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

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

Knob Creek Bourbon Photo: Courtesy of Knob Creek

The end of the calendar year is nigh, and media outlets from The New York Times to Thrillist are marking the occasion by unleashing a torrent of “Best Of” lists. And we here at Robb Report are not above employing that well-worn journalistic trope as well. 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 decades. Over the last 21 years, incredible new American-made whiskies have come to market, from new and venerable producers alike. Here are 25 of the best bourbon releases since Y2K.

Heaven’s Door Bootleg Series Vol III

Heaven's Door Bootleg Volume III

Photo: courtesy Heaven's Door

When profiling a whiskey that gets its name from one of Bob Dylan’s most famous songs, the temptation to cleverly employ the legendary artist’s lyrics is hard to resist (wait for it…). Same can be said about the Heaven’s Door Bootleg Series Vol III itself. It’s a transcendent whiskey you’ll want to experience again and again. Bottled at cask strength after 13 years in barrel, with a bit of finishing in Vino de Naranja Casks, this just-released dram offers whiffs of peach and buttered popcorn, primes the palate with delightful cream soda, candied orange and animal cracker notes, and brings it home with some pepper and lemon zest. The Bootleg Series Vol III comes in handmade ceramic bottles emblazoned with one of Dylan’s classic paintings, Sunday Afternoon. Only 4,000 bottles have been made available, so keep your eyes wide, the chance won’t come again.

Buy Now: $545

Rabbit Hole Cavehill

Rabbit Hole Cavehill

Photo: courtesy Bounty Hunter Wine & Spirits

This four-grain wheated whiskey from the celebrated Louisville distillery’s core range is produced in small batches and boasts big flavor. There’s caramel, sweet corn, toasted grain and orange up front, followed by mint, ginger, black pepper and a dollop of maple syrup. It’s a bourbon that more than ably anchors a sour or an Old Fashioned, and makes for an estimable solo sipper as well. Finishes with a pleasant touch of vanilla and cinnamon.

Buy Now: $60

Booker’s Batch 2021-04 Noe Strangers Batch

Booker’s Batch 2021-04 ‘Noe Strangers Batch

Photo: courtesy Booker's

Legend has it that Jim Beam’s grandson, the late Booker Noe, first created his eponymous bourbon in 1988 as a holiday gift for his friends and family. Fortunately, the rest of us can now get in on the action. In 2021 the brand released four separate batches, and the 124.4-proof “Noe Strangers”—selected by Booker’s son and Beam’s seventh-generation master distiller Fred Noe—is the clear stand-out. Indeed, it’s an instant classic. Aged 6 years, 6 months, and 12 days (in new white oak barrels, of course), it offers vanilla and brown sugar on the nose, with plenty of sweetness on the palate. The initial heat is palpable, yet not overwhelming. Mouthfeel is delightfully creamy, the finish is long and warm. This robust, full-bodied whiskey is best enjoyed with a few drops of room temperature water to take some of the bite out of the beast.

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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: $3,500

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: $3,000

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 $549

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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Frey Ranch Single Barrel Straight Bourbon Whiskey

Frey Ranch Single Barrel Straight Bourbon Whiskey

Photo: courtesy Bitters & Bottles

Nevada’s Frey Ranch Distillery (pronounced “fray”) is one of only a handful of producers in the world to grow all of its grains sustainably on-site, and with good reason; the distillery is located smack-dab in the heart of the lush farming region of the Lake Tahoe watershed. The four-grain mash bill includes non-GMO corn, winter cereal rye, winter wheat and two-row barley. That fab four yields a tantalizing medley of flavors including dark chocolate, brown sugar, almond, honey and barrel char. At 130ish-proof, the whiskey comes on hot and heavy, but don’t let the high ABV scare you off—for a whiskey that packs so much wallop, the Frey Ranch Single Barrel is remarkably easy drinking.

Buy Now: $85

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: $459

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: $1,988

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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: $160

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: $16,000

Blue Run Kentucky Straight High Rye Bourbon Whiskey

Blue Run Kentucky Straight High Rye Bourbon Whiskey

Photo: courtesy Blue Run Kentucky Spirits

Blue Run Spirits has only been around since October 2020 but, boy, have they hit the ground running. Their 13.5-Year-Old Single Barrel Bourbon was crowned the Best Single Barrel Bourbon, 11 years and older at the 2021 San Francisco World Spirits Competition, and is worthy of inclusion here. But instead we’re giving the nod to the High Rye, as it’s the first Blue Run product with Bourbon Hall of Famer Jim Rutledge overseeing the production. Rutledge is a legend. Imagine owning a pair of Air Jordans personally designed by MJ, or Taylor Swift composing a song about YOUR devastating break-up. Blue Run High Rye Bourbon clocks in at 111 proof, and brims with baking spices, stone fruit and black pepper.

Buy Now: $150


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: $279

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: $2,300

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: $89

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: $1,000

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: $46

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: $5,000

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: $7,733

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: $373

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 six 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: $300

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.

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