Whiskey Review: Heaven’s Door Bootleg Series Vol. III

, | April 23, 2022

Editor’s Note: This whiskey was provided to us as a review sample by Heaven’s Door Spirits. This in no way, per our editorial policies, influenced the final outcome of this review. It should also be noted that by clicking the buy link towards the bottom of this review our site receives a small referral payment which helps to support, but not influence, our editorial and other costs.

The collaboration between Nobel Laureate Dylan and Chicago firm Spirits Investment Partnership has its origins in the name of the “Bootleg” series. Industry veterans Marc Bushala (co-founder of Angels’ Share Brands and CEO of SIP) and Ryan Perry (former whiskey developer with Diageo, currently COO of SIP) first considered working with Dylan when they noticed a trademark for “Bootleg Whiskey” filed in his name. The use of the word “bootleg” in connection with Dylan has something of a poet’s touch, with two, related meanings commonly referring to surreptitiously produced spirits or audio recordings.

Notwithstanding an excellent track from Dylan’s Bootleg Tapes, Spirits Investment Partnership’s vision had more in common with a luxury product than moonshine. Bushala and Perry’s access to an extensive library of whiskeys offers a vast quantity of potential blends, and they set out to develop a range of expressions in conversation with the brand’s namesake and settled on the name “Heaven’s Door,” which recalls one of Dylan’s most recognizable songs.

They did not, however, dispose of the term “bootleg” entirely. In addition to their core expressions, Heaven’s Door produces a collectible bottle yearly as part of their Bootleg series. Trading more on the word’s connotations of elusiveness or exclusivity than illegality, the Bootleg offerings are limited releases of rare, otherwise unreleased expressions. The 2021 bottle is a 13-year-aged Kentucky Bourbon finished in casks of Andalusian vino de naranja, an aperitif made by macerating orange peels in white wine. 

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All bottles under the Heaven’s Door label showcase Bob Dylan’s visual artwork. The core expressions are adorned with his ironwork designs, and the ceramic bottles of each year’s release in the Bootleg series feature his paintings. Given that the brand is still young, Heaven’s Door’s whiskey is currently sourced, but plans are underway for Dylan to make a further contribution to the Nashville Skyline in the form of a distillery.

Heaven's Door Bootleg Series Vol. III review

Heaven’s Door Bootleg Vol. III (image via Heaven’s Door Spirits)

Tasting Notes: Heaven’s Door Bootleg Vol. III

Vital Stats: 13 year Kentucky Bourbon, finished in vino de naranja casks, 121.2 proof, priced at $545/750mL

Appearance: Pleasant copper coloring, holding a glass up to light accentuates a light, orange hue at the margins. Moderate viscosity, light legs with some staying power 

Nose: Equal parts sweet and spicy. Aromas of stone fruits and corn on the cob grilled-and-buttered are accompanied by a firm black pepper tingle. 

Palate: If I’d tasted this blind, I’d never have guessed it was over 100 proof. This drinks very pleasantly, what little burn there is on the palate is more of a continuation of the black pepper brightness from the nose. This comes right at the outset, hand in hand with classic cherry and oak notes. These give way to much more unique flavors, as a pronounced flavor of toasted, rustic rye bread with honey fades into custard and cream soda on the finish.



This is priced and packaged as a luxury product, it sips like one to boot. The flavors are mature and well-integrated, simultaneously unique and accessible. Few celebrity-associated brands merit a spot on the collectors’ shelf, but the third installment of Heaven’s Door’s Bootleg series deserves a space, both as a piece of Dylan memorabilia and as a high-end whiskey.

User Review
3.57 (7 votes)