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Celebrity bourbon, like celebrity tequila or anything else “celebrity”, is an odd beast. White labeling is a very real thing — that’s where big-name celebrities slap their names on a label, spend some time promoting the bottles, and then collect checks with little to no real influence on the process. But that’s not always how celebrity-driven bourbons come to be. Some famous folk actually dig into the process of making whiskey, help pick barrels and make blends, and spend a large amount of time championing the whiskeys they helped make.

Today, we have a bit of a mix of both worlds. Some of these bottles are sourced whiskeys that were released in an effort for a celebrity to jump on the bourbon boom. Some of them are passion projects. But does that love for the game shine through in what’s actually in the bottle? Or can an indifferent star make a better bourbon with a great brand backing them?

We’ll see!

Today, I’m tasting five bottles blind and then ranking them on taste alone. I’ve kept this a little smaller purposefully. The main reason is that when I’m tasting ten or 12 (or more) drams at once, some simply get lost in the mix — a few rise to the top, a few sink to the bottom, and the middle can become sort of an extended tie. When there are fewer drams competing, the competition becomes fierce because there’s nowhere for a middling dram to hide.

Our lineup today is:

• Drake’s Virginia Black Decadent American Whiskey
• Bob Dylan’s Heaven’s Door Redbreast Edition
• Matthew McConaughey’s Longbranch
• Scottie Pippen’s DIGITS Bourbon
• Terry Bradshaw’s Bradshaw Bourbon

I was lucky enough to score a few of these from a bar owner and whiskey collector down in Prague where I host whiskey tastings to help keep things new and varied (hence the small taster bottles in some of the images). Let’s get to it!

Part 1: The Tasting

Taste 1

Tasting Notes:

This is thin from the nose to the end. There’s a touch of vanilla extract with a plastic vibe on the nose that leads towards a hint of old lemon peel. The taste is pretty watery with a touch of caramel and a mild spice that leans towards cinnamon toast. The finish arrives pretty quick with a little note of oakiness.

This feels like “bourbon” but only just.

Taste 2

Tasting Notes:

The nose draws you in with a worn leatheriness next to dark stone fruits, brittle toffees, and something that feels like apricot jam with a good dose of winter spices. The palate is nutty (ranging from nutshell to marzipan) with a sticky toffee pudding vibe that leads towards plum candies. That sweetness gets very creamy with a vanilla pudding base as a light sense of stringy cedar barks leads back to that sweet plum candy.

Taste 3

Tasting Notes:

There are very light notes of citrus on the nose that feel like a distant lemon-lime with a wet wood vibe. The taste dried that wood out immediately, driving it towards almost pine wall paneling with hints of dry and dark spices, peach pits, and vanilla that all leads to this beautiful caramel candy end.

Taste 4

Tasting Notes:

This opens with a sense of vanilla extract that leads towards slightly singed popcorn with a touch of butter and an echo of cherry soda. The palate is classic bourbon with notes of caramel sauce, dark spice, light oak, and vanilla dancing with slight hints of leather and cherry tobacco. The end holds onto the vanilla before going full cherry candy on the finish.

Taste 5

Tasting Notes:

This is a wild nose that goes from Wether’s Originals to leather-bound books to drug store aftershave. The palate is all about soft spices with a woody vibe that’s a little bit wicker and a little bit oak. The finish holds onto the spice and warms up considerably before veering headfirst into apple candy sweetness.

Part 2: The Ranking

5. Virginia Black Whiskey — Taste 1

ABV: 40%

Average Price: $40

The Whiskey:

This whiskey is a collaboration between tequila maker Brent Hocking of DeLeón Tequila and Drake. The juice is a blend of high-rye bourbons from MGP that aged for two, three, and four years. That blend is then proofed all the way down to 40 percent before it’s bottled in what best can be described as a fancy art-deco perfume bottle.

Bottom Line:

This was last and it wasn’t even close. The 40 percent ABV meant that water kind of took over the whole flavor profile and left a faint hint of what whiskey might have been in those barrels.

This was just … so disappointing.

4. DIGITS Bourbon — Taste 4

ABV: 46%

Average Price: $70

The Whiskey:

This bottle is a collaboration between Bulls superstar Scottie Pippen and Napa wine superstar Dave Phinney. The juice is a sourced five-year-old whiskey that’s distilled in Tennessee, likely in a place that rhymes with “Tacoma”, alongside some MGP whiskey from Indiana. The barrels are sent to Mare Island, off San Francisco, where they continue aging before vatting, proofing, and bottling.

Bottom Line:

This is miles ahead of the bottle above. There’s a real sense of a well-built whiskey here that weirdly starts off a little thin but builds towards a very solid finish. I could see using this in cocktails very easily but I don’t know if it’s quite a sipper, like its price point suggests.

3. Wild Turkey Longbranch — Taste 3

ABV: 43%

Average Price: $40

The Whiskey:

A few years back, Wild Turkey brought on Matthew McConaughey to be the brand’s Creative Director and design his own whiskey. The product of that partnership was launched in 2018. The juice is a wholly unique whiskey for Wild Turkey, thanks to the Texas Mesquite charcoal filtration the hot juice goes through. The bourbon then goes into oak for eight long years before it’s proofed and bottled.

Bottom Line:

I think this could have won that day had the first half (the nose and the opening of the palate) had been bolder. This dram ends amazingly but you have to sort of force yourself to get there. Still, it’s pretty solid once you’re past the first act.

2. Bradshaw Bourbon — Taste 5

ABV: 51.9%

Average Price: $52

The Whiskey:

Bradshaw Bourbon is made by Green River Distilling Company in Owensboro, Kentucky. The bourbon (and now a rye) is a collab between former Super Bowl champ Terry Bradshaw and Silver Screen Bottling Company, which acts as a sort of bottling fixer between a celebrity and a distiller or barrel house. The juice is a two-year-old bourbon made with 70 percent corn, 21 percent rye, and nine percent malted barley. It’s proofed to a hefty 103.8.

Bottom Line:

This really stood out. That aftershave moment of the nose threw me a bit (it’s not too out of leftfield) but made total sense with the whole experience. Then the palate truly popped as a very classic Kentucky bourbon. There weren’t any big bells or whistles but there didn’t need to be. This felt like a really solid “table bourbon” that you could sip on the rocks or throw in a cocktail and all will be well.

1. Heaven’s Door Redbreast Edition — Taste 2

ABV: 50%

Average Price: $115 ($99 MSRP)

The Whiskey:

This whiskey is a collaboration between Heaven’s Door Master Blender Ryan Perry and Redbreast’s legendary Master Blender Billy Leighton. The duo worked long and hard to create multiple whiskey expressions, which Bob Dylan taste-tested and granted final approval on. The juice in the bottle is Heaven Door’s low-rye 10-year-old Tennessee bourbon. They take that whiskey and fill it into Redbreast whiskey casks that had previously aged Irish whiskey for 12 years. After 15 months of final maturation, those barrels are vatted and slightly proofed down with soft Tennessee spring water.

Bottom Line:

Nothing came close to this. It’s complex, accessible, pronounced, nuanced. There’s a real depth that makes sense and welcomes you in. This is the winner by a country mile. I wanted to immediately go back. Given that Dylan actually helps select barrels and works with the blending, I have to think that he’s got one hell of a whiskey palate.

Part 3: Final Thoughts

I think I would have been shocked if Heaven’s Door didn’t win. The majority of their lineup is pretty damn fine whiskey across the board. Still, when I saw that Bradshaw Bourbon was my second-place pick, I was shocked. I had written that bottle off as “Terry probably just slapped his name on a bottle.” That’s not exactly true, he is part of the process, in theory. He’s out there pounding the pavement for the brand and has a long history of barrel picks going back a long way. It shows in this whiskey as it feels like it was made by someone who adores bourbon.

For me, the Longbranch was the splitting point. That whiskey finished so beautifully that it felt like a real shift from “shitty” to “okay” to “very nice” in this lineup. Still, I wanted a bit more up top and up just wasn’t there.

When it comes to Scottie Pippen’s bourbon, my best summation is this “yup, that’s bourbon alright.” It just left me a bit cold while tasting it and now while thinking about it. I can’t really see myself ever going back to it.

Finally, there’s Drake. Sorry, but cool perfume bottle aside, this was “meh” at best and “try again, folks” at worst. The 80 proof just let too much water take everything over and there was very little left.

I guess that means Bob Dylan remains the GOAT, in more ways than one.