The Most Expensive Bottles Of Bourbon Ever

Three of America's greatest gifts to the West are jazz, baseball, and bourbon — not necessarily in that order. The world of whiskey is full of different styles, distillation methods, geographical contributions, and traditions, but bourbon is a pure piece of Americana.

The most basic qualification for a whiskey to be classified as a bourbon is that it must be produced in America, according to The Manuel. Bourbon must be created from a mash, or combination of fermented grain, with a content of at least 51% corn. This spirit must be aged in American oak barrels and enter that barrel at no higher than 125% alcohol. Nothing other than water can be added before bottling, and the final product must be at least 40 proof. While the exact origin of bourbon is not exactly clear, the spirit dates back to 18th-century Kentucky. Today, it's a $3.7 billion industry.

There are many quality bourbons available for less than $50, but small batch bourbons aged extensively in limited quantities are the most sought after. Here are 15 of the most expensive bourbons on the market today; these are the ones you may need a bank loan to purchase.

With generations of distilling dating back to the 18th century in his DNA, William Larue Weller opened his own distillery in 1849. After Weller's passing in 1908, the famed "Pappy" Van Winkle purchased the company.

With the start of Prohibition, the company merged with APH Stitzel Distillery, and the legendary Stitzel-Weller Distillery was born. Soon after their official opening on Derby Day in 1935, the distillery gained widespread acclaim and popularity for its wheated bourbon recipe, where wheat grain is used in the cooking mash instead of rye, making for a more palatable, silky smooth bourbon. Today, Buffalo Trace Distillery claims ownership of the storied bourbon brand and continues to sell a variety of bottled recipes passed down from W.L. Weller, himself.

William Larue Weller Kentucky Straight Bourbon Whiskey is hand-bottled, uncut, and unfiltered at barrel proof. This bourbon's price tag is not reflective of its taste alone, but the long standing resilience, tradition, and innovation it represents. A bottle can be purchased today for $2,400.

Like many other bourbon distillers keen on taking advantage of a new, growing industry, Kentucky Owl founder Charles Mortimer Dedman was doing great until Prohibition, according to The Whiskey Wash. Founded in 1879, Kentucky Owl Sour Mash Bourbon distillery was a successful business up until 1916, when the U.S. government ordered a cease of production and shipment of all liquor to government-owned warehouses. Mysteriously, those warehouses burned to the ground, their contents lost forever. Dedman never distilled again.

Nearly 100 years later, in 2014, Kentucky Owl Bourbon saw its renaissance by Dedman's great-grandson, Dixon, and two business partners. Their first product was a combination of sourced, aged stocks of bourbon reentered into newly charred barrels and aged once again. Only 1,300 bottles were filled, each label reading "Kentucky Owl Bourbon Batch 1."

Initially, Kentucky Owl Batch 1 was priced at around $175 a bottle, given its unique history and limited stock. Soon thereafter, a Southern culture magazine called Garden & Gun awarded Kentucky Owl Batch 1 the prestigious "Made in the South" award. The acclaim expanded the bourbon's popularity even further. With only 1,300 bottles available at its release and the passing of over seven years since then, a bottle of Kentucky Owl Bourbon Batch 1 is now priced at over $3,000.

The Heaven Hill Distillery, established in 1935, became and remains an institution of bourbon. Today, Heaven Hill is the world's largest independent, family-owned bourbon distillery.

This particular bourbon gets its name from John E. Fitzgerald, a Treasury Agent who was granted unmonitored access to a warehouse full of bonded bourbons. According to The Whiskey Jug, Fitzgerald helped himself to the finest bourbons he could find and the barrels he selected became known as "Fitzgerald barrels," the contents of which were used for a very soft, wheated bourbon that was named "Old Fitzgerald."

John E. Fitzgerald Very Special Reserve was acquired by Heaven Hill when they purchased the iconic Old Fitzgerald brand in 1999. Originally distilled and barreled by the Stitzel-Weller distillery in 1992, this bourbon was aged for seven years before relocation to Heaven Hill, where aging continued all the way until 2013. This highly exclusive and rare 20-year maturation contributes to the expensive price tag of a bottle of John E. Fitzgerald Very Special Reserve, going today for $3,500.

Speaking of Old Fitzgerald, this "very old" bottle is another sought after collector's item by whiskey enthusiasts. The main reason for its value comes from its association with the Stitzel-Weller distillery and "Pappy" Van Winkle, according to L.A. Whiskey Society. Another reason is that most labels of Old Fitzgerald Very Old Bourbon are personalized. Releases of the Very Old Collection, ranging from 8 to 18 years of age, were specifically bottled for and sold to certain people and organizations.

Old Fitzgerald Very Old bourbons began being distilled sometime in the middle of the 20th century until 1972. Fifty years later, there are very few left and the recent "bourbon boom" of the past decade certainly reduced the finite stock even further. Today, the only way to get a bottle of this bourbon is through a specialty or private seller, but private auctioneers take a large percentage of sales for themselves, causing the price to rise higher than its actual value. Luckily, a bottle of Old Fitzgerald Very Old Bourbon is available here, but it'll cost you nearly $6,000.

This bourbon is another courtesy of Heaven Hill Distillery. Every year, Heaven Hill Distillery releases an addition of the Parker's Heritage Collection, an homage to the distillery's late Master Distiller, Parker Beam. Most of the barrels used for Heaven Hill whiskeys are charred for 40 seconds. The black-charred layer on top acts as a natural charcoal filter, while the red layer below it infuses the spirit with its caramelization. Barrels used for bourbons in the Parker's Heritage Collection are charred for a full 90 seconds. This elongated blast of heat causes the top layer of the oak to actually break down and pull apart. This allows the bourbon to interact more with the caramelized and uncharred layers of the barrel, making for an even more enhanced aroma, flavor, and texture.

Heaven Hill Distillery has now released 15 editions of their Parker's Heritage Collection, but their oldest bourbon remains their best. This second edition may be a stiff 96 proof, but its 27-year maturity in these deeply charred barrels make for a bourbon so smooth its alcohol will be hard to detect. The Parker's Heritage Collection has the accolades to back it up, and a single bottle is worth $6,000.

A.H. Hirsch Reserve Straight Bourbon begins our top 10 of the most expensive bottles of bourbon ever, and it may be the most mythological of this list, too, according to The Whiskey Wash. This bourbon was initially distilled in 1974 at what eventually became the Mitcher's Distillery, in Schaefferstown, Pennsylvania. The bourbon was produced for a 400-barrel stock with a standard recipe of 75% corn, 13% rye, and 12% malted barley. Once the distillery shut down due to bankruptcy, the already extensively aged bourbon was acquired by Gordon Hue, who commissioned Julian Van Winkle III to bottle the bourbon as A.H. Hirsch Reserve. There have been multiple bottles released of this bourbon, with the first 16-year-old bourbon dating back to 1991 and featuring a label from Lawrenceburg, Kentucky.

The main reason for the high price of this bottle is its finite nature. There is only as much as is left from the batch made in 1974 — and that is it. Its 16-year aging process makes for a surely smooth spirit, but the price point comes mainly from the fact it will not be around forever. Anyone who decides to take advantage of the limited supply can expect to pay at least $9,000 for a bottle.

The Buffalo Trace O.F.C. Bourbon pays homage to the O.F.C. distillery opened all the way back in 1870. When in operation, the O.F.C. distillery was a hub for technological innovation. It was one of the first distilleries to feature copper fermentation vats, column stills, and the very first to use a steam heating system, which is still used in Buffalo Trace's aging warehouses today.

Buffalo Trace began distilling bourbons in homage to the O.F.C. distillery as part of their vintage series four decades ago in 1980. In 2020, Buffalo Trace released their bourbon distilled in 1995 in a limited capacity of just 1,500 bottles. As anticipation grew with each new release year after year, the demand for this bourbon started out very high and it became very rare soon after. Today, a bottle of Buffalo Trace O.F.C. 25 Year Bourbon will cost you at least $13,000.

In 1936, the Willett Distillery was erected on the Willett family farm in Bardstown, Kentucky. Less than three decades later, the Willett Distillery filled its 100,000th barrel. Since then, the Willett Distillery has bottled a variety of bourbons all striving to achieve a pinnacle of quality.

The Willett Family Estate Bottled Bourbon sets itself apart from the distillery's other spirits, however. Aged for 21 years before bottling, this bourbon is the perfect encapsulation of everything Willett represents. The perseverance and patience required to produce a bourbon so mature and high quality is a testament to the long journey the Willett Distillery has undertaken and continues to ride.

The Willet family emblem torched by Edward Willett over four centuries ago in London after completion of his pewter apprenticeship dawns the bottle's label, a reminder that the price tag represents more than the contents. A single bottle of the Willett Family Estate 21 Year Bottled Bourbon can be purchased for upwards of $15,000.

The Last Drop Distillers was founded in 2008 by Tom Jago and James Espy, two icons in the spirits industry who set out to provide the most extraordinary spirits in the world. The Last Drop's Buffalo Trace Kentucky Straight Bourbon is the second bourbon bottling of the distillery. Although the name "Buffalo Trace" is just over a couple decades old, the distillery, located in Frankfort, Kentucky, is formerly known as the George T. Stagg Distillery and remains the oldest continuously operating bourbon distillery in the world.

When the distillery was sold to the Sazerac Company in 1992, the new ownership took possession of the entire operation in its then current state. In the corner of one of the warehouses lay a few parcels of bourbon, one of which landed in the hands of The Last Drop. The bourbon, distilled in 1980, gained a deep and rich color after 20 years of aging in its barrel completely undisturbed. Today, the limited result of such patient maturation can be purchased today for around $22,000.

Eagle Rare is another bourbon coming from the legendary Buffalo Trace distillery. This bottle is the third edition of a series by Buffalo Trace by the same name, with the first Double Eagle Very Rare releasing in 2019, according to The Bourbon Finder. This bourbon is matured for two decades, twice as long as the standard Eagle Rare Bourbon. Each bottle of Double Eagle Very Rare is bottled in a handmade decanter and placed in its own presentation box with sliding doors.

This edition of Double Eagle Very Rare is different from its two predecessors. It has a higher proof of 101, an homage to the original proof of Eagle Rare Bourbon when it first began distillation in 1975. Only 199 bottles of Double Eagle Very Rare were released to the market and the suggested retail price at the time of its launch was an already expensive $2,000. The demand and quick action of enthusiasts and connoisseurs have multiplied the value of the few remaining bottles by more than 10. A bottle today will cost you $23,000.

As with all bourbon whiskeys, Michter's Kentucky Straight Bourbon is stored in charred, white American oak barrels. However, the wood used for these barrels is dried for up to four years before crafting. This allows the wood's natural properties to enhance further than in typical dehydration times, making for a more dense flavor profile.

Despite the industry's usual proof level of bourbons being at least 125, Michter's bourbon enters its barrel at 103. This lower entry proof was actually historically considered the highest standard and allows the flavoring of the charred oak to dissolve more evenly and frequently throughout the bourbon.

Michter's also utilizes the rare practice of heat cycling, that is, raising and lowering the temperature of the aging warehouse periodically, which causes the bourbon to contract, enter the wood inside the barrel deeper, and absorb more flavor. Heat cycling is very costly and, combined with the lower entry proof, yields less bottles per barrel. This lessened supply is why a bottle of Michter's 25 Year Old currently goes for over $23,000.

Colonel Edmund Haynes Taylor Jr. lives on as an icon of American bourbon whiskey. In 1860, he invested in Old Crow, the first ever sour mash bourbon, according to Connosr. Soon thereafter, Taylor took his newfound discovery and advanced bourbon making even further. Instead of adding sour mash from the previous batch, like usual, he began allowing newly cooked mash to rest before fermentation. In this three- to five-day period, the pH of the mash lowers naturally, making for an entirely pure production.

E.H. Taylor Jr. eventually took over the Old Crow distillery and founded many others, including the one now known as Buffalo Trace, the distillery that sells Taylor's Old Fashioned Sour Mash today. This bottle, distilled in 2002, is a modern replication of Taylor's natural sour mash method. The finished product is a complex bourbon worthy of a Gold Medal in the Fifty Best Bourbons competition of 2012. A decade and counting later, supply is even more limited, so a single bottle will cost you $29,000.

The name "Van Winkle" goes with bourbon the way "Johnny Walker" goes with scotch. In 1910, "Pappy" Van Winkle purchased the Stitzel Distillery in Louisville, Kentucky. Even through Prohibition, Van Winkle's distillery carried on with production. In the early 1970s, then Stitzel-Weller Distillery sold the rights to all of their brands except one, the Old Rip Van Winkle bourbon predating Prohibition. Julian Van Winkle Jr, Pappy's son, took over and resurrected this recipe and began distilling again in 1972.

This particular bottle of the Van Winkle Family Reserve ranks third on our list of the most expensive bourbons. It was bottled by Julian Van Winkle III in 1990 after 16 years of aging at his own distillery, Old Commonwealth. This family reserve was sourced from Boone Distillery, where it was distilled in 1974. The Old Commonwealth continued bottling these rare bourbons until 2002, when the Sazerac company took over following a thinning of stocks, per The Bourbon Concierge. The new ownership warehoused this Van Winkle Family Reserve and continued to distill the Van Winkle Family Reserve using the old recipe. Today, a very limited number of bottles containing the original bourbon from the Boone Distillery still remain and they currently go for $30,000.

The age of a bourbon is attentively considered. Redemption 36 Year Old pushes the boundary of time and stands its test unparalleled. This bourbon is known to be one of, if not the oldest, bourbons ever released to the public market. According to The Whiskey Wash, Redemption 36 Year Old is part of the distillery's "Ancients" collection, which features a rye and bourbon whiskey distilled and barreled in 1998 and 1978, respectively. These whiskeys were produced at the Seagram's distillery in Lawrenceburg, Indiana, the same site in which every drop of Redemption Whiskey has ever been distilled.

The distillery's stock of Redemption Bourbon was so scarce, the amount left after its near four-decade-long maturity was only enough to fill 18 bottles, each of which is silk-screened with rye fronds and showcases a hand-painted metal label. The hand-bottled decanters are finished with leather cording, and sealed with a cork containing a real 1978 U.S. penny, commemorating the year the bourbon was distilled. At its release in 2014, the retail price of one of the 18 bottles was $1,200. Today, the price of a single bottle of Redemption 36 Year Old is a good deal more expensive at $45,000.

The Van Winkle name is a bourbon institution, and this is the holy grail. This is the oldest Old Rip Van Winkle bourbon to ever be released, according to Whiskey Advocate. At 25 years old, this bourbon filled just 11 barrels in 1989 at the Stitzel-Weller Distillery. In 2002, they were moved to and warehoused at Buffalo Trace.

Of the 11 barrels filled, just 710 hand-cut glass decanters were available, each of which was packaged in a handcrafted wood box containing staves from the original barrels the bourbon sat inside of for 2 ½ decades. Even more, each purchase of Old Rip Van Winkle 25 Year Old bourbon comes with a certificate of authenticity from "Pappy" Van Winkle's grandson, himself.

At its initial release back in 2017, the suggested retail price of a bottle was $1,800. Predictably, they flew off the shelves, many of which had to be reserved ahead of time. Today, the price of one bottle of Old Rip Van Winkle 25 Year Old bourbon is a staggering $65,000, clearly making it No. 1 on our list of the most expensive bourbons ever.