Our New Whiskey Critic Breaks Down His Favorite Sips Of Bourbon Ever

It feels good to be the new kid on the block. Mainly because everyone has their eye out and wants to know what you’re all about. What makes you you?

Well, I’m ready to answer that question by laying out my 10 favorite sips of bourbon ever. It’s a big ask, but I’m up to the task.

For a bit of background, I’ve been enjoying bourbon for well over 10 years and doing so professionally for the past four. Over that time… let’s just say I’ve had a lot of bourbon. Whether it was straight from the barrel at Buffalo Trace Distillery, in the gallery for Sotheby’s first exclusive American whiskey auction, or on the edge of the Grand Canyon with Uproxx’s previous whiskey critic, Zach Johnston, I’ve been on a coast-to-coast quest to determine the best.

Fair warning, you may have to search high and low for a mere sip of some of these bottles. Rarity may not be a prerequisite for excellent bourbon but when we’re talking about whiskey as good as the ones listed below, well, they certainly tend to be hard to find. Hell, one of them was famously christened “the best bourbon you’ll never taste.” But this whiskey critic has tasted them all more than once, and I assure you the risk (to your wallet) is worth the reward.

Here’s my list of 10 bourbons that I think are simply the best.

10. 2017 Al Young 50th Anniversary Limited Edition Small Batch

Al Young 50th Anniversary Bottle
Four Roses Distillery

ABV: 53.8%

Average Price: $1,300

The Whiskey:

The late Al Young is one of the most famed names ever tied to the Four Roses brand. The Kentucky Distillers’ Association Hall of Famer was honored with his own limited edition expression for his 50th anniversary with the brand in 2017. Among Four Roses connoisseurs it’s considered some of the best whiskey they’ve ever bottled.

Limited to just 10,000 bottles, it’s also one of those special releases that send the secondary market into a frenzy as fans try desperately to purchase the dwindling number of unopened bottles.

Tasting Notes:

Nose: The aromas of honeysuckle and fruit parfait are accented by a sprinkle of cinnamon and sweet leather, which is the primary indication that there is some older bourbon in this blend.

Palate: The liquid is immediately lush with bright fruits, think of apricots and pears, along with some vanilla bean ice cream and a gentle backbone of oak and mellow spices.

Finish: The honeysuckle and fruity notes linger on the back end of every sip and they’re joined by a healthy dose of allspice making for a long-lasting, albeit mellow, finish reminiscent of caramel-drizzled fried apple pie.

Bottom Line:

After trying Al Young 50th Anniversary Limited Edition Small Batch on several occasions (and being one of the lucky few to own a bottle) it remains my standard bearer for how excellent Four Roses bourbon can be. The ABV isn’t overwhelming but it delivers flavor in spades which is proof positive that bourbon doesn’t need to be big and bold to remain full of flavor.

9. King of Kentucky

King Of Kentucky

ABV: It varies by release.

Average Price: $2,500

The Whiskey:

Since 2018 King of Kentucky has been an annual release from the folks at Brown-Forman that showcases the very best of their well-aged stock. Because each of these expressions are bottled as single barrels you can expect slight variations between them, but versions in the 14-15 year age range are truly the best of the bunch. While the contemporary expression is a highly sought-after bourbon, it was created to honor a fairly quotidian blended whiskey of the same name which was originally produced way back in 1881.

Tasting Notes:

Nose: Cinnamon bark and figs are evident but rich leather and juicy black cherry notes are the stars of the show here.

Palate: A big wallop of polished leather and barrel char envelopes the tongue before tart cherries, fig, and dark chocolate find their footing. This is a pour that comes across as complex and dense from the first sip and forces you to lean forward and appreciate every rich layer. Gooey caramel, coconut rice pudding, and pops of Aleppo pepper flakes aren’t uncommon either.

Finish: Can you say, long-lasting? Sure, but you won’t want to speak as you savor just how decadently sweet this finish is while it hangs around well after your final sip.

Bottom Line:

What makes King of Kentucky reign supreme is the unapologetic boldness of its performance on the palate coupled with an intoxicating bouquet of aromas on the nose. It simply captures all there is to love about high-proof, full-bodied bourbon of a certain age. It’s no cliche to say these bottles are fit for a king.

8. Eagle Rare 25

Eagle Rare 25
Buffalo Trace Distillery

ABV: 50.5%

Average Price: $10,000

The Whiskey:

Eagle Rare 25, which was first released by Buffalo Trace Distillery in 2023, represents the pinnacle of their celebrated Eagle Rare Bourbon lineup. To create this whiskey they took barrels that were initially earmarked for their Double Eagle Very Rare expression and began aging them in the experimental Warehouse X for an additional 5 years beginning in 2018.

Tasting Notes:

Nose: Cocktail cherries, gooey caramel, and freshly cracked black pepper greet the nose along with a robust yet refined aroma of oak which serves as an indication that this is well-aged whiskey.

Palate: Resplendent with mixed-berry tarts – raspberries and blueberries chief among them – you can also expect to find brown butter, candied ginger, and a surprisingly restrained sweet oak presence undergirding the entire affair.

Finish: While it isn’t the lengthiest finish of all time, those mellow spice notes fuse well with the brown butter and fruit-forward character of its flavors which allows each sip to gently recede from the palate.

Bottom Line:

What makes Eagle Rare 25 so exceptional is the innovative aging technique that Buffalo Trace Distillery uses to decelerate the impact of bitter and tannic notes while reaping the benefits of more favorable flavors that can only be achieved through maturity. The result is a stunning whiskey on its own merits that is even more remarkable for the fact it retains an impressive vibrancy in its old age.

7. Rare Character Obliteration

Rare Character Obliteration
Rare Character

ABV: 71.9%

Average Price: $600

The Whiskey:

It’s been a joy to witness (and taste) the incredible whiskey that Rare Character has been releasing since they were founded in 2021. The first of several show-stoppers for the brand might go down as their best bourbon ever – Obliteration. Limited to just 36 bottles, this 14-year hazmat bourbon of undisclosed origin disappeared in a puff of smoke when it was initially released online. Since then the spark of interest has grown into a roaring flame of approval as the folks who were bold enough to open those bottles tasted what was inside.

Tasting Notes:

Nose: Be forewarned, when nosing this whiskey you will face the fire as a rush of ethanol greets you at first. However, once you get acclimated to the ABV you’ll find peanut brittle, decadent dark chocolate, and savory cooked dates wafting out of the glass for your approval.

Palate: Again, the high heat of this bourbon will sting at first but once your palate is properly adjusted there are gobs of sticky caramel, syrupy black cherry, tobacco leaf, and freshly oiled leather like you might get on the tip of your tongue during the first game of spring training.

Finish: This is as long as a finish as you can expect from a bourbon. Enjoy it as baking spice detonates and those little flavor particles crash into chunks of fruity sweetness that cause a chain reaction you can still taste 20 minutes later.

Bottom Line:

While certain bourbons excel with finesse, Rare Character Obliteration barrels over your tongue leaving no prisoners behind. You can expect your palate to be on the receiving end of a dense and complex pour, capable of astounding and obliterating your taste buds in equal measure.

6. Very Old St. Nick 15 Year Red Wax

Very Olde St. Nick 15 Year
The Dusty Bunker

ABV: 57.4%

Average Price: $6,000

The Whiskey:

What’s the most famed name in bourbon history? Pappy Van Winkle? No, the other most famed name – Stitzel-Weller. That fame was birthed by the incredible whiskey that Julian Van Winkle was bottling for his Pappy lineup but he wasn’t the only one to find a home for such legendary liquid. Enter Marci Palatella who created the Very Olde St. Nick brand specifically for the export market in the late 1980’s. This particular 114.8 proof, 15-year version is believed to have been bottled between 1988 and 1991 by Julian Van Winkle III himself which adds a level of intrigue.

Tasting Notes:

Nose: The aromas immediately take a sweet approach with dried cranberries and toffee filling the air before warm vanilla and toasted oak begin to blossom. Think of the scent of campfire roasted marshmallows that have just turned light brown and slap that between two layers of graham cracker.

Palate: The oily viscosity is immediately striking but what follows is a rush of lush and refined flavors with cocktail cherries, bourbon balls, butterscotch, and boozy vanilla melding well with the gentle influence of clove and walnuts.

Finish: The finish clings to your palate and picks up a bit of maple syrup, black pepper, and a flaky croissant note that really ups the ante providing a notable butteriness to each sip that helps to hold the disparate parts together.

Bottom Line:

Dusty bourbons are often heralded for exhibiting a level of richness that isn’t matched by today’s offerings. Simply put, old Stitzel-Weller bourbon is the finest example of this. Look for the bright cherry and butterscotch notes to be particularly unique when compared to contemporary expressions then settle in for the decadent finish – another hallmark of what the best vintage bourbons can offer.

5. A.H. Hirsch 16 Year “Gold Foil”

A.H. Hirsch 16 Year Gold Foil
Preiss Imports

ABV: 45.8%

Average Price: $5,300

The Whiskey:

First dubbed “the best bourbon you’ll never taste” by a writer back in 2012, the legend of A.H. Hirsch’s 16-year “Gold Foil” has only grown since then. Initially distilled at Pennco Distillery, the man who ordered the whiskey – namesake Adolph H. Hirsch – never actually bottled it. That task fell to Julian Van Winkle III who did so with this 16-year-old bourbon at the behest of liquor store owner Gordon Hue in 2003. While there are several legendary releases of A.H. Hirsch bourbon floating around, the 16-year gold foil version featured the widest release (2,500 cases) and so inspired the popularity of the brand plus an entire book espousing its elusiveness and superlative quality.

Tasting Notes:

Nose: The effusive aromas of salted caramel, golden raisins, and a healthy sprinkle of nutmeg all show well here. Given some time there’s a bit of well-aged oak that develops in lockstep with a note of vanilla custard.

Palate: The density of flavors on the palate is immediately impressive considering its relatively mild proof. The tip of the tongue is where the taste of custard and golden raisins take hold, allowing salted caramel, a touch of sweet oak, and several dashes of nutmeg to accentuate every viscous sip.

Finish: Balance is the name of the game here, as each taste foregoes a drawn-out experience for a medium-length finish that encourages return trips to the glass (and the bottle) as you appreciate its simple sophistication.

Bottom Line:

A far cry from the punch-’em-in-the-face bourbons of today, A.H. Hirsch 16 Year opts instead to display the efficiency of a well-oiled machine. With a sumptuous flavor profile that instantly stuns and a bouquet of aromas that showcases beautiful balance, this is a bourbon that best exhibits the mantra “less is more.” Good luck finding it at its original suggested retail price of $45, though.

4. Michter’s 20 Year Kentucky Straight Bourbon

Michter's 20 Bourbon

ABV: 57.1%

Average Price: $6,000

The Whiskey:

The present-day Michter’s Distillery is led by President Joe Magliocco who, from day one, has employed some of the most knowledgeable folks in the industry with a single aim in mind – to create the best American whiskey possible. When it comes to America’s native spirit, the brand’s most successful effort can surely be considered Michter’s 20-Year Kentucky Straight Bourbon.

Tasting Notes:

Nose: Oh, yeah…this is mature bourbon. It plays all of the classics – black cherry sweetness, deep leather aromas, and refined oak – and does little to stray from them.

Palate: Again, Michter’s 20 is a straightforward sipper with black cherries, leather, and well-aged oak taking the reign and refusing to let go. Along the periphery, there are clove and black pepper aspects to be found in the spice department and sweet bits of butterscotch and vanilla extract to enhance the sweetness.

Finish: The lengthy finish is where those guest appearances recede and we’re back showcasing the three main flavors which impress due to their ample richness.

Bottom Line:

Featuring a blend of sourced bourbon that is painstakingly mingled and undergoes a proprietary filtration process, Michter’s 20 might just be the quintessential bourbon. Full of rich oak, mature leather, and black cherry, this is the whiskey above all others that demonstrates what well-aged bourbon should taste like.

3. Russell’s Reserve 1998

Russell's Reserve 1998
Rare Bird 101

ABV: 51.1%

Average Price: $1,400

The Whiskey:

Imagine, if you will, a time when Jimmy Russell isn’t playing a pivotal role in the Wild Turkey brand. It’s that very (harrowing) thought that inspired this limited edition which was comprised of 23 hand-selected barrels that Eddie Russell set aside in 1998. The idea was that they would eventually be bottled as a tribute to his dad Jimmy on the eve of his retirement. Well, 15 years later those barrels had reached the peak of their maturity but Jimmy wasn’t going anywhere. The barrels were dumped into steel tanks to preserve their flavor before being bottled and released in 2015. Despite its limited quantity and what was then an eyebrow-raising asking price of $250 the 2,070-bottle batch sold out quickly and is commonly cited as the very best bottle of Wild Turkey ever sold in America.

Tasting Notes:

Nose: Wild Turkey at its finest, which means a healthy helping of allspice and apple pie spices (with nutmeg and cinnamon leading the way) along with stewed red apples and an abundance of sticky caramel.

Palate: The red apples from the nose turn into more of a black cherry note here, developing a deeper sweetness that combines with the apple pie spices and adds some vanilla ice cream. The influence of oak sets a solid foundation for all of these flavors to reach their full potential as none of them manages to outshine the others, instead allowing them to crest in glorious harmony.

Finish: Here the oak influence grows and provides more of a platform for the baking spices to strut their stuff. The finish is satisfyingly lengthy which makes parsing each layer of flavor all the more enjoyable.

Bottom Line:

Not only is Russell’s Reserve 1998 a quintessential Wild Turkey bourbon, but it dials all of those prototypical flavors up to the umpteenth degree. Skewing delightfully on the dark end of the sweetness spectrum it contains a complexity that its single-barrel likeness hints at but never fully achieves.

2. Very Very Old Fitzgerald 12 Year

Very Very Old Fitzgerald 12 Year
The Whisky Exchange

ABV: 50%

Average Price: $7,000

The Whiskey:

We’ve talked a bit about Julian Van Winkle III but Old Fitzgerald was the flagship brand for his grandfather, Julian “Pappy” Van Winkle’s Stitzel-Weller Distillery. While the whiskey produced by Stitzel-Weller made its way into several other brand’s bottles over the years (many of them fetching tens of thousands of dollars on the auction market) there’s simply no topping the stuff they kept for themselves. In 1964 all bottles of Old Fitzgerald that were aged for at least 12 years received the “Very Very Old” designation, and for my money, they’re the best wheated bourbons ever to be produced.

Tasting Notes:

Nose: Candied walnuts, honey, and slightly musty oak make their way out of the glass at first. After a few waves of the hand, the aroma of honey only becomes more refined, and it is joined by a bit of orange peel, plenty of brown sugar, and a touch of leather to boot.

Palate: This is a spectacular bourbon from the first sip as candied walnuts and sweet oak fan out over the tongue and make way for pops of clove and nutmeg along the roof of the mouth. It’s oily and dense, allowing those flavors to take root on the palate and slowly grow over time.

Finish: Again, the finish benefits from its robust viscosity which holds all of the rich, sweet notes close and allows the earthy flavors of oak and leather to provide a superb balance on the back end.

Bottom Line:

With remarkable balance and considerable gusto, Very Very Old Fitzgerald 12-Year bourbon is a pure delight from start to finish. When it comes to wheated bourbons there are none finer as this Stitzel-Weller-produced bottle puts them all to shame. The Pappy Van Winkle of today is merely a shadow of what the man himself was producing, and that says it all right there.

1. Wild Turkey 14-Year Master Distiller Selection

Wild Turkey Master Distiller Selection
The Whisky Exchange

ABV: 53.5%

Average Price: $1,800

The Whiskey:

While Russell’s Reserve 1998 may hold the title of being the best Wild Turkey bourbon ever sold in America, Wild Turkey 14-Year Master Distiller Selection is the intercontinental champ. Reserved for the Japanese export market, bottled at 107 proof, and limited to roughly 6,000 bottles, Master Distiller Selection was said at the time to be, “Jimmy Russell’s vision of the ultimate bourbon.” With one sip I was immediately inclined to agree.

Tasting Notes:

Nose: Where Russell’s Reserve 1998 is more reminiscent of the dark sweetness Russel’s single barrels are known for, Master Distiller Selection is a masterclass of balance that allows the influence of oak, subtler baking spices like nutmeg and clove, and semi-sweet aromas like chocolate wafers and hazelnut to shine.

Palate: Dark chocolate and hazelnut gently wash away to reveal apple chips, butterscotch, and a faint touch of rosemary. Oak is evident but not overpowering which leaves enough room for those subtle spices from the nose to make themselves heard.

Finish: Absolute harmony between the subtle spice notes, semi-sweet flavors, and the earthy oak influence linger long after the last sip making for an awe-inspiring finish.

Bottom Line:

Come for the depth of flavor but stay for the way Wild Turkey 14 Year Master Distiller Selection remarkably balances everything that makes bourbon great. After I first tried this bourbon I tirelessly sought out a bottle of my own and paid a mint at an auction house to do so. While I rue the last-minute bidder who pushed the price of this bottle north of my ordinary bourbon budget, this is anything but ordinary bourbon. Wild Turkey 14-Year Master Distiller Selection is the best bourbon I have ever had the pleasure of sipping.