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The Best Bottles Of Bourbon Between $300-$500

Spending a car payment on a bottle of bourbon is a great big swing. But with serious money comes some pretty serious whiskey. Booze in the $300-$500 range represents an investment in your own bourbon journey. It means you’re looking for something truly unique, because that’s definitely what you get at this price point.

It should go without saying, these prices are not for beginners or anyone just dipping a toe into the broader bourbon world. These whiskeys are the ones you hunt down, cherish, and break out when something truly spectacular happens in your life. Or maybe you store one of these expressions in a vault and sell it down the road for a tidy return. (Option three is that you have unlimited means and none of this caveating matters — in that case, PLEASE SHARE.)

All that being said, we’re not in quadruple digits… yet (we’ll get there). So consider these 10 bourbon whiskey picks to be fairly accessible, compared to what’s to come. Still, we’re clearly getting deep into collector’s item territory with special one-offs and hard-to-find limited releases that we may never see again. That makes this step in our “bourbon at every price point” project a whole lot of fun.

Angel’s Envy Cask Strength

Bacardi

ABV: 60.2%

Average Price: $318

The Whiskey:

This whiskey from Angel’s Envy is much beloved and lauded. It’s been called the “best spirit in the world” before, which brings a lot of preconceived notions to this bourbon. The story behind the bottle is a classic tale of sourced whiskey barrels treated exactly right once picked.

The blend of hand-chosen barrels are finished in port casks like the majority of the much-loved Angel’s Envy bourbon line, then bottled with no cutting or fussing.

Tasting Notes:

Based on the 2020 limited release, you’re going to get a nose full of fruits — spicy stewed plums, ripe apricots, and tart cherry — next to a well-aged balance of worn library leather-bound books, ashy wood, and a sugar-maple cookie with a good punch of vanilla. The taste really holds onto the cherry while adding in a salted caramel vibe next to bitter dark chocolate all housed in a cedar box that was once the home to rich tobacco leaves. The end brightens up with a burst of orange zest next to that tobacco and cedar as the finish takes its sweet time fading away.

Bottom Line:

You get a clear sense of “classic” old bourbon notes with a pretty big alcohol kick. For this price, what you’re really paying for is the expertise of Angel’s Envy team finding truly special barrels and presenting that experience in the glass.

Old Forester 150th Anniversary Batch Proof

Brown-Forman

ABV: 62.8%

Average Price: $322

The Whiskey:

This special release from Old Forester celebrates 150 years of whiskey making by the brand with “150” at the core of the line. Master Taster Jackie Zykan created three batches of this limited release from 150 barrels that were specifically selected by Master Distiller Chris Morris. Once these bottles are gone, there won’t be a whiskey like this from Old Forester again.

Tasting Notes:

Based on Batch no. 1, you’ll be greeted with a mingling of menthol and anise with rich and buttery caramel next to a hint of holiday spices and a touch of sweet fruit. The palate embraces the holiday spice and adds in a peppery edge while the sweetness leans towards pancake syrup with a hint of dark chocolate and old wood beams lurking in the background. The finish marries the dark chocolate to the almost chili pepper spice on the medium-length finish as flourishes of orange oils, wet leather, and salted caramel kettle corn linger on your nicely warmed senses.

Bottom Line:

This is pretty much a collector’s item at this point. It was a special release from a special barrel selection that we’re just not going to see again. That being said, the price is only double its original MSRP, meaning you won’t feel too terrible if you do crack it open to celebrate something.

Kentucky Owl Bourbon

Stoli Group

ABV: 63.8%

Average Price: $350

The Whiskey:

Kentucky Owl was Dixon Dedman’s baby. The sourced bourbon is based all around Dedman’s masterful blending skills and his uncanny ability to choose the best barrels for this brand. Sadly, Dedman has left Kentucky Owl to find new avenues to bring the masses great bourbon, but his blends live on and can still be found on the shelf (for now).

Tasting Notes:

Based on the last release, Batch no. 9, expect an opening of apple fritters with maple caramel candies next to vanilla husks and a touch of woody tobacco spice. The palate adds some peppery spice to the caramel while a steaming mug of black tea cut with floral honey warms you down to your soul. The vanilla and honey become creamy as shots of orange oils cut through on the finish, leaving you buzzing from an almost … grape tobacco vibe.

Bottom Line:

There’s certainly going to be a “Dixon Kentucky Owl” and a “Not Dixon Kentucky Owl” divide for bourbon collectors (and drinkers) starting with whatever the next release is. So grab the bottles you can now if you want to taste a true master at work when it comes to sourcing and blending.

Parker’s Heritage Heavy Char Barrels Aged 10 Years

Heaven Hill

ABV: 60%

Average Price: $392

The Whiskey:

Every year, Heaven Hill releases their special Parker’s Heritage whiskey and it’s always a barn burner. Last year’s release was a 10-year-old bourbon aged in very heavily charred oak. The whiskey was rested for ten long years in 102 barrels in a very specific part of a specific warehouse at Heaven Hill to imbue the spirit with that x-factor.

Tasting Notes:

Now, you’ll probably hear “heavily charred” and “ten long years” and think this is going to be some big, woody, charcoal-filled, and overdone whiskey. It’s the opposite of that and you learn that from the first nose of subtle orchard fruits stewing in holiday spices, vanilla, and buttery brown sugars. The citrus comes in early with a deep orange marmalade feel next to a buttery Southern biscuit cut with some dried fruits, eggnog spices, and… maybe unsalted nuts.

The end holds onto the spice while keeping the fruity sweetness front-and-center on the slow fade.

Bottom Line:

This is the 14th release in Parker’s Heritage line and one of our favorites from the list. Though, it’s still hard to forget about 2018’s Orange Curaçao Finish Bourbon. If you can’t get that classic, this is also excellently crafted bourbon from one of the true powerhouses of Kentucky bourbon.

Four Roses 130th Anniversary

Kirin Brewery

ABV: 54.2%

Average Price: $399

The Whiskey:

This 2018 special release from Four Roses had a very limited run, meaning there aren’t a lot of bottles left out there. The juice in the bottle is a blend of four whiskey recipes (generally all high-rye) from Four Roses that were aged from ten to 16 years before coming together for this one-off.

Tasting Notes:

This is a succinct whiskey thanks to a nose of crème brûlée full of vanilla seeds covered in ripe raspberries, blueberries, and blackberry. That fruitiness edges more towards peaches and pears with a stem and core woodiness next to cinnamon/maple syrup leading towards a touch of menthol tobacco. The end holds onto the cinnamon more than the maple as it slowly fades away, leaving you with a sense of dried apples steeped in cream soda.

Bottom Line:

This is a great example of how unique and kind of funky (in the best way) Four Roses can get. It’s something truly special in the world of bourbon and will be a true palate expander and conversation starter.

Blanton’s Straight From The Barrel

Sazerac Company

ABV: 66.85% (varies)

Average Price: $399

The Whiskey:

Blanton’s is “The Original Single Barrel” bourbon, and this expression is the purest form of that whiskey. The juice in this case is from the barrels that need no cutting with water and are perfect as-is from the barrel. All the barrels will come from Warehouse H (where Elmer T. Lee stored his private stash of barrels back in the day) and arrive with varying proofs.

The through-line is the excellent taste of that single, unadulterated barrel in each sip.

Tasting Notes:

The taste will vary slightly but expect a nose full of very bespoke dark chocolate-covered salted hard caramel toffees encrusted with almonds and pecans — the kind you get from a chocolate shop that imports their goodies from somewhere like Belgium. The nutty toffee carries through into the taste as oily vanilla pods mingle with cedar boxes of dried tobacco leaves and a touch of floral honey. The end is very long and sticks in your senses, with a hot buzzing that subtly fades through all that sweetness.

Bottom Line:

This is one of those bottles that you save for a very special occasion. But it also tastes too good to not crack it open and enjoy. Sure, you could save it and flip it. But, why? Seize the day!

Old Charter Oak French Oak

Sazerac Company

ABV: 46%

Average Price: $469

The Whiskey:

Sticking with Buffalo Trace, this is their 12-year-old bourbon that’s been finished for a spell in French oak. The whiskey is then married and dialed in to really highlight the subtly of that hardwood from France in every sip.

Tasting Notes:

There’s a mix of dried roses, marzipan, and pears on the nose that leads towards a sour cherry counterpoint with a nod towards vanilla-heavy cream soda. The palate holds onto that creamy vanilla while the oak softens towards a wet log floating in a high alpine lake surrounded by fields of wildflowers. A sweet maple sap arrives late as the wood edges towards wet cedar and a hint of cherry tobacco on the short-ish finish.

Bottom Line:

This feels like a very “crafty” bourbon from a huge brand. There’s a unique touch to this whiskey that feels like nothing else coming out of Buffalo Trace. That also means this probably isn’t for everyone. Still, it’s unique, delicious, and very easy to drink.

Weller Full Proof

Sazerac Company

ABV: 57%

Average Price: $472

The Whiskey:

Weller is known for its classic wheated bourbon whiskey. This version is their wheated whiskey that’s presented as-is from the barrel. The Full Proof bourbon goes in the barrel at 114 proof and goes in the bottle at the same proof. There’s no filtering or cutting with water. So you’re getting every nook and cranny from the barrel in the bottle.

Tasting Notes:

This one opens with the essence of cherry that’s been boiled in butter and raw sugar until it’s infused into a caramel candy that’s then wrapped up in vanilla tobacco leaves. A soft pine note comes into play as that caramel and cherry mingle with a hint of vanilla latte dusted with cinnamon. The end is very silky and subtle with a bit of creamy chocolate soda leading back to that vanilla tobacco and cherry caramel.

Bottom Line:

This is one of those bottles that you really wish was much closer to its MSRP of … $50. If that were the case, this would be the perfect everyday sipper with a single rock to really let it bloom. As is, it remains a special bottle at a similarly special price.

Booker’s 30th Anniversary

Beam Suntory

ABV: 62.9%

Average Price: $499

The Whiskey:

Booker’s is Jim Beam’s high-end blend of honey barrels from their vast warehouses. In this case, the limited edition bottle was released to celebrate the 30th anniversary of Booker’s Bourbon. The juice in the bottle is from nine to 16-year-old barrels from very specific parts of the warehouse. The barrels were married and then bottled at cask strength to maintain the beauty of the barrel in the bottle.

Tasting Notes:

Imagine over-ripe bananas simmering in a pan with molasses and butter and a steaming pan of cornbread nearby and you’ll be close to the nose on this one. There’s a hint of wildflowers in honey with cinnamon sticks and whole nutmeg that grows warm on the tongue. Then you’re taken towards a big ol’ bite of a vanilla buttercream frosted pound cake right after a long drag off a cherry-laced cigar. Those notes hold as the fade amps up with the spices, leaving you with a big, long buzz throughout your senses.

Bottom Line:

This might be the absolute mountaintop of Jim Beam. It’s really a spectacular example of the brand with a deeply satisfying vibe from start to finish.

Heaven’s Door The Bootleg Series 2020 Edition

Heavens Door Spirits

ABV: 52.3%

Average Price: $500

The Whiskey:

This is the second installment of Bob Dylan’s Bootleg Series whiskey. This expression is a 15-year-old sourced bourbon that Heaven’s Door finished in Jamaican rum casks. The juice was then bottled at cask strength to hold onto that rumminess.

Tasting Notes:

The nose on this is like unwrapping a dry tobacco leaf from around hot cornbread that’s soaked in melted butter and maple syrup. That buttery corn sweetness persists as fresh slices of juicy apricot arrive next to a touch of dried flowers, eggnog spices, and marzipan. Everything becomes super creamy as the spices, vanilla, and syrup lead towards an almost dry note of cedar and coconut. The end fades very slowly as that coconut browns and dries until you’re left with a fruit, orgeat, and tropical spiced rum vibe.

Bottom Line:

This is a great whiskey to pair in a shredding guitar solo. One where your head slowly starts to bob without you really noticing. Your eyes will shut tightly as the dram slowly heats you to your soul and the guitar shreds you to tears.

It’s not a bourbon. It’s an experience.


As a Drizly affiliate, Uproxx may receive a commission pursuant to certain items on this list.

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