Caribbean Wind: Bob Dylan's Latest Whiskey Is Finished In Jamaican Rum Casks

Painting on the bottle? Yep, Dylan did it.

So much of Bob Dylan’s story is shrouded in myth and half-truths and unknowns and plain old malarkey that it’s hard to know when to take him at face value. So when it’s said that Dylan participates actively in selecting the whiskeys to be bottled bearing his name and the Heaven’s Door imprint, do we take it with a grain (or several) of salt? And given that celebrity-branded booze is about as common as empty Fireball mini-bottles littering the sidewalk on weekend mornings, should we give Bob Dylan’s whiskey any more thought than, say, his large-scale wrought-iron sculptures? (Which are actually pretty cool, but I rarely think about them.)

In my case, I can’t help it because I’ve been a Dylan nut since I was about 15, and a drinker of whiskey from roughly the same age. I can’t, however, say that I’ve been an unequivocal fan of the Heaven’s Door’s range. I first tried them before the brand’s existence was even announced, when Bob or whoever was creating the blends was still in the tinkering stage. I thought the early iterations were awful and didn’t hesitate to say so. Did my opinions play any role in the rejiggering of the blends that wound up hitting the market in 2018? Probably not, but I’ll take some credit anyway.

I’ve generally been lukewarm on Heaven’s Door products. I’ve liked some more than others, and there was a 10 year old Tennessee bourbon (NOT a “sour mash whiskey”!) that I thought was very good, but the quality so far has been on a par with Street Legal more than Blood On The Tracks. Until now. The Bootleg Series, named after his ongoing musical from-the-vaults project, is a series of limited edition — and pricey — expressions that debuted last year with a 25 year old Canadian rye finished in Mizunara oak casks. Again, it was good, but the whiskey equivalent of Highway 61 Revisited it wasn’t. The Bootleg Series II: 2020 Edition (52.3% ABV, $500) is a 15-year-old bourbon (provenance not stated, so it could well be from the legendary MPG distillery in Indiana) finished for an undisclosed amount of time in barrels that formerly held Jamaican potstill rum, and then bottled at cask strength.

The first thing a lot of people think when they hear the word “rum” is sweet. But Jamaican potstill rum is not your typical rum — it can be earthy, funky, even vegetal. So I dove into this one not quite sure what I was going to get — would it be an easygoing, Nashville Skyline-type sipper? An experimental dud like Empire Burlesque? Well, turns out it’s a lot like Rough And Rowdy Ways, the album Dylan put out earlier this year. Like the album, the whiskey definitely won’t be for everyone. If you’re looking for a classic aged bourbon, look elsewhere, but if you’re looking to challenge your palate, look no further. Rather than imparting sweet molasses notes, that funky Jamaican rum influence lends a savory, almost meaty flavor to the proceedings, with a lovely, dry and mellow finish. Despite the relatively high proof, water is not necessary or recommended here. It’s not like any bourbon I remember trying — I found myself going back to it repeatedly, surprised anew every time, the same way I became addicted to “Murder Most Foul,” the 16 minute-plus epic from Rough And Rowdy Ways that bizarrely became Dylan’s first-ever #1 single.

Is it worth $500? Well, when you consider the gorgeous box and the bottle that features a painting by Bob himself, if you’ve got the cash it’d make a great gift for the Boomers and middle-aged classic rock fans in your life. And you don’t have to love Dylan to love this whiskey, although it doesn’t hurt. I’m just hoping he really did help pick this one. It’s weird but spectacular… kind of like the man himself.