In my last bourbon buying guide, I said choosing an affordable bourbon was hard. Choosing a mid-priced bourbon is even harder. The liquor store shelf is even more crowded; the stakes to your wallet are even higher; so stands the bar. The question looms large: Why blow $35, $40, or $50 on a bottle when you can buy a damn fine one for $25?

Well, that’s the thing. While so much of mid-priced bourbon is marketing chicanery, spending a little more on the right bottle really can open up new boozy opportunities. The best bottles of bourbon for under $50 let you try bourbon pulled from a few special barrels, or just one. The extra money can buy you an older bourbon, or a barrel-proof one. The idea here is to get more flavor, and more experience, by spending a tad more coin. Here are the ones we spring for.

Elijah Craig Small Batch

Distillery: Heaven Hill

Proof: 94

Price: $26-$30

Affordable Gem: A few years ago, Heaven Hill released an Elijah Craig 12 Year that was honey on the lips of many whiskey lovers. When they dropped the age statement and re-released the bottle as “Small Batch,” many were outraged. There was no need. The deliciousness continues, and you can usually get it for less than thirty bucks.

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New Riff Kentucky Straight Bourbon

Distillery: New Riff Distilling

Proof: 100

Price: $40

Hot Young Brand: If you want to try a brand that’s truly new, here it is. New Riff started out in 2014, and touts their sour mash technique and Bottled-in-Bond designation. What that really means is their bourbon is just over four years old, and bold with a high-rye recipe.

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Knob Creek Single Barrel

Distillery: Jim Beam

Proof: 120

Price: $42

A Single Barrel to Love: A high-proof single barrel from Jim Beam—what’s not to like? It ups the spiciness on the already-spicy Knob Creek 9-year, but not too much. Good luck finding someone who doesn’t enjoy this one.

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Old Forester 1920 Prohibition Style

Distillery: Brown-Forman Shively distillery

Proof: 115

Price: $50-$55

Chocolate Bomb: Pretty bottle, tasty bourbon. If you like Old Forester’s 100-proof (an affordable exercise in a classic flavor profile) you’ll enjoy this next step up. Its flavors are even larger and more distinct at 115 proof. The deep dark notes of chocolate and dried fruits, plus a touch of clove and even mint, remind me of Old Forester’s top-end Birthday Bourbon when I first had it.

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Col. E.H. Taylor Jr. Small Batch

Distillery: Buffalo Trace

Proof: 100

Price: $40

Flavor Burst: Buffalo Trace is known for its “classic bourbon flavors” and its rare releases like the Antique Collection and Pappy Van Winkle. Consider the Colonel and his small batch bourbon a shortcut to those flavors, with a lot less strain on the wallet. It’s 100 proof, but tastes like a barrel-proof whiskey. The first time I tried it, I bought a bottle for my dad, who loves smooth sippers. It about blew his damn palate off.

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Four Roses Single Barrel

Distillery: Four Roses

Proof: 100

Price: $45

Unique Single Barrel: Just like Four Roses Yellow, it’s got a high-rye mash bill (60 percent corn, 35 percent rye, 5 percent malted barley). But whereas the Yellow is a blend of barrels using two different mashbills, this one comes from a single barrel. That means a ton more variation than the yellow, plus a sweet, intense flavor.

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Eagle Rare

Distillery: Buffalo Trace

Proof: 90

Price: $30-$40

Buffalo Trace Upgrade: The age statement is an endangered sort of thing these days. Buffalo Trace Distiller’s Eagle Rare stands by it. That’s worth forty bucks, easy, and the fact it’s made using the same recipe as the world-beating George T. Stagg is a cherry on top (more on that here).

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Johnny Drum Private Stock

Distillery: Johnny Drum Distilling Company/Willett (sourced)

Proof: 101

Price: $35-$40

Willett Offshoot: Credit to the “regular guys who happen to like bourbon” over at Breaking Bourbon for this tip: A sub-$50 bottle sourced and released by Willett. Yes, the Willett whose rye and bourbons will make the sub-$100 (and over $100) list of best bourbons. The Willett that the excellent writer Aaron Goldfard declared was “for diehards.” This is a fun little mystery, affordable and tasty.

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Old Ezra 7-Year-Old Barrel Strength

Distillery: Undisclosed

Proof: 117

Price: $40

Sleeping Giant: A barrel-strength bourbon for around forty bucks is a good deal. This one is sourced—Luxco won’t say from where—which is less than ideal. But maybe you can have some fun guessing while enjoying its big old flavors.

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1792 Full Proof

Distillery: Barton 1792

Proof: 125

Price: $45+

Award-Winner: Say hello to the winner of Jim Murray’s World Whiskey of the Year. “Sings on the nose and palate like a wood thrush in a Kentucky forest,” he says. (Murray’s an avid birder, if you can’t tell.) Like all of Murray’s picks, it’s a divisive one. (Even Murray noted that for many years, he rated Barton’s distillery as one of the worst in Kentucky.) It’s well worth a try—if you can find it anywhere.

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Woodford Reserve Double Oaked

Distillery: Woodford Reserve/Brown-Forman

Proof: 90.4

Price: $50

Oaky Beauty: It’s made by re-aging Woodford Reserve Distiller’s Select in virgin charred barrels. The result is a tweak to an already delicious whiskey, adding a layer of oak tannin and vanilla sweetness.

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Wild Turkey Rare Breed

Distillery: Wild Turkey

Proof: varies by year

Price: $45-$55

Big, Spicy Beast: Jim Murray, the divisive reviewer whose Whiskey Bible is known to be writ large, says of Wild Turkey’s rare breed: “it’s still one that would leave a big hole in your whiskey experience if you don’t get around to trying it.” Why? You’re getting Wild Turkey’s bourbon at barrel proof, which is a trick to make any bourbon feel huge. If you’ve had Wild Turkey 101—a high-proof, affordable bourbon worth having—this is the next step up. And it’s a big one. (A comparable Wild Turkey-distilled bottle, Russell’s Reserve, is also worth trying.)

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