The 50 Best Bourbons of the 21st Century (So Far)

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A lot of new bourbon has been released since the start of the 21st century, as the category has surged in popularity to reclaim, or even surpass, the standing it once had. That means there have been innovations in the world of this strictly defined style of whiskey, from new cask finishes to playing around with mashbills (always at least 51 percent corn by law), and even putting barrels into experimental warehouses to see how it affects the flavor. There have been some great successes, along with a few failures, but overall the past quarter century has been a boom time for bourbon.

We compiled a list of the most important bourbons released since 2000, including a few brands that were founded earlier but reached their pinnacle of success over the past 24 years and change. “Important” is a subjective term, but for this list it means bourbons that had some impact on consumers, the industry, or the general trajectory of the category. That means there might be some here that you don’t particularly care for, and that’s okay because even if a certain bourbon isn’t your favorite, it still might have made a mark on category.

I have been writing about bourbon, and other styles of whiskey, for a decade. During that time, I have tried hundreds of expressions from every major distillery in the U.S. along with many craft operations, and have gotten to sample bourbon from nearly every state with mashbills ranging from high-rye to low-rye to 100 percent corn. I also judge whiskey and other spirits for two competitions—the John Barleycorn Awards and New York World Wine and Spirits Competition—and write about spirits for numerous media outlets, so I’ve had a chance to hone my palate over the years.

I chose the bourbons on this list by considering a few factors. As explained before, the whiskey’s importance to the category played the biggest part, but quality, flavor, and availability were also taken into consideration. That being said, there are some bourbons on this list that are incredibly difficult to find, and extremely expensive if you do, but made the list because of the importance they have had. Take a look and see how many you’ve been able to try, and how many you should add to your whiskey wish list.

50. Thirteenth Colony Southern Bourbon Whiskey

50. Thirteenth Colony Southern Bourbon Whiskey
50. Thirteenth Colony Southern Bourbon Whiskey

There is a lot of great bourbon being made outside of Kentucky, and whiskey fans have taken particular note of Georgia’s Thirteenth Colony over the past few years. The bourbon is made from a mashbill of 70 percent corn and 21 percent rye, giving it a healthy dose of spice, and it is aged between four and six years. At 95 proof there’s a bit of heat on the palate, but that’s tempered by notes of baking spice, vanilla, and a bit of tannic leather.

Buy Now on Seelbach's: $45

49. Milam & Greene Very Small Batch

49. Milam & Greene Very Small Batch
49. Milam & Greene Very Small Batch

Heather Greene switched careers a few years ago—from whiskey expert and author to blender and distillery CEO (and still a whiskey expert)—and the whiskey world has been better off for it. Milam & Greene Very Small Batch is a blend of Kentucky and Tennessee bourbon that is finished with charred French oak staves and bottled at 108 proof. There have only been two batches released so far, and both have been fiercely good, really leaning into what Greene describes as jammy dark fruit notes on the palate.

Buy Now on Wine.com: $70

48. Wyoming Whiskey Small Batch Bourbon

48. Wyoming Whiskey Small Batch Bourbon
48. Wyoming Whiskey Small Batch Bourbon

The strength of this Wyoming distillery can be attributed in large part to the involvement of Steve Nally as master distiller, whose long whiskey career includes three decades at Maker’s Mark. He’s moved on, but this wheated bourbon remains strong, with a notable fruity character complemented by spice and vanilla notes. Scottish drinks company Edrington owns the distillery now, but the team continues to make the bourbon it set out to produce and has expanded the portfolio to include a variety of other whiskeys.

Buy Now on ReserveBar: $42

47. Woodinville Straight Bourbon

47. Woodinville Straight Bourbon
47. Woodinville Straight Bourbon

This Washington State craft distillery is now owned by Moet Hennessy, but it continues to make bourbon in small batches that can stand with anything produced by the legacy distilleries in Kentucky. The whiskey is shipped to the eastern part of the state to age, and the climate there does wonders to the liquid. There are several cask-finished expressions available, but start with the core bourbon to experience its creamy mouthfeel and complex palate full of classic bourbon notes.

Buy Now on ReserveBar: $36

46. Still Austin Bottled in Bond Red Corn Bourbon

46. Still Austin Bottled in Bond Red Corn Bourbon
46. Still Austin Bottled in Bond Red Corn Bourbon

Still Austin is a distillery located in the Texas capital making some extremely good craft whiskey that should really be on more people’s radars. It’s still a relatively small operation, and maybe that’s a good thing because it allows the team there to distill expressions like this excellent Red Corn Bourbon as part of its bottled-in-bond series. The mashbill includes nearly equal parts red and white corn, in addition to rye and barley, and the resulting bourbon is a superlative effort with notes of burnt marshmallow, vanilla pudding, spiced apple, and oaky smoke.

Buy Now on Total Wine & More: $80

45. Smooth Ambler Old Scout 7

45. Smooth Ambler Old Scout 7
45. Smooth Ambler Old Scout 7

This bourbon is produced by West Virginia distillery Smooth Ambler, which sources some of its whiskey (including this one) from MGP in Indiana. For a while the stocks had run low and the whiskey was not widely available, but it’s back now as a seven-year-old, high-rye (36 percent in the mashbill), non-chill filtered bourbon that hits all the right nots. At 99 proof, the flavor is bold and brash with notes of leather, tobacco, custard, and baking spices on the palate.

Buy Now Liquor Luxe: $76

44. Willett Pot Still Reserve

44. Willett Pot Still Reserve
44. Willett Pot Still Reserve

The Willett name has a long history in Kentucky bourbon, but the current distillery has only been making whiskey for a little more than a decade. The Pot Still Reserve expression, first introduced in 2008, is instantly recognizable for its bottle shaped like the titular still, and can be a polarizing one for bourbon fans. In the early years the bourbon was sourced, and many people thought those bottlings were better than the younger liquid produced in-house that gradually replaced it. Try to find one of both to compare, but be prepared to pay a lot on the secondary market.

43. Wild Turkey 101

43. Wild Turkey 101
43. Wild Turkey 101

This bourbon could not be left off this list, and not just because the label got a redesign in 2022. We’ve discussed Master’s Keep and Rare Breed, but this affordable and dependable workhorse of a bourbon is one of the best that you can find, and that has remained true over the past quarter century. There’s an 81-proof version as well, but really why bother? Wild Turkey 101 never fails to deliver with its signature nutty, grainy, vanilla, pepper flavor profile that has made it an icon of bourbon, and pop culture, for a reason.

Buy Now on ReserveBar: $28

42. Rabbit Hole Mizunara Founder’s Collection

42. Rabbit Hole Mizunara Founder’s Collection
42. Rabbit Hole Mizunara Founder’s Collection

Rabbit Hole, located in downtown Louisville, both sources and distills its own whiskey. The core expression is a four-grain bourbon, but the distillery also has the high-end, limited-edition Founder’s Collection that is made up of other styles of whiskey. The barrels used for this come from founder Kaveh Zamanian’s private stocks, and the best release so far is the Mizunara expression. The second release of this whiskey is a 15-year-old bourbon finished in Japanese oak for almost a year, resulting in a chocolate and caramel coated spice bomb of a whiskey.

Buy Now on Frootbat: $2,051

41. Laws Whiskey House Four Grain Bottled in Bond Bourbon

41. Laws Whiskey House Four Grain Bottled in Bond Bourbon
41. Laws Whiskey House Four Grain Bottled in Bond Bourbon

Laws is a Colorado distillery that has been releasing increasingly older expressions of its bottled-in-bond bourbon. The whiskey is made from a four-grain mashbill that includes heirloom wheat, rye, and malted barley, in addition to corn. The most recent expression was eight years old, which is well beyond the four years required by the BIB designation. There are distinctive fruit and licorice notes to this bourbon, which is another reason to seek it out.

Buy Now on Laws Whiskey House: $85

40. Kentucky Owl Batch 12

40. Kentucky Owl Batch 12
40. Kentucky Owl Batch 12

Dixon Dedman revived his family brand and turned it into a cult whiskey success story, releasing batches of sourced bourbon that sell for hundreds of dollars per bottle. He’s since moved on, and Stoli now owns the brand (and is building a distillery), but the batches of bourbon keep coming and are still very good under the watchful eye of master blender John Rhea. The 12th batch combined bourbon aged four to 14 years, a creamy butterscotch candy of a whiskey that fired on all cylinders.

Buy Now on Caskers: $322

39. Hillrock Estate Solera Aged Bourbon

39. Hillrock Estate Solera Aged Bourbon
39. Hillrock Estate Solera Aged Bourbon

Travel a few hours north of New York City to the Hudson Valley and you’ll find Hillock Estate, a grain-to-glass distillery that is making high-end bourbon, rye, and malt whiskey. The bourbon is quite good, aged in a solera-style system that incorporates older liquid into the blend before being finished in 20-year-old Oloroso sherry casks. There is a lot of craft bourbon from outside of Kentucky to try, and this is one of the better examples of that category.

Buy Now on Wine.com: $105

38. Remus Gatsby Reserve

38. Remus Gatsby Reserve
38. Remus Gatsby Reserve

MGP makes whiskey for many different brands, including Dickel, Smooth Ambler, and Bulleit. But it also has its own lineup named after the notorious bootlegger George Remus. The pinnacle expression is the annual release of Remus Gatsby Reserve, a 15-year-old bourbon that is decadent and delicious, with equal parts sweetness, spice, and tannic oak that doesn’t overwhelm notes of fruit and black pepper.

Buy Now on ReserveBar: $300

37. Henry McKenna Single Barrel

37. Henry McKenna Single Barrel
37. Henry McKenna Single Barrel

At 10-years-old, this bottled-in-bond bourbon from Kentucky distillery Heaven Hill sits in the sweet spot of maturation. It’s a single-barrel expression, so every bottle will be slightly different depending on which cask it came from. Still, it’s a uniformly respected bourbon that has increased in price as its popularity has grown, with a palate that is classic bourbon—notes of vanilla, spice, blackberries, and caramelized brown sugar on every sip.

Buy Now on Caskers: $73

36. Heaven’s Door Redbreast Master Blenders’ Edition

36. Heaven’s Door Redbreast Master Blenders’ Edition
36. Heaven’s Door Redbreast Master Blenders’ Edition

It makes sense to be a little dubious about a celebrity spirit, but Bob Dylan’s Heaven’s Door whiskey is the real deal. The brand took over a Kentucky distillery last year, but for years the company sourced bourbon and rye from distilleries in Tennessee and Indiana, sometimes finishing the whiskey in different types of barrels. That is the case with this fantastic entry in the Master Blenders’ series, a 10-year-old bourbon finished in Redbreast single pot still Irish whiskey casks for 15 months. It’s a great meeting of whiskey worlds, and a cask finish that truly works.

Buy Now on Cana Wine Co: $349

35. Garrison Brothers Guadalupe

35. Garrison Brothers Guadalupe
35. Garrison Brothers Guadalupe

Texas bourbon is booming, and Garrison Brothers is one of the main reasons why. This distillery about an hour outside of Austin was the first to legally make whiskey in the state since Prohibition when it was founded in 2005, although nowadays it has some fierce competition. The wheated bourbon made there is not for everyone—the intense climate and use of some small barrels to mature the whiskey really gives it a concentrated oaky flavor. But this is big, bold Texas bourbon, and the Guadalupe expression in particular, stands out due its two-year secondary maturation in port casks which adds fruity tannic notes to the mix.

Buy Now on ReserveBar: $225

34. Frey Ranch Bourbon

34. Frey Ranch Bourbon
34. Frey Ranch Bourbon

Out in the Nevada desert, the husband-wife team that runs the Frey Ranch distillery is making whiskey using a true grain-to-glass model. The distillery’s bourbon is made from a four-grain mashbill that incorporates winter wheat into the recipe, giving this well-aged whiskey a balanced palate of baking spice, sweet vanilla, oaky char, and stone fruit notes. Give the single barrel expression a try to see how it differs depending on the cask, but the flagship bourbon is a fantastic newcomer onto the ever-growing whiskey scene.

Buy Now on ReserveBar: $58

33. Balcones Texas Pot Still Bourbon

33. Balcones Texas Pot Still Bourbon
33. Balcones Texas Pot Still Bourbon

Waco, Texas distillery Balcones has had a busy few years. Diageo acquired it in 2022, adding the outfit to its other American whiskey brands like Bulleit and IW Harper, but fortunately things haven’t seemed to change much as far as production and experimentation. The bourbon is distilled in copper pot stills instead of the usual column still, and aged in casks that are charred and toasted to various levels. The result is a fruity, full-bodied bourbon that is a bit on the young side but still full of flavor, an important addition to Texas bourbon and the category overall.

Buy Now on ReserveBar: $38

32. Chattanooga Whiskey 91 Tennessee High Malt

32. Chattanooga Whiskey 91 Tennessee High Malt
32. Chattanooga Whiskey 91 Tennessee High Malt

Chattanooga has been making a big impact on Tennessee whiskey, and the American scene overall, since its founding in 2011. The distillery released its first in-house produced bourbon about six years later, a four-grain whiskey made from a mashbill of corn, malted rye, and three kinds of malted barley that is finished in a solera barrel. The result is a unique bourbon with a strong malted chocolate character on the palate that really stands out from the pack.

Buy Now on ReserveBar: $35

31. Old Grand-Dad 114

31. Old Grand-Dad 114
31. Old Grand-Dad 114

Old Grand-Dad is a brand owned by Beam Suntory (now known as Suntory Global Spirits) produced at the home of Jim Beam, the James B. Beam Distilling Co. This is a proudly humble and underrated bourbon made from the same high-rye mashbill as Basil Hayden, but there are many whiskey fans who believe that it’s the superior product. This is why it Old Grand-Dad is still relevant and important–it is still a whiskey to hunt down for those in the know, even as the Basil Hayden brand portfolio has been given shiny new expressions over the past few years. If you can find a bottle of the 114 proof expression, grab it—it far surpasses the regular 80 proof in terms of flavor, and it remains a fairly inexpensive whiskey.

Buy Now on Caskers: $34

30. Barrell Armida

30. Barrell Armida
30. Barrell Armida

Barrell Craft Spirits is a Kentucky whiskey company that is singularly focused on blending, and over the past decade it has proven to be one of the best in the game. This Louisville operation carefully sources barrels from distilleries in states like Indiana, Tennessee, and of course Kentucky, and sometimes gives the whiskey really interesting secondary maturations or cask finishes. Such is the case with Armida, a limited-release blend of bourbon from three different states separately finished in pear brandy, rum, and Sicilian amaro casks—likely a combination you’ve never had before, but one that you should definitely try.

Buy Now on ReserveBar: $80

29. Bardstown Bourbon Company Phifer Pavitt Reserve

29. Bardstown Bourbon Company Phifer Pavitt Reserve
29. Bardstown Bourbon Company Phifer Pavitt Reserve

Bardstown Bourbon Company is one of the best new distilleries in Bardstown, the small enclave at the epicenter of Kentucky bourbon. BBC does it all: sources, contract distills for other brands, and releases its own whiskeys. This whiskey, part of Bardstown’s Collaborative Series, is a 10-year-old sourced Tennessee bourbon that was finished for 18 months in Cabernet barrels from the Phifer Pavitt winery in Napa. The second edition of this collaboration came out in 2021, and is one of the best examples you can find of a wine finish with notes of juicy berry, black pepper, and dried fig in every sip.

Buy Now on Frootbat: $920

28. Old Forester Birthday Bourbon 2021

28. Old Forester Birthday Bourbon 2021
28. Old Forester Birthday Bourbon 2021

Birthday Bourbon is an annual release from Kentucky distillery Old Forester that gets nearly as much attention as Pappy Van Winkle and the Buffalo Trace Antique Collection, and for good reason. The whiskey was first released in 2002 to commemorate Old Forester founder George Garvin Brown’s September 2 birthday. Each release since then varies in terms of age and proof, but the 2021 expression was a standout—a 12-year-old bourbon bottled at 104 proof with notes of cherry, caramel, and peach syrup on that palate that gave it an almost Cognac-like character.

Buy Now on Flaviar: $1,000

27. Wild Turkey Rare Breed

27. Wild Turkey Rare Breed
27. Wild Turkey Rare Breed

Wild Turkey is best known for its affordable and dependable 101-proof bourbon, a whiskey that should be a staple of any home bar. But the distillery’s barrel-proof Rare Breed expression stands with the best of this category of whiskey that isn’t diluted before bottling. The whiskey launched before the turn of the century, but it has been important over the past 24 years as the barrel-proof market has expanded–Rare Breed is not as high in proof as others like Elijah Craig Barrel Proof or Booker’s, but that’s a good thing because the Wild Turkey character shines through without blowing out your palate, revealing notes of toasted nuts, dried fruit, and vanilla spice.

Buy Now on ReserveBar: $69

26. Pinhook Vertical Series Bourbon

26. Pinhook Vertical Series Bourbon
26. Pinhook Vertical Series Bourbon

Pinhook is a whiskey company that names its expressions after racehorses, but that’s not the most interesting thing about it. That honor goes to its Vertical Series, which follows a whiskey as it ages by releasing an annual vintage starting at four years old and eventually culminating in a 12-year-old version. The bourbon in this series was distilled at MGP in Indiana, and it is fascinating to taste the different vintages side by side to see how they compare. The 2024 expression, a nine-year-old bourbon, comes out soon.

Buy Now on ReserveBar: $120

25. Eagle Rare 25

25. Eagle Rare 25
25. Eagle Rare 25

This is the oldest bourbon ever released from Buffalo Trace’s Eagle Rare brand. The secret to its success is that it spent its final five years aging in the distillery’s experimental Warehouse P, where temperature and humidity are carefully controlled. While the palate veers towards the dusty oak end of the spectrum, there’s a nice complexity to this whiskey with notes of menthol, pepper, peanut butter crunch, and a touch of tannic bitterness.

Buy Now on Bourbon Barrel Blend: $8,835

24. Dickel Bourbon

24. Dickel Bourbon
24. Dickel Bourbon

George Dickel is the second best known Tennessee whiskey brand after the ubiquitous Jack Daniel’s, but Nicole Austin, director of George Dickel and luxury North American whiskey, is doing her best to change that with a range of new expressions that are consistently excellent. One of these is Dickel Bourbon, an eight-year-old whiskey made in the same way as regular Dickel, only with a flavor profile that Austin felt was more befitting of the name bourbon. Sip it or mix it, this is a Tennessee bourbon that should be on your bar cart.

Buy Now on Caskers: $26

23. Larceny Bourbon

23. Larceny Bourbon
23. Larceny Bourbon

Heaven Hill is perhaps better known for its other bourbon brands like Evan Williams and Elijah Craig, but over the years the distillery’s wheated bourbon, Larceny, has been getting renewed (and deserved) attention. This whiskey is made with wheat as the flavoring grain in the mashbill instead of rye, and as you might expect it has a sweeter flavor profile. A barrel-proof version joined the lineup a few years ago, but if you haven’t tried the regular 92-proof version it’s not too late to start now.

Buy Now on BOunty Hunter Wine & SPirits: $25

22. Parker’s Heritage Collection 16th Edition Double Barreled Blend

22. Parker’s Heritage Collection 16th Edition Double Barreled Blend
22. Parker’s Heritage Collection 16th Edition Double Barreled Blend

This 2022 bourbon was the 16th release in Heaven Hill’s Parker’s Heritage Collection, a series of whiskeys meant to celebrate the legacy of the late master distiller Parker Beam. Each release highlights a different mashbill and maturation method, and this expression was a blend of double-barreled 13-year-old bourbon and 15-year-old bourbon. The former comprises about two-thirds of the blend and makes this whiskey sing with deep notes of char, vanilla, stone fruit, and a smoky wisp on the finish.

Buy Now on Caskers: $1,022

21. Kings County Straight Bourbon

21. Kings County Straight Bourbon
21. Kings County Straight Bourbon

Brooklyn distillery Kings County jumpstarted the whiskey movement in New York City when it opened more than a decade ago, making it the first distillery to legally operate in the Big Apple since Prohibition. The core straight bourbon is made from a mashbill of 80 percent corn and 20 percent malted barley, with no rye in the recipe. It’s aged from three to six years in a variety of barrel sizes, yielding a slightly woody and sweet bourbon that is a favorite of craft connoisseurs and bourbon fans around the country.

Buy Now on Caskers: $76

20. Knob Creek 9 Year Bourbon

20. Knob Creek 9 Year Bourbon
20. Knob Creek 9 Year Bourbon

In 2020, Knob Creek got its nine-year-old age statement back after an absence of a few years, which renewed the importance of this classic bourbon. This was a good thing, because at nearly a decade old this Jim Beam Small Batch Collection expression is a well-aged and good-value bourbon that is always a solid sipper. Knob Creek, a brand that has been around since the early 1990s, is bottled at 100 proof, making it perfect for using in cocktails or sipping on its own. Give this a try in an Old Fashioned or any classic cocktail, you won’t be disappointed.

Buy Now on Caskers: $37

19. W.L. Weller 12 Year

19. W.L. Weller 12 Year
19. W.L. Weller 12 Year

This is another Buffalo Trace bourbon that has become increasingly hard to find over the years. That can be blamed on people figuring out that this bourbon’s wheated mashbill is the same as that of Pappy Van Winkle (there are other differences between how the two brands are produced, however), but with wider availability and lower prices. The 12-year-old expression is now a collector’s item, and you’ll usually see it being sold for hundreds of dollars online. But the soft brown sugar sweetness and caramel candy notes that define this whiskey’s palate reveal that there’s actually something behind the hype.

Buy Now on ReserveBar: $286

18. Heaven Hill Bottled-in-Bond

18. Heaven Hill Bottled-in-Bond
18. Heaven Hill Bottled-in-Bond

Heaven Hill’s Bottled-In-Bond bourbon used to be one of the best bangs for your buck—an affordable but high-quality whiskey that those in the know would seek out. The distillery refreshed the liquid a little white back, upping the age to seven years old and giving the bottle and label a complete makeover. Of course, the price went up as well, but that shouldn’t overshadow the fact that this is still a fantastic bourbon that can be sipped on its own or used in any cocktail you can think of.

Buy Now on ReserveBar: $55

17. Blanton’s Original Single Barrel

17. Blanton’s Original Single Barrel
17. Blanton’s Original Single Barrel

Single-barrel bourbon is pretty common these days, but it wasn’t always that way. Blanton’s is known as the “original single barrel,” and that is indeed the case. In 1984, Elmer T. Lee, master distiller at the George T. Stagg Distillery (now known as Buffalo Trace), launched Blanton’s as the first commercially available single-barrel bourbon. Blanton’s has come a long way since those early days, becoming a bonafide collector’s whiskey over the past quarter century. There are now a few different versions of the bourbon, including Gold, Straight From the Barrel, and the 80-proof international product Blanton’s Special Reserve, but we keep coming back to the original.

Buy Now on ReserveBar: $157

16. New Riff Bottled in Bond Bourbon

16. New Riff Bottled in Bond Bourbon
16. New Riff Bottled in Bond Bourbon

New Riff has made a name for itself by doing one thing really well: releasing high-quality bottled-in-bond whiskey. The distillery actually has some more experimental expressions that are worth trying as well, but the core bourbon (and rye) has always met the BIB requirements—at least four years old, exactly 100 proof, and produced at one distillery—so there’s never been a green, immature batch in the mix. Try this bourbon for yourself and note the ripe berry, brown sugar, and caramel notes that grace every sip.

Buy Now on Frootbat: $49

15. Old Forester 1920 Prohibition Style

15. Old Forester 1920 Prohibition Style
15. Old Forester 1920 Prohibition Style

Old Forester, owned by drinks giant Brown-Forman, is a name that is practically synonymous with bourbon. The distillery is known for its inexpensive whiskeys, but it has added many higher-end release to its lineup over the years. One of the standouts is 1920 Prohibition Style, an homage to the period when Old Forester was making whiskey under a medicinal license. This is a strong bourbon at 115 proof, but the classic Old Forester character shines through with a burst of maple syrup, cinnamon spice, and s’mores on the palate.

Buy Now on ReserveBar: $61

14. Russell’s Reserve 13 Year Old Bourbon

14. Russell’s Reserve 13 Year Old Bourbon
14. Russell’s Reserve 13 Year Old Bourbon

Russell’s Reserve is the small batch brand extension from Kentucky’s Wild Turkey distillery. The whiskey really stands out for its high quality, not to mention the affordability of its core 10-year-old bourbon. But a few years ago, Russell’s released an older 13-year-old expression that immediately became a cult whiskey hit, and for good reason. These days, this hard-to-find bourbon commands high prices on the secondary market, but the rich chocolate, nut, caramel, and leather notes make it well worth the expense.

Buy Now on Frootbat: $400

13. Pappy Van Winkle 15 Year

13. Pappy Van Winkle 15 Year
13. Pappy Van Winkle 15 Year

What more is there to say about Pappy? This cult bourbon exploded in popularity more than a decade ago and its age statement expressions, ranging from 10 to 23 years old, sell for thousands of dollars on the secondary market. The fact is that this wheated bourbon, which is made by the Van Winkle family in partnership with Buffalo Trace, is very good, particularly the younger expressions (it tends to veer towards the tannic side over 20 years, as any bourbon would). The 15-year-old stands out, teetering on the edge of becoming overly oaky but pulling back just in time with rich notes of leather, tobacco, vanilla, and brown sugar.

Buy Now on Caskers: $1,835

12. Woodford Reserve Double Oaked

12. Woodford Reserve Double Oaked
12. Woodford Reserve Double Oaked

Brown-Forman’s Woodford Reserve distillery, which opened in the 1990s, really helped to jumpstart the premium bourbon category. For years, master distiller Chris Morris was in charge of making this whiskey meet all the elements of his flavor wheel, with notes of vanilla, citrus, spice, and brown sugar coating the palate. Elizabeth McCall now helms the operation and the bourbon remains a favorite of many whiskey fans, with a complexity that calls for sipping neat and a proof that’s high enough to work in cocktails. The Double Oaked expression arrived in 2012, at a time when finishing a bourbon in a secondary batch of new charred oak barrels was unusual. But the extra burst of flavor it gives this whiskey was a great success, and paved the way for others.

Buy Now on Caskers: $54

11. E.H. Taylor Small Batch

11. E.H. Taylor Small Batch
11. E.H. Taylor Small Batch

This bourbon was named after the man who was behind the Bottled-in-Bond Act of of 1897, so of course it follows those strict regulations—the whiskey is at least four years old, bottled at 100 proof, and the product of one distillery and one distillation season. While “small batch” has no real meaning, presumably E.H. Taylor is produced in smaller volumes than other Buffalo Trace bourbons. The bottom line is that this has become a highly coveted whiskey since it was first released more than a decade ago due to its rich flavor and balance of spice and sweetness.

Buy Now on Caskers: $125

10. Michter’s 25

10. Michter’s 25
10. Michter’s 25

Michter’s core lineup of bourbon, rye, and American whiskey is excellent, but some of the older age statement expressions from this Kentucky distillery really stand out—not usually the case in the American whiskey category, which can become overly oaky as it matures. Michter’s 25-year-old bourbon is selected from carefully sourced barrels that truly show how a bourbon this old can still be complex, nuanced, and not overly tannic. This is a very expensive bottle, but one that is worth tasting at some point in your whiskey journey if you have the chance.

Buy Now $9,090

9. Maker’s Mark Cask Strength

9. Maker’s Mark Cask Strength
9. Maker’s Mark Cask Strength

The past few years have seen some notable additions to the Maker’s Mark lineup, including various wood stave finishes and the phenomenal Cellar Aged, which is the oldest bourbon to date released by the distillery. But the Cask Strength version is the best expression to join the Maker’s family, a high-ABV but not high-octane version of the core wheated bourbon. It’s sweet but not cloying, smooth but never boring, and drinks exactly the way you want a classic barrel-proof bourbon to.

Buy Now on ReserveBar: $70

8. Bulleit 10 Year Bourbon

8. Bulleit 10 Year Bourbon
8. Bulleit 10 Year Bourbon

Bulleit has been making whiskey at its Kentucky distillery for a few years now, but the Diageo-owned brand has yet to release any of its own juice. In the meantime, Bulleit continues to source its Kentucky bourbon, made using a high-rye mashbill, from other distilleries. This bourbon is popular for a reason—at 90 proof there’s some kick and heft to the palate, but it’s still an easy drinker with a nice balance of sweetness and black pepper spice. The 10-year-old expression was first released in 2013, a welcome brand extension that ups the notes of oak, fruit, and caramel, and is very reasonably priced compared to some other whiskeys this old.

Buy Now on Bounty Hunter Wine & Spirits: $50

7. Jefferson’s Ocean Aged at Sea

7. Jefferson’s Ocean Aged at Sea
7. Jefferson’s Ocean Aged at Sea

There are a lot of bourbons to choose from the Jefferson’s lineup, but probably the most notable and unique expression is Ocean Aged at Sea. Some people call it a gimmick, but this whiskey travels the world on a container ship while maturing in barrels where it is subjected to different temperatures and humidity along the way that accelerate the interaction between wood and whiskey. The result of this extended maritime journey is a deeply flavorful bourbon with notes of cinnamon, brown sugar, and dark roasted coffee.

Buy Now on ReserveBar: $77

6. George T. Stagg 2023

6. George T. Stagg 2023
6. George T. Stagg 2023

George T. Stagg is a member of the Buffalo Trace Antique Collection, a series of whiskeys released once a year that become instant collector’s items. The last release of this barrel-proof, uncut, and unfiltered bourbon was an assertive 135 proof, which is approaching hazmat whiskey levels. This 15-year-old bourbon was somehow still very drinkable, although a little bit of water or a large ice cube is a good way to go while still revealing deep notes of oak, spice, vanilla, and dark stone fruit.

Buy Now on Frootbat: $1,000

5. Wild Turkey Master’s Keep Voyage

5. Wild Turkey Master’s Keep Voyage
5. Wild Turkey Master’s Keep Voyage

Eddie Russell, the son of the legendary Wild Turkey master distiller Jimmy Russell, is the man responsible for the Master’s Keep series from Wild Turkey. The younger Russell experiments with the whiskey in ways his father wouldn’t be interested in—case in point is this 10-year-old bourbon finished in rum casks sourced from Appleton Estate. This is one of the best cask-finished bourbons of the 21st century, an artful blend of complementary flavors that stands with the best.

Buy Now on Frootbat: $380

4. Angel’s Envy Port Finish

4. Angel’s Envy Port Finish
4. Angel’s Envy Port Finish

Nearly every bourbon brand has a cask-finished expression in its lineup these days, meaning a whiskey that spent time in another barrel after initially being aged in new charred oak. Angel’s Envy was at the forefront of this trend in American whiskey—every bottle of the Downtown Louisville distillery’s bourbon gets a secondary maturation of up to six months in port casks imported from Portugal. That gives this bourbon rich notes of dark berries and dried fruit, along with a sprinkling of baking spices to round out the palate.

Buy Now on ReserveBar: $44

3. Four Roses Single Barrel

3. Four Roses Single Barrel
3. Four Roses Single Barrel

Four Roses has a long whiskey history, but it wasn’t until 2002 that the distillery renewed its focus on making high-quality Kentucky straight bourbon for the U.S. market. Ten different bourbons using two mash bills and five different yeast strains are made at the distillery. The core bourbon combines all of these recipes, but you can also buy a single barrel expression that features just one. This whiskey is aged for seven to nine years and bottled at 100 proof, and while the flavor changes depending which barrel it comes from, it is a consistently delicious whiskey that is one of the best single barrel expressions you can find.

Buy Now on ReserveBar: $48

2. Elijah Craig Barrel Proof

2. Elijah Craig Barrel Proof
2. Elijah Craig Barrel Proof

Heaven Hill’s barrel-proof version of its core Elijah Craig bourbon, which was first released in 2013, comes out in three batches per year, each one differing in proof and age. This is consistently one of the best barrel-proof bourbons that you can find, with the ABV ranging somewhere between 60 and 65 percent. Sip this whiskey neat, over some ice, or even use it in a cocktail—Elijah Craig Barrel Proof is surprisingly versatile despite its strength.

Buy Now on ReserveBar: $83

1. Booker’s 30th Anniversary Bourbon

1. Booker’s 30th Anniversary Bourbon
1. Booker’s 30th Anniversary Bourbon

Booker’s is the original barrel-proof expression in the Jim Beam Small Batch Collection created by the late legendary master distiller Booker Noe. It comes out four times per year, with each release varying in proof and age and a different backstory and name, but it usually clocks in around six to seven years old and between 120 and 130 proof. The special 30th Anniversary Bourbon came out in 2018, and became an instant collector’s item. This is Booker’s for the hardcore Booker’s fans—a blend of nine and 16-year-old whiskey at 125.8 proof that is full of caramel, spice, heat, and funky wood notes.

Buy Now at the Barrel Tap: $1,200

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