There’s something refreshing about being the fresh face in town. Especially when all eyes are on you, curious to unravel what sets you apart. What is your unique factor?

Well, I’m more than willing to shed some light on this mystery by sharing my top 10 dearest bourbon whiskeys of all time. It might be ambitious, but I’m ready for the challenge.

Just to set the stage, I’ve been a bourbon enthusiast for more than a decade and this has been my profession for the last four years. In this timeframe… let’s just say my bourbon encounters can’t be counted. My experiences range from tasting straight from the barrel at Buffalo Trace Distillery, witnessing the first exclusive American whiskey auction at Sotheby’s, to sipping on the edge of the Grand Canyon with Uproxx’s prior whiskey critic Zach Johnston. My journey has spanned the width and breadth of this nation, hunting for the most superior bourbon.

A word of caution, you might need to go to great lengths for a single taste of some of the gems on this list. While scarcity does not necessarily make a bourbon outstanding, when it comes to the whiskeys mentioned below, they are definitely elusive. For instance, one of them was notoriously dubbed “the best bourbon you’ll never sip.” Regardless, as a whiskey critic, I’ve been fortunate enough to taste each of them more than once, and I can vouch for the fact that the risk (to your pocket) is fully justified by the delight they offer.

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

ABV: 53.8%

Average Price: $1,300

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 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.

ABV: It varies by release.

Average Price: $2,500

Since its advent in 2018, King of Kentucky has marked an annual release from Brown-Forman that magnifies their finest well-aged stock. As these expressions are dispersed as single barrels, slight variations among them can be anticipated. However, those in the 14-15 year age bracket are truly the cream of the crop. This highly in-demand bourbon was forged to commemorate its fused whiskey predecessor of the same name originally crafted in 1881.

Tasting Notes:

Nose: The presence of cinnamon bark and figs is notable, yet the rich leather and luscious black cherry notes are the true spectacle.

Palate: A strong hit of well-tanned leather and barrel char wraps around the taste buds before the emergence of tart cherries, fig, and dark chocolate. This drink strikes as incredibly complex and rich from the very first taste, demanding your full attention to each flavorful layer. Notes of sticky caramel, coconut rice pudding, and bursts of Aleppo pepper flakes are also often present.

Finish: Is it enduring? Absolutely, but you’ll find yourself wanting to remain silent to thoroughly appreciate the lingering sweetness long after you’ve finished enjoying it.

Bottom Line:

The King of Kentucky stands proud with the unabashed potency of its palate presentation intertwined with a richly intoxicating aroma. It embodies everything there is to adore about robust, high-proof, matured bourbon. It’s not just an overused phrase to say such bottles are worthy of a king.

ABV: 50.5%

Average Price: $10,000

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 starting in 2018.

Tasting Notes:

Nose: The initial aroma presents cocktail cherries, caramel in its gooey form, and a strong offering of freshly cracked black pepper. The overwhelming but elegant scent of oak rounds out the sensory experience, signalling a well-aged whiskey.

Palate: Offering a grandiose mix of berries – with raspberries and blueberries taking the lead – the palate also teases you with brown butter and candied ginger. The sweet oak, which maintains a subdued presence, forms the base of the profile.

Finish: While the finish may not lay claim to being the lengthiest, it brilliantly integrates the mellow spice with brown butter and the fruity flavors. This allows each sip to gently fade away from the palate.

Bottom Line:

Eagle Rare 25 stands out due to the unique aging process implemented by Buffalo Trace Distillery. This method diminishes the influence of harsh and tannic notes while allowing the development of more pleasing flavors achievable only through maturity. The result is an outstanding whiskey with its own inherent merits, even more noteworthy for maintaining a significant brightness, despite its advanced years.

ABV: 71.9%

Average Price: $600

Rare Character has been producing exceptional whiskey since they began in 2021. Their initial series of releases introduced a probable top-performer of their bourbon range – Obliteration. Restricted to a mere 36 bottles, this 14-year-old hazmat bourbon of undisclosed origin was swiftly sold out upon its initial online release. The curiosity it stirred has since escalated into fervent approval by those brave enough to uncork and taste the contents of those bottles.

Tasting Notes:

Nose: Be cautious, the initial greeting of this whiskey’s aroma is the pungency of ethanol. However, once you become familiar with the ABV, you’ll find aromas of peanut brittle, delectable dark chocolate, and savory cooked dates wafting out of the glass for your approval.

Palate: The robust heat of this bourbon might sting at first approach, but once your taste buds acclimate there is an opulence of sticky caramel, syrup-like black cherry, tobacco leaf, and a freshly oiled leather flavor; similar to the taste you might have during the first game of spring training.

Finish: This bourbon provides as lengthy of a finish as one can anticipate. Savor it as baking spice erupts and the tiny particles of flavor collide with chunks of rich sweetness, causing a chain reaction you can still taste after 20 minutes.

Summary:

Rare Character Obliteration is a heavy-hitting bourbon that doesn’t hold back. Its rich complexity promises to surprise and overwhelm your taste buds in equal parts.

Alcohol by Volume: 57.4%

Typical Cost: $6,000

Who’s the most renowned name in the world of bourbon? You may think it’s Pappy Van Winkle. But there’s another equally renowned name – Stitzel-Weller. Its fame came from the amazing whiskey that Julian Van Winkle created for his Pappy range. However, Julian was not the only one who discovered a place for this mighty liquid. Marci Palatella entered the scene and founded the Very Olde St. Nick brand, specifically for overseas markets in the late 1980s. A particular 114.8 proof, 15-year old version is believed to have been bottled between 1988 and 1991 by Julian Van Winkle III himself, adding an interesting dimension to the story.

Tasting Notes:

On the Nose: The first impressions are sweet, with whiffs of dried cranberries and toffee, shortly followed by warm notes of vanilla and toasted oak. It’s like the captivating aroma of campfire roasted marshmallows that have just turned light brown, sandwiched between two layers of graham cracker.

On the Palate: You are first struck by the oily viscosity. But this is swiftly followed by an outpouring of lush and sophisticated flavours. Cocktail cherries, bourbon balls, butterscotch, and boozy vanilla blend perfectly with the subtle undertones 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.

ABV: 45.8%

Average Price: $5,300

In 2012, a writer referred to A.H. Hirsch’s 16-year “Gold Foil” as “the best bourbon you’ll never taste.” Since then, its legend has grown. It was initially distilled at Pennco Distillery, but surprisingly, Adolph H. Hirsch, the man who ordered the whiskey, never bottled it. Instead, Julian Van Winkle III undertook this task in 2003, spurred on by liquor store owner Gordon Hue. There are numerous legendary releases of A.H. Hirsch bourbon. However, the 16-year gold foil version had the most widespread release (2,500 cases). As a result, it elevated the brand’s popularity and led to an entire book praising its scarcity and superior quality.

Tasting Notes:

Nose: Pervasive aromas of salted caramel, golden raisins, and a generous dash of nutmeg are evident. With a little time, these merge with a well-aged oak scent and a hint of vanilla custard.

Palate: Despite its moderately mild proof, it is the concentration of flavors on the palate that instantly stands out. On the tip of the tongue, the taste of custard and golden raisins asserts itself, accentuated by salted caramel, a hint of sweet oak, and generous sprinkles of nutmeg in each rich sip.

Finish: Balance is the key aspect here, each flavor allowing for a medium-length finish instead of a drawn-out experience, enticing even more visits to the glass (and the bottle) as its understated elegance is appreciated.

Final thoughts:

Distinct from the typical, hard-hitting bourbons of today, A.H. Hirsch 16 Year instead shows off the precision of a flawlessly functioning machine. A luxurious flavor profile that instantly amazes and a medley of scents that display perfect balance, this bourbon truly embodies the principle of “less is more”. Finding it at its originally suggested retail price of $45 may prove to be a challenge though.

ABV: 57.1%

Average Price: $6,000

The current Michter’s Distillery is overseen by President Joe Magliocco. He employed some of the industry’s top experts from the get-go, all with a singular goal – to produce the finest American whiskey. In terms of America’s native spirit, Michter’s 20-Year Kentucky Straight Bourbon could arguably be seen as the brand’s most triumphant achievement.

Tasting Notes:

Nose: Indeed, this is mature bourbon at its finest. It features classic elements like black cherry sweetness, deep leather aromas, and refined oak – deviating little from these traditions.

Palate: Consistency is key with Michter’s 20 – it offers a straightforward sip with dominant flavors of black cherries, leather, and mature oak. Hints of clove and black pepper also lurk along the edges, accompanied by sweet nuances of butterscotch and vanilla extract for added complexity.

Finish: The long-lasting finish allows the alternate flavors to take a step back, spotlighting the three main flavors. Their richness is quite impressive and leaves a lasting impression.

Final Thoughts:

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.

ABV: 51.1%

Average Price: $1,400

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 peak, encapsulating a generous portion of allspice and apple pie spices (dominated by nutmeg and cinnamon), coupled with stewed red apples and a plethora of sticky caramel.

Palate: The red apples in the scent morph into a black cherry flavor on the palate, creating a deeper sweetness that fuses with the apple pie spices and introduces a hint of vanilla ice cream. The hint of oak anchors all these flavors, helping them fully bloom without overshadowing each other, thereby creating a perfectly balanced symphony.

Finish: The finish sees the oak flavor strengthen, forming a backdrop for the baking spices to come to the fore. It has a lingering aftertaste, allowing for a pleasurable deconstruction of each layer of its flavor.

Bottom Line:

Russell’s Reserve 1998 doesn’t just define a typical Wild Turkey bourbon, but it also escalates its archetypal flavors to the highest level. Moving delightfully towards the darker side of the sweetness scale, it encapsulates a complexity that its single-barrel version only dares to indicate but never absolutely attains.

ABV: 50%

Average Price: $7,000

Julian Van Winkle III is a familiar face to us, but the hallmark brand of his grandfather, Julian “Pappy” Van Winkle’s Stitzel-Weller Distillery, was Old Fitzgerald. Stitzel-Weller-produced whiskey made its way into bottles of other brands throughout the years, commanding exorbitant prices in auctions, but nothing surpasses their own reserves. In 1964, Old Fitzgerald bottles aged for a minimum of 12 years were graced with the “Very Very Old” label. For the money, these are unarguably the finest wheated bourbons ever concocted.

Tasting Notes:

Nose: The first whiff reveals the essence of candied walnuts, honey, and faintly musty oak. With a little aeration, the honey scent develops further complexity, complemented by a hint of orange peel, an abundance of brown sugar, and a subtle trace of leather.

Palate: Savouring the first sip, this phenomenal bourbon unfolds layers of candied walnuts and sweet oak across the palate, yielding bursts of clove and nutmeg at the roof of the mouth. Its oily and viscous texture allows the flavors to firmly root on the palate, maturing slowly 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.

ABV: 53.5%

Average Price: $1,800

While Russell’s Reserve 1998 may hold the title of being the best Wild Turkey bourbon ever sold in America, the Wild Turkey 14-Year Master Distiller Selection holds the title globally. Notably, this selection was primarily reserved for the Japanese export market. Bottled at 107 proof, it was limited to approximately 6,000 bottles. At its release, it was said to reflect “Jimmy Russell’s vision of the ultimate bourbon.” One sip of it justified this claim.

Tasting Notes:

Nose: In contrast to the Russell’s Reserve 1998, known more for its dark sweetness, the Master Distiller Selection is marks a perfect balance, accommodating the influence of oak, more delicate baking spices like nutmeg and clove, and semi-sweet aromas such as chocolate wafers and hazelnut.

Palate: Dark chocolate and haznut 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.