The 25 Best Bourbons of the 21st Century (So Far)

Bourbons have become increasingly collectible. Here are the ones you need to stash away.

Maker’s Mark Bourbon Photo: Courtesy of Maker's Mark

There’s much to love about the world’s great Japanese, Scotch and Irish whiskey distilleries. But when it comes to innovation, the wily bourbon producers in the United States have been leading the way for years. In Kentucky and beyond, purveyors of America’s native spirit have refused to let the excellence of their existing products stand in the way of coming up with new ones. And over the last decade and a half, a plenitude of incredible new whiskey with a mash bill of at least 51 percent corn and aged in charred new oak barrels—the house rules for a whiskey to be called a bourbon—has come to market, some from brand-new producers, others new expressions from venerated houses. Fortunately, we’ve got you covered. Here are 25 of the best bourbon releases of the last 20 years.

E. H. Taylor, Jr 18-Year-Old Marriage

E. H. Taylor, Jr 18-Year-Old Marriage

Photo: courtesy Caskers


The late Colonel Edmund Haynes Taylor, Jr. never actually served in the military—his was an honorary rank, bestowed in kind upon Taylor’s fellow Kentuckian Harland Sanders, of fried fowl fame. But make no mistake, E.H. Taylor Jr. was no chicken; he was a fighting man who battled hard to get the Bottled-in-Bond Act of 1897 passed. This delightful 100-proof BIB whiskey from Buffalo Trace is an homage to the legendary Taylor, known as the founding father of the modern bourbon industry. The whiskey smells like butter cake drizzled with cinnamon (enjoyed in a sauna) and tastes like a vanilla sundae topped with caramel and nuts, only boozier. Finishes with a burst of Wrigley’s spearmint and a dash of pepper, aka the chewing gum that should have been.

Buy Now: $2,888

Four Roses Al Young 50th Anniversary Small Batch Bourbon

Four Roses Small Batch Bourbon

Photo: Courtesy of Four Roses

Kentucky Distillers’ Association Hall of Famer Al Young toiled for 50 years at Four Roses, and for his efforts, they named a whiskey after him. Beats a gold watch, right? A blend of four distinct proprietary recipes, the “Al Young,” as it’s affectionately known, exhibits aromas of sweet caramel and floral honeysuckle. The palate offers fresh peach and apricot flavors, encompassing luxurious, warm fig and rich oak, with a hint of mint on the finish. It was originally priced at $150, but expect to pay significantly more on the secondary market.

Buy Now: $1,951

Old Forester 150th Anniversary Bourbon

Old Forester 150th Anniversary Bourbon

Photo: courtesy Old Forester

Liquor lore has it that George Garvin Brown revolutionized the whiskey business in 1870, when he started selling his “Old Forrester” bourbon in sealed glass bottles instead of the barrels and jugs that were the norm back then. Fifteen decades and a discarded “r” later, ol’ George’s hooch is still going strong, as evidenced by this estimable expression, which is available in three batches in very limited quantities. Batch 01/03 is a 125.6 proof fruit bomb with a graham cracker finish. Batch 02/03 weighs in at 126.4 proof and is sweet and spry as the day is long. Last but not least, Batch 03/03 — 126.8 proof and brimming with spice and citrus.

Buy Now: from $250

Barrell Bourbon Batch 009

Barrell Bourbon

Photo: Courtesy of Barrell Craft Spirits

Barrell Craft Spirits was founded in 2013 and quickly became one of the most buzzed-about producers of American whiskey. Released in 2016, today Barrell Bourbon Batch 009 can most easily be acquired on the secondary market. Distilled in Tennessee and aged in Kentucky, it’s a 112-proof flavor bomb, offering everything from tropical fruit to thick clotted cream. This bourbon possesses a familiar warmth, like a favorite old blanket or pair of wool socks. The boundless finish is reminiscent of sweet buttered caramel corn.

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Angel’s Envy Cask Strength Bourbon Finished in Port Barrels


Angel’s Envy Bourbon cask strength

Photo: Courtesy of Angel’s Envy

Legendary master distiller Lincoln Henderson released this Angel’s Envy cask-strength expression to great acclaim in 2012. It turned out to be his swan song. Henderson passed away in September 2013, leaving a legacy of artistry and innovation that will not soon be forgotten. The Port Barrel–finished whiskey is a magnificent testament to his abilities. After six years spent resting in new white American oak, the spirit was refined in 60-gallon ruby port barrels made from French oak and imported directly from Portugal. European influence aside, this is still the epitome of complex, bold Kentucky bourbon. The palate teems with flavors, from raisin to banana to rich dark chocolate. A clean and lingering finish offers a hint of Madeira that slowly fades. At 124.5 proof, it packs a serious wallop.

Buy Now: $343

Rabbit Hole Dareringer

Rabbit Hole Dareringer

Photo: courtesy Rabbit Hole

This gorgeous Straight Bourbon Whiskey from Kentucky is finished in Pedro Ximenez sherry casks produced at Casknolia, a cooperage in the small Spanish town of Montilla. It’s what’s known as a wheated bourbon which, as you may have surmised, means there’s wheat in the mashbill. In this case 18 percent, to go along with 68 percent corn and 14 malted barley. Wheat is less aggressive than rye, allowing more of the corn’s sweetness to take front and center. Also, in the flavor profile mix, raisins, cherries and wee bits of almond and toffee.

Buy Now: $94

Russell’s Reserve 1998

Russell’s Reserve Bourbon

Photo: Courtesy of Russell’s Reserve

In 1998, before master distiller Jimmy Russell’s 45th anniversary at Wild Turkey (and assumed retirement), his son Eddie set out to create a fitting tribute to his father’s legacy. Enter Russell’s Reserve 1998. Ole Jimmy can still be found at the distillery today, but his “retirement whiskey” is another story. Just over 2,000 bottles of this 102.2-proof bourbon were released in 2015 and sold out immediately. Of course, when it comes to running down impossible-to-find bottles, there’s always a guy who knows a guy who knows a guy . . . just be aware that that guy will want some serious coin for this collector’s item. As with most bourbon this mature, it’s woody and a tad dry. But Eddie made sure to halt the aging process in time to retain the vibrant caramel, vanilla, and fruity notes for which Wild Turkey is so famous. Of course he did—his dad wouldn’t have it any other way.

Buy Now: $2,000

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High Wire New Southern Revival Straight Bourbon made with Jimmy Red Corn

High Wire New Southern Revival Bourbon

Photo: Courtesy of High Wire Distilling Co.

Jimmy Red is a legendary moonshiner’s corn that had all but become extinct until a South Carolina farmer brought it back to life in the early aughts. By 2016 the folks at High Wire Distilling in Charleston, who felt that many of the “big boys” in the industry weren’t paying enough attention to the quality of corn used in the mash, were using Jimmy Red to make truly unique bourbon. The Jimmy Red Corn Straight Bourbon smells of nutmeg and toffee. The first sip is nutty, sweet, and mineralic. Swish it around a bit to unbind banana and butterscotch flavors. It boasts an extremely high oil content, yielding whiskey with an unusually creamy mouthfeel.

Buy Now: $109

Little Book Chapter 4: Lessons Honored

Little Book Chapter 4: “Lessons Honored”

Photo: courtesy Bounty Hunter Wine & Spirits

Freddie Noe is an eighth-generation distiller for the House of Beam, son of the brand’s current master distiller Fred Noe, and grandson of the late legend whiskey-maker, Booker Noe. Quite the pedigree, to be sure. Given that the Little Book series is Freddie’s first release, whiskey lovers are faced with a quandary—do they drink it or collect it? (Tip: buy two). Chapter 4: Lessons Honored is the latest in the collection, and it’s a blend of uncut, unfiltered whiskies: a four-year-old brown rice bourbon that offers oak and fruit; an eight-year-old “high rye” that adds spiciness that lingers into the blend’s finish; and a seven-year old bourbon Freddie calls “the anchor.” The finished product is soft and silky on the palate, giving way to that fiery ending. One of the finest whiskies in Beam’s expansive portfolio.

Buy Now: $175

High West American Prairie Bourbon

High West American Prairie

Photo: Courtesy of High West Whiskey

High West American Prairie is a blend of straight bourbons aged from two to 13 years. Rich and earthy on the palate, it reveals pleasant notes of candy corn, honey nougat and sweet corn bread biscuits, closing out with a flash of Granny Smith apple. Every purchase comes with a karmic boost, as well—High West donates 10 percent of profits from the sale of each bottle to the American Prairie Reserve, which is dedicated to protecting and preserving America’s natural resources.

Buy Now: $39

Knob Creek Limited Edition 2001

Knob Creek Bourbon

Photo: Courtesy of Knob Creek

Part of the first wave of so-called “small batch” bourbons that now command the market, Knob Creek was introduced in 1992 by the late great Jim Beam master distiller Booker Noe. Booker ran the show at Beam for more than 40 years and did yeoman’s work to help revitalize the flagging bourbon industry in the 1960s and ’70s. In 2001, Booker retired and was replaced by his son Fred. This limited-edition expression, released in 2016, marked that historic passing of the torch. Knob Creek Limited Edition 2001 was offered in five batches, each with robust oak and char notes balanced by sweet vanilla and warm brown spices. The finish is long, rich, and glowing.

Buy Now: $140

Double Eagle Very Rare Bourbon

bourbon Buffalo Trace

Courtesy of Buffalo Trace

The ornate crystal decanter is something to behold, but it’s what’s inside the bottle that makes this rare offering from the Buffalo Trace Distillery so special. The 20-year-old bourbon is matured twice as long as the standard Eagle Rare, and even after two decades, what emerged from the barrel is a surprisingly smooth and balanced 90-proof spirit. Hints of vanilla, toasted oak and caramel lead to a finish marked by tobacco and leather notes. Only 299 of these bottles were produced, so be prepared to pay top dollar on the secondary market. And be sure to insist on the individually numbered letter of authenticity included with each bottle sold.

Buy Now: $14,000


Mic.Drop Bourbon

Photo: Courtesy of PM Spirits

A delicious blend of 20 different casks of eight-year-old whiskey that offers multifarious flavors highlighted by maple syrup, coconut, cloves, and dark fruit. Mic.Drop. came out of nowhere in 2017 and now resides on the back bars of some of the country’s most prestigious drinking establishments. It’s easy to spot, too, with an eye-catching label designed by comic book artist Chris Batista. The follow up, Mic.Drop.2, was released in 2018 —140 bottles at $450 a pop.

Buy Now: $85

John E. Fitzgerald Very Special Reserve 20 Year Old

John E. Fitzgerald Bourbon

Photo: Courtesy of Heaven Hill

Whiskey lovers tend to speak of the old Stitzel-Weller Distillery in hushed, reverential tones. Before being shuttered in 1972, the facility produced brands such as Larceny, Old Fitzgerald, Pappy Van Winkle, and Weller’s Cabin Still. John E. Fitzgerald Very Special Reserve 20 Year Old contains wheated bourbon gleaned from 12 barrels produced at old Stitzel-Weller that had been designated for use in Old Fitzgerald. The John E. Fitzgerald Very Special Reserve offers a host of tastes that go great together, from cocoa to lemon to banana cream pie. The finish is lengthy and refined. A few years back, Heaven Hill released a miniscule amount of 375 mL bottles. They claim that’s all they had, yet there are whispers—hushed and reverential—that a secret supply still remains.

Buy Now: $1,800

Woodford Reserve Master’s Collection 2009 Seasoned Oak Finish

Woodford Reserve seasoned oak finish

Photo: Courtesy of Woodford Reserve

In the early 1800s, Woodford County Distillery owner Oscar Pepper and master distiller James Crow pioneered key bourbon-making processes such as sour mashing, copper pot distillation, and charred oak cask maturation. Woodford Reserve’s Master’s Collection ($129) is the belated thanks they get. Were either still around to sample this rich amber-colored delectation, surely they’d revel in the 2009 Seasoned Oak Finish’s robust oakiness and spice, as well as the keen notes of fruit jam, toasted almond, and dark chocolate. The homestretch lolls pleasantly, offering sweet butter and a hint of cool lemon custard. Be forewarned—finding a bottle is darn near a mission impossible.

Buy Now: $900

Jefferson’s Twin Oak Custom Barrel

Jefferson’s Reserve Bourbon

Photo: Courtesy of Jefferson’s Reserve

Founded in 1997, Jefferson’s is committed to crafting innovative small-batch blends, as evidenced by its slogan “alchemy is everything.” The brand is definitely onto something, and the 2018 release may well be its most ambitious whiskey yet. For six years Jefferson’s worked with the Independent Stave Company to develop a proprietary flash-charred barrel made with grooved staves that allows for maximum exposure to oak at the peak of flavor. The result is a well-balanced, mocha-tinged whiskey that coats the palate with sweet and spicy goodness. It has a medium-length finish with a touch of cedar and tart lemon.

Buy Now: $88

Parker’s Heritage Collection Cask Strength Kentucky Straight Bourbon Whiskey

Parker’s Heritage Collection Bourbon

Photo: Courtesy of Heaven Hill

This whiskey was created in tribute to Heaven Hill’s longtime master distiller, Parker Beam. Beam himself personally selected the barrels that were used for the Heritage Collection Cask Strength’s first edition, released in 2007. Beam, who passed away in January 2017, endeavored to make classic Kentucky bourbon. There’s no better example of stellar old-school hooch than this. It’s full-bodied, brimming with dried fruit flavor (figs and raisins) and possessing ample oak and tannins. Originally priced at $80, a bottle can now go for several thousand dollars on the secondary market.

Buy Now: $2,300

Maker’s 46

Maker’s Mark Bourbon

Photo: Courtesy of Maker's Mark

Maker’s Mark bottled its first run in 1958 under the distinctive dipped red wax seal that was the brainchild of founder Bill Samuels Sr.’s wife, Margie. They made one whiskey, one way. Then, in 2010, Maker’s released 46, its first new expression in 50 years. In bourbon circles, this was a seismic event, and more than a few skeptics were ready to pounce. Boy, did legendary distiller Bill Samuels Jr. ever rise to the challenge. He intensified the natural flavor notes of classic Maker’s—the vanilla, caramel, and spice—and created a more complex, richer-tasting bourbon with a creamier mouthfeel and lengthier finish. There’s no bitterness. It’s eminently approachable and easy to enjoy.

Buy Now: $44

Hudson Baby Bourbon

Hudson Baby Bourbon Whiskey

Photo: Courtesy of Tuthilltown Spirits

Introduced in 2006, Hudson Baby Bourbon is the first whiskey produced in New York since Prohibition and is the first commercially available bourbon ever to hail from the Empire State. Made with locally sourced corn at the Tuthilltown Spirits distillery in the Hudson Valley, the whiskey is aged in charred new American oak barrels, which imparts a strong, smoky wood quality. Beyond the char there’s a harmony of flavors, including vanilla toffee, pepper spice, and a bit of honey, raisin, and mint. It’s a eupeptic, buoyant whiskey that is easy to digest. It makes for an ideal maiden voyage for unseasoned adventurers.

Buy Now: $52

Willett Family Estate Bottled Bourbon

Willett Family Estate Bourbon

Photo: Courtesy of Willett Family Estate

Willett Family Estate Bottled Bourbon was introduced in 2008 as part of the family’s Private Barrel Selection program and was an immediate hit with the professional drinking class, which includes critics, bartenders and flat-out whiskey nuts. It’s an un-chill-filtered, barrel-proof, straight bourbon whiskey of unusual depth and complexity. Though it weighs in at a hefty 124.8 proof, Willett Family Estate Bottled Bourbon drinks surprisingly light. Pear, cocoa, and cherry are among the more prominent flavors. Bottles from the original release, which went for $100 at that time, go for thousands now, if you can find them.

Buy Now: $6,584

Savage & Cooke The Burning Chair Bourbon

The Burning Chair Bourbon from Savage & Cooke

Photo: Courtesy of Savage & Cooke

In 1998, when he was just 25, oenophilic phenom Dave Phinney founded Orin Swift Cellars and promptly turned it into a behemoth on the strength of powerful Zinfandel-driven wines such as The Prisoner. Today, at 46, Phinney is wowing the whiskey world with the Burning Chair, a bourbon produced at his newly built Savage and Cooke distillery on Mare Island in Vallejo, CA. Following a four-year fling with new American oak and a quickie inside barrels from Phinney’s Cabernet-based projects, the bourbon is titrated to 88 proof with pristine water from the Alexander Valley. What goes into the non-traditional black bottle is a lively spirit boasting an array of pleasantries including vanilla bean, maple and baked apple flavor. The initial sweetness gives way to the bite of citrus zest and barrel char, creating great balance and complexity. From one of the industry’s true iconoclasts, this is “boho booze” at its best.

Buy Now: $44

Michter’s 20 Year Kentucky Straight Bourbon

Michter’s 20 Year Kentucky Straight Bourbon

Photo: Courtesy of Michter's

When it comes to barrel aging, Michter’s master distiller Dan McKee and master of maturation Andrea Wilson consider 17 to 20 years to be the “fork in the road” point at which when certain barrels can achieve an extraordinary level of quality. The barrels McKee and Wilson selected for the 2019 edition of Michter’s 20 Year Kentucky Straight Bourbon were indeed something special, as the whiskey is nothing short of, well, masterful. This complex spirit is possessed of an array of cascading flavors including black cherry, honeysuckle and pecans. At 114.2 proof, it is not for those with tender tastes. This bourbon’s got brawn, yet it’s no brute. Yes its potency grabs your attention, but its composure is what leaves a lasting impression.

Buy Now: $5,021

Widow Jane “The Vaults” 2019

Widow Jane “The Vaults” 2019

Photo: Courtesy of Widow Jane

In September, Brooklyn-based distiller Widow Jane rolled out the first ever expression in a collection of planned annual releases of mature bourbons sourced from various facilities in flyover states. The Vaults 2019 is a marriage of 14-year and older Tennessee and Indiana whiskies selected by head distiller Lisa Wicker, who finished and blended the juice at the Widow Jane Rickhouse on Conover Street in Red Hook. So ya, the hip quotient is off the charts. Ah, but there’s plenty of substance to go with the style in a 99-proof powerhouse that smells of old baseball mitts and birch beer. Sip it and be seduced by its panoply of palate pleasers, from burnt BBQ ribs to vanilla ice cream, with some citrus zest and crème brulee crust to boot… and make it a Doc Marten’s boot (it is a Brooklyn whiskey, after all).

Buy Now: $241

Kentucky Owl Bourbon Batch #9

Kentucky Owl Bourbon Batch #9

Courtesy of Kentucky Owl Bourbon

In 1916, as the scourge of Prohibition loomed, the government seized a quarter of a million gallons of Kentucky Owl bourbon and put the company out of business. A century later, the Owl hoots again, resurrected by master blender Dixon Dedman, whose great-great-grandfather founded the brand back in 1879. Dedman avows that Batch #9 is the most robust expression he’s ever created, and the man isn’t kidding. It’s an absolute beast. Forget putting hair on your chest, this’ll give your tongue a bouffant ‘do. It’s made with four different distillates from four different mash bills, ranging in age from 6 to 14 years old. Nose brings syrupy sweetness with a hint of freshly mowed grass. The sweetness spreads across the mid-palate with thick viscous mouthfeel. Light spice on a well balanced finish.

Buy Now: $502

Old Rip Van Winkle 25 Year Old

Old Rip Van Winkle 25 Year Old

Photo: Dylan + Jeni Photographed at £10, Montage Beverly Hills

In February of 2017, the folks at the Buffalo Trace Distillery released 710 handmade glass decanters of Old Rip Van Winkle 25 Year Old at a suggested retail price of $1,800. It’s highly unlikely any of those bottles ever actually made it to a store shelf, and even less likely anyone procured a bottle for the sticker price. There are bottles available online on the secondary market; at this writing the going rate is around $14,000. It’s worth it if you got it. It’s what known as a wheated bourbon, which simply means wheat is the secondary grain in the mash bill (behind corn). Flavor wise, it’s softer and smoother than bourbons with more rye in the mash. It’s disarmingly delicate for a whiskey with so many years of aging under its belt.

Buy Now: $24,998

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