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.