What’s the most important bourbon of all time?
That, of course, depends on how you determine import. Merriam-Webster defines it as such: “marked by or indicative of significant worth or consequence.” Armed with that definition, we can say that “worth” doesn’t strictly boil down to cost. Indeed, some of the most important bourbons of all time are/were bottom-shelf offerings, some of which can still be purchased today for less than $30.
This list will focus strictly on bottles of historical importance, expressions that helped transform the industry, establish new standards, and alter the course of the industry as we know it. Some of those are extremely rare or even possibly extinct, while others are sitting on your local liquor store’s shelf right now, but no matter the availability or price, these all have one thing in common: they changed the bourbon world as we know it.
Let’s dive into it and rank the 21 most important bourbons ever made!
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21. Michter’s Toasted Barrel Bourbon
ABV: 45.7%
Average Price: $140
What Makes It Important:
Michter’s Master of Maturation, Andrea Wilson, deserves more credit than anyone in the industry for creating and then popularizing “toasted barrel bourbon.” The process, which involves a barrel being held over a flame but, crucially, not being charred, unlocks a different degree of wood sugars that imparts a wholly unique flavor profile on the end product. That end result brings forth flavors like marshmallow, honey, campfire smoke, and coconut shavings and has caught on like wildfire throughout the industry, with innumerable brands joining the trend that Michter’s began with this 2014 release.
20. Angel’s Envy Bourbon
ABV: 43.3%
Average Price: $42
What Makes It Important:
Angel’s Envy Bourbon is historically significant, not for inventing finished bourbon, but for being the first brand to offer an evergreen expression of finished bourbon as part of its core lineup. That bold decision was initially met with intrigue but has since blossomed into a practice that countless other brands have adopted, culminating in an industry-wide trend to push the boundaries of finishing we’ve seen over the past few years.
19. A.H. Hirsch 16-Year Bourbon
ABV: 45.8%
Average Price: $5,000
What Makes It Important:
The Gold Foil version of A.H. Hirsch’s 16-Year Bourbon is best known today by the moniker bestowed upon it by whiskey writer Chuck Cowdery, who wrote an entire book extolling its virtues titled “The Best Bourbon You’ll Never Taste.” The story of A.H. Hirsch 16-Year begins with…Ultimately what makes this bourbon so historically important, impressive quality aside, is that it’s one of the most prominent bourbons to develop a cult following on the internet.
Denizens of StraightBourbon.com (including Chuck Cowdery) helped to drive consumer interest in this hidden gem, a process that we’ve since seen repeated time and again with the rise of more internet-based bourbon clubs, Facebook groups, and influencer-approved limited editions. Again, it’s a trend that some may frown upon, but all the same, this release is one of historical import for that reason and others.
18. Four Roses Single Barrel Bourbon “Goykh Smash”
ABV: 60.3%
Average Price: ??
What Makes It Important:
This expression is so under-the-radar that we weren’t even able to find pictures of it online, and everything is online. Shout out to our connect for the image above. The Goykh Smash Four Roses Single-Barrel Selection is historically significant because it’s the bottle most widely credited with introducing private label stickers (erstwhile known as “tater stickers”) to the bourbon industry. The story goes a little something like this: Steven Goykhberg was a prominent member of the early aughts bourbon collector scene, and he selected this barrel of Four Roses and then put one of the early examples of a tater sticker on the bottles. It features a photo of Hulk “smashing” the ground with the words “Goykh Smash” above it with “I Don’t Fool Around” below.
While pretty much all photos of this pick have seemingly been scrubbed from the net, you’ll still hear early collectors speak in reverent tones about the bottle that many people credit with transforming the marketing of single-barrel selections. As a final note, Four Roses has since instigated a “non-mutilation” policy, kicking anyone who adds a sticker or other adornments to their single-barrel selections out of their single-barrel program. That development makes early Four Roses bottles with tater stickers all the more attractive to after-market collectors.
17. Parker’s Heritage Collection 1st Edition Cask Strength Kentucky Straight Bourbon Whiskey
ABV: 63.7%
Average Price: $5,800
What Makes It Important:
These days, it’s quite common to see bourbon and charitable causes linked, but while people have long been using rare bottles to raise money for good causes, Parker’s Heritage is one of the key releases that brought the idea to the mainstream. In 2010, Parker Beam, Master Distiller at Heaven Hill Distillery, was diagnosed with amyotrophic lateral sclerosis (ALS).
Shortly after that, this expression was created and launched in 2007 as a way to both honor Parker’s contributions to the industry (he was part of 2001’s inaugural class of the Kentucky Bourbon Hall of Fame) and to donate money to the research and eradication of ALS. Those charitable efforts continue today with each release of Parker’s Heritage, though sadly, Parker passed away in 2017, his legacy is alive and well.
16. Wild Turkey 12-Year 101 Bourbon “Cheesy Gold Foil”
ABV: 50.5%
Average Price: $1,800
What Makes It Important:
Wild Turkey 101, perhaps more than any other offering, helped maintain the bourbon industry’s viability in the global market through the lean years of the 70’s and 80’s. While domestic sales of bourbon were in the toilet during those decades, it was the inventiveness of distilleries and the explosion of the foreign market, primarily Japan, that kept many of bourbon’s most storied producers in business.
For Wild Turkey, that meant offering their 101-proof bourbon in stylish decanters, which did little to abate the public’s waning interest but have persisted as a cool historical idiosyncrasy, and exporting a large volume of its flagship liquid overseas. The success of bourbon’s sales in Japan helped keep them and other companies afloat and produced some now-legendary expressions that might not otherwise exist if it weren’t for Wild Turkey spearheading the movement. One of the most revered expressions to come out of this era, nicknamed “Cheesy Gold Foil,” has remained one of Wild Turkey’s most sought-after expressions to this day.
15. Willett Family Estate 28-Year-Old Bourbon Barrel #1056
ABV: 64.4%
Average Price: $11,875
What Makes It Important:
Willett Family Estate is now known as a legendary name in the bourbon industry, and they built that mythical status thanks to their incredibly well-regarded vault of hyper-aged sourced whiskey. Bottles like Doug’s Green Ink and LeNell’s Red Hook Rye put the brand on the map and now regularly sell for 5-figures at prestigious auction houses, but Willett’s cache of 20+ year bourbons also garner plenty of acclaim.
Case in point: when this expression was released, it was Kentucky’s oldest single-barrel bourbon ever bottled. Selected by Pacific Edge and distilled in 1980 from an undisclosed source before being bottled in 2008, if there’s one bottle of bourbon most emblematic of Willett Family Estate’s early grasp on the single-barrel market, gobbling up excellent, old bourbon from far-flung sources and driving the demand for such increasingly rare liquid, it’s this bottle right here.
14. Weller Special Reserve Wheated Bourbon
ABV: 45%
Average Price: $97
What Makes It Important:
We can keep this one short and simple by saying Weller is typically cited as the earliest example of “wheated bourbon” to grace the market. As it goes with pretty much every claim to a “first” in the bourbon world, there are some who would dispute that claim, but at the very least, Weller has done the most to popularize the style since its inception in 1849. We have William Larue Weller to thank for this expression, and as you may know the current-day version of Weller Special Reserve is produced by Buffalo Trace who has furthered the reputation of wheated bourbon thanks to the success of both its Weller and Van Winkle lineup of whiskeys.
13. Evan Williams Bourbon
ABV: 43%
Average Price: $28
What Makes It Important:
What makes Evan Williams Bourbon so significant is that it was produced by Kentucky’s first legally registered commercial distillery by the Welsh immigrant whose name adorns every bottle. Not only was Evan Williams the first man on the scene for what would become the epicenter of bourbon for generations to come, but Evan Williams Bourbon remains to this day one of the world’s best-selling bourbons, seldom leaving the top three in global sales annually.
12. Jim Beam Distiller’s Masterpiece (1999)
ABV: 49.5%
Average Price: $1,800
What Makes It Important:
Jim Beam’s Distiller’s Masterpiece was one of American whiskey’s biggest game-changers. The expression, launched in 1999, marked a number of significant milestones as one of the first super-premium bourbons to be released with a price point of $200+ and the first prominent example of a super-premium finished bourbon. This offering was so ahead of its time that it sat on shelves for months, despite being an artful collaboration between Jim Beam Master Distiller Booker Noe and Cognac pioneer Alain Royer that has since gained contemporary acclaim for its prescience as well its superlative quality.
While not everyone will see this release in a positive light, given the fact that it spawned a proliferation of high-priced progenitors in the finished bourbon category of uneven quality, there’s no denying that its release was a watershed moment in the contemporary bourbon industry.
11. Smooth Ambler Old Scout Single Barrel Bourbon (MGP Sourced)
ABV: 55.9%
Average Price: $300
What Makes It Important:
A bit of a curveball on this list; this is another one of those representative choices that speaks to a wider trend. These Smooth Ambler Old Scout Single Barrel expressions in the 12-year age range, sourced from MGP in Indiana, drove the bourbon world crazy when they first hit shelves. While there had been earlier examples of stellar, sourced MGP bourbon on the market, this was definitely the tipping point that drove consumers into a craze, hunting this expression into extinction.
Since these bottles first hit shelves, there have been countless brands built with MGP-sourced liquid, whether they eagerly disclose that fact or not, and with MGP now situated as perhaps the biggest producer of sourced bourbon in the industry (they don’t disclose such details publicly) it’s safe to call the Smooth Ambler tipping point a crucial one for the contemporary market, driving popularity and demand for MGP juice, and proving its viability.
10. Old Crow Chessman
ABV: 43%
Average Price: $2,300
What Makes It Important:
The Old Crow Chessman series is emblematic here of several critical developments in the industry. For one, in 1969, during the lean period when these were produced and domestic whiskey sales were in the tubes, decanters became all the rage to spruce up American whiskey’s presentation. The Old Crow Chessman were some of the most ostentatious and ambitiously packaged whiskeys of all time, coming in a fully functional chess set with an oh-so-70s shag rug with black and white squares to play on.
Another aspect that makes this series historically important is its tangential ties to the man who founded Old Crow, James C. Crow. Dr. Crow is widely credited as being the man to introduce or at least popularize the sour mash process in the bourbon industry. Though Crow passed away long before this expression was created (it was sold in 1969 by National Distillers, and the Old Crow brand is today owned by Jim Beam), this was one of the last prominent releases to bear his name before Old Crow became a bottom-shelf offering, not worth exploring. More than that, in fact, this is frequently cited by critics as one of the best bourbons of all time.
9. Eagle Rare 25
ABV: 50.5%
Average Price: $45,000
What Makes It Important:
I’ll be the first to admit that this selection is speculative, but here’s the path to historical import for Eagle Rare 25. Joined by Weller Millenium (which isn’t officially a bourbon) in Buffalo Trace’s uber-premium range, Eagle Rare 25 is historically significant not just for being a hyper-aged expression but also for the process that produced it. This expression spent the first decade of its life destined to be Eagle Rare 10-Year Single Barrel Bourbon before graduating past that mark to be earmarked as a future Eagle Rare 17 release. Having aged beyond 17 years, it was then eligible to become Double Eagle Very Rare, but at the 20-year mark, the whiskey that wound up in this release was moved to Buffalo Trace’s experimental Warehouse X, a climate-controlled aging facility which the distillery hopes will allow them to push the ages of future releases beyond 25 years, perhaps as high as 50 or more.
As the first step toward that ambitious goal, Eagle Rare 25 is easily the most historically significant bourbon released in the last two years. Going one step further, the case can be made that this uber-premiumization of the category could become a thing of the future in line with Distiller’s Masterpiece helping to create the super-premium market as it exists today. If successful, Eagle Rare 25 will mark the opening salvo in that effort to put hyper-aged bourbon expressions on par with offerings in the same age range from Scotch and Japanese distilleries.
8. Blanton’s Single Barrel Bourbon
ABV: 46.5%
Average Price: $110
What Makes It Important:
The expression that most bourbon enthusiasts cite as the one that put single-barrel bourbon on the map is Blanton’s. Not only did this brand’s popularization of single-barrel bourbon completely revolutionize the American whiskey landscape, leading to scores of imitators, but it’s also remained one of the most commonly sought-after bourbons on the market today. The popularity of Blanton’s (aided, in part, by its prominent place in the John Wick movie franchise) has been another of the pivotal moments in recent bourbon history that created the craze that it is today.
7. Old Forester President’s Choice
ABV: 60%
Average Price: $1,600
What Makes It Important:
While many people cite Blanton’s as “the first single-barrel bourbon,” there’s an important distinction to note there, as Blanton’s was actually the first bourbon to be commercially marketed as a single barrel. In fact, Old Forester’s President’s Choice is generally considered the world’s first single-barrel bourbon, debuting back in 1962 as a unique expression of hand-selected casks from Old Forester’s President, thus the name.
6. Pappy Van Winkle 20-Year Bourbon
ABV: 45.2%
Average Price: $3,000
What Makes It Important:
The 20-year version of Pappy Van Winkle is teeming with historical significance. This offering was the first to be bottled in the celebrated Pappy Van Winkle lineup, which now stands as perhaps the most widely sought-after lineup in the entire bourbon world when it hit the shelves back in 1994. The culmination of several earlier iterations by Julian Van Winkle III, this expression was initially utilizing liquid sourced from Old Boone Distillery (a little-known-fact gaining more widespread attention thanks to soothsayers like Gil Schwarz) and was the first bourbon to receive a 99-point rating from the Beverage Testing Institute in 1997 in Wine Enthusiast Magazine.
One can also make the case that this expression was pivotal in launching the bourbon boom as the late chef Anthony Bourdain’s proclamation that “if God made bourbon, this is what he’d make” on his show The Layover back in 2012 helped send the fervor around the brand into hyperdrive, fueling today’s bourbon mania.
5. Jack Daniel’s Tennessee Whiskey
ABV: 40%
Average Price: $27
What Makes It Important:
Sure, you may just see Old No. 7 for what it is, the most ubiquitous American whiskey on the planet, and for that reason alone, it’s certainly important to the history of the category. Jack Daniel’s goes a step further, however, as the whiskey that popularized — perhaps even invented — the Lincoln County Process, which is the backbone of the Tennessee whiskey category. A quick obligatory note for any time one discusses Jack Daniel’s: yes, it is technically a Tennessee whiskey, but that doesn’t mean it isn’t a bourbon. Some people will argue this point with you until they’re blue in the face, but the facts are simple: Jack Daniel’s is made to the regulations of bourbon, which means it is legal to label it as such, but the Lincoln County Process ALSO makes it legally a Tennessee whiskey, while not stripping it of its status as a bourbon. The difference may seem negligible to some, but it’s a constant point of contention worth dispelling here.
One last bit that makes Jack Daniel’s important is the brand’s more recent embrace of Nearest Green, a formerly enslaved man who they believe taught Jack Daniel (the man) how to filter his whiskey in what became known as the Lincoln County Process. As the most prominent American whiskey brand on the planet (and arguably the biggest bourbon brand), there can be no debate about Jack Daniel’s importance to the category.
4. Very Very Old Fitzgerald Blackhawk Edition
ABV: 60.5%
Average Price: $80,100
What Makes It Important:
Very Very Old Fitzgerald is a now-discontinued line of wheated bourbon from the famed Stitzel-Weller Distillery, aged for either 12, 15, 16, or 18 years. This particular bottling was created to honor the family that owns the Chicago Blackhawks organization, which in itself isn’t historically significant. What is, however, significant is that this rare bottling is considered one of the hardest-to-find expressions in the vaunted lineup, which led to it becoming the highest-priced bourbon ever sold at auction earlier in 2024, fetching a whopping $80,100 before fees and taxes. While the sale has since been surpassed (by a Van Winkle Single Barrel Bourbon) this bottling remains indicative of bourbon’s continuing rise to prominence in the global whiskey space and reflective of just how coveted some of the most acclaimed expressions of America’s Native Spirit have become.
Of further historical significance is the Old Fitzgerald lineup’s role in popularizing Bottled in Bond bourbon. It first began as a bonded bourbon in 1904, but things really picked up post-Prohibition when Old Fitzgerald became the Stitzel-Weller Distillery’s flagship bourbon, with Very Old Fitzgerald and eventually Very Very Old Fitzgerald joining the lineup. It should be noted, however, that all of the Old Fitzgerald bourbons were bonded products in Julian Van Winkle’s lifetime, though we began to see higher-proofed options (like this Blackhawk single-barrel) after he passed in 1965.
3. Old Forester Bourbon
ABV: 43%
Average Price: $19
What Makes It Important:
Old Forester has a well-loved portfolio of high-quality bourbons today, but what makes their entry-level offering perhaps the most historically significant of all boils down to one thing: it was the first commercially available bourbon to promote the fact that it was exclusively sold in glass bottles. That little innovation quickly became an industry standard that pervades to this day and would mark the first of Old Forester’s two revolutionary marketing tactics over the course of its 150+ year history, with the second being the introduction of single barrel products.
2. Maker’s Mark Bourbon
ABV: 45%
Average Price: $30
What Makes It Important:
Maker’s Mark is a bourbon borne from the minds of the Samuels family, and as history tells it, they settled on the iconic wheated mash bill after baking several batches of bread with different grain recipes. As one of the most historic distilleries to only ever produce a single mash bill and never sell their liquid to other brands, Maker’s Mark is significant, but the real hook is the way the brand transformed the industry with its emphasis on tourism.
Margie Samuels designed Maker’s Mark’s distillery to be a visiting place for a tourist industry that didn’t yet exist but, through her visionary work, became a multi-billion dollar industry that netted her a posthumous Kentucky Bourbon Hall of Fame induction in 2014. Of lesser, but still notable, significance was Margie’s decision to use the iconic red wax that adorns each bottle for which Maker’s Mark is known. They remain the only brand whose specific use of wax (red, with dripping tendrils) is protected from imitation. For dawning a new age of branding and tourism while standing as an exemplar of quality in American whiskey around the world, Maker’s Mark is one of the most important bourbons of all time.
1. Booker’s Bourbon
ABV: Varies by batch
Average Price: $120
What Makes It Important:
Any savvy bourbon enthusiast today will note the prevalence of cask-strength offerings on the market, and if you’re wondering where it all began, look no further than 1988, which witnessed the first commercially available release of Booker’s. Booker Noe, the brand’s creator, had been personally bottling and wax dipping some of his favorite bourbon barrels from the “center cut” of Jim Beam’s voluminous warehouses for years, giving them out as Christmas gifts to friends and beloved employees.
However, when the popularity of “Booker’s bourbon” caught on, it became inevitable that those special selections would go on to become a commercially available product. Once it hit the market, Booker’s became the most prominent example, if not also the first example, of cask-strength, undiluted bourbon to hit liquor store shelves. While tastes at the time were less adapted to absorb all that high-octane alcohol, barrel-proof bourbon has since become a huge craze, with offerings in that style proliferating across seemingly every brand in America.
Booker’s, as part of Jim Beam’s Small Batch Collection, also marked one of the first times the phrase “small batch bourbon,” which was coined by Booker Noe himself, was used to market what was at that point already a prevalent practice of producing bourbon in batches. You can even use the creation of Booker’s to trace the genesis of the rise of “hazmat” offerings and increased appreciation of full-flavored bourbon, which continues to this day. It’s all of these factors that make Booker’s the most important bourbon of all time.