dylan’s being connected to a commercial venture always activates some level of outrage, as it did in 2014 when fans cried “sellout”for his involvement in two Super Bowl TV ads: one for Chobani yogurt, which used his song “I Want You,” and another for Chrysler, in which Mr. Dylan recited a patriotic script about the car industry.

But Mr. Dylan has never shied from commercial deals, and in the long run they have barely grazed his reputation. In 1994, he allowed Richie Havens to sing his anthem “The Times They Are A-Changin’” in an ad for the button-down accounting firm Coopers & Lybrand. Ten years later, Mr. Dylan was mocked for appearing in a Victoria’s Secret commercial (in which he tossed his black cowboy hat to a supermodel wearing angel wings). Since then, he has done spots for Apple, Cadillac, Pepsi, IBM and Google.

Mr. Dylan has also made a novel licensing deal for his full song catalog to be available for use in a television drama now under development.

Bill Flanagan, a veteran music journalist who has interviewed Mr. Dylan, likens him to Hank Williams and Johnny Cash — self-made entertainers who saw no conflict in joining the marketplace.

And then there is simply Mr. Dylan’s talent for provocation.

“Dylan has always resisted any attempt to fence him in,” Mr. Flanagan said. “As soon as people start calling him king of the folkies, or patron saint of the counterculture, or beloved anticommercial leftist icon — he almost always does something to thwart that.”

Whether Heaven’s Door can compete is another question. Mr. Bushala was one of the founders of Angel’s Envy, which was introduced in 2011 and sold to Bacardi four years later after developing a reputation for quality and innovation. Yet the whiskey aisle keeps getting more crowded. According to Nielsen, more than 20,000 kinds of spirits are sold in the United States, and last year there were 27 percent more whiskeys on sale than in 2013.

Mr. Bushala said that in their first conversation, he had told Mr. Dylan that “whiskey drinkers are a very cynical crowd” and that the success of their enterprise would depend on the quality of the product, not Mr. Dylan’s image.

Yet a few months after their first meeting, Mr. Bushala said, he had a scare when Mr. Dylan was announced as the winner of the Nobel Prize in Literature — and then waited weeks to acknowledge the honor, leading to speculation that he might not accept. “Oh, no, a P.R. nightmare!” Mr. Bushala remembered thinking.

But then he realized that defying expectations was “very much on brand” for Mr. Dylan, and likened the Nobel episode — ultimately, a success — to their whiskey deal.

“For people who are surprised that he did a whiskey,” Mr. Bushala said, “I guess they don’t really know Dylan. People who know him expect him to do things they would never expect.”

This article originally appeared in The New York Times https://nyti.ms/2rlJaQF