The Bourbon Cheapskate, Vol. 22: The Best of $40 and Under (New Year’s Edition)

Every year, I buy more bourbon than I need and discover more bottles than I expect. Some disappoint. Some surprise. A few elbow their way into permanent shelf space.

This list is the last category.

These are my Top 10 Bourbons Under $40, counting down—not because they’re cheap, but because they punch far above their price and belong in any serious rotation.

No gimmicks. No hype. Just bottles that showed up again and again in blinds and earned their spot.

🥃 The Top 10 (Countdown)

10. Bank Street Straight

The first real surprise of the year. A Total Wine Spirits Direct bottle that kept showing up strong in blinds. It doesn’t scream for attention—it just quietly outperforms expectations. That’s exactly how bargains should behave.

9. Old Forester 100

This one shocked me—not because it made the list, but because it didn’t climb higher. Still, when everything here is a winner, landing at #9 says more about the field than the bottle. Rock-solid, reliable, and endlessly useful.

8. Sleight of Hand

Most people haven’t heard of this one, and that’s a shame. This Ironroot Harbinger whiskey is distinctive, well-crafted, and absolutely worth shelf space. It rewards attention and stands out in a sea of sameness.

7. Sazerac Rye

The only rye on the list—and it could easily be the only rye you own. It hits well above its weight, works beautifully neat, and absolutely sings in an Old Fashioned. A true utility player that never feels boring.

6. Maker’s Mark 46

Yes, it has a screw top. No, I don’t care. This bottle is creamy, rich, and downright delicious. It’s one of the best expressions Maker’s offers, and it earns its place every single time.

5. Old Grand-Dad 7-Year Bottled-in-Bond

This is where the list starts reaching toward the top shelf. A clear upgrade from the standard BiB, with more depth and maturity while keeping that classic Old Grand-Dad backbone intact. Serious bourbon at a still-friendly price.

4. Wolcott Rickhouse Reserve

Another surprise—and one I resisted for far too long because it came with a Total Wine suggestion sticker. Lesson learned. This bottle wins me over every single time I taste it. Weird origin story or not, it flat-out delivers.

3. Rebel Single Barrel – Kyle Busch

A late-year addition and an immediate favorite. Cherries jubilee set on fire. Bold, rich, and unforgettable. I bought this within the last month and instantly knew it belonged near the top. Absolute must-have.

2. Cooper’s Craft 100

If this were sold everywhere, it would be talked about constantly. A Brown-Forman gem that feels decadent without punishing your wallet. You must have this on your shelf if you can find it.

🥇 1. Old Grand-Dad 114

The dean of the Bourbon Cheapskate shelf.

You’ll never pay more than $35 for it—usually closer to $32—and it delivers velvety texture, rich flavor, and unapologetic proof. This bottle has been doing the work for decades, and it still embarrasses bottles twice the price.

Go get one. Today.

❌ Just Missed (Price Got in the Way)

These all hover in the $45 range, which knocked them out of the Cheapskate countdown—but don’t mistake that for a lack of quality.

3. Russell’s Reserve 10-Year

We already know this one’s great. An all-around almost-bargain hero that just barely misses the cut.

2. Heaven Hill Bottled-in-Bond

Winner of my bottled-in-bond challenge earlier this year—and that’s saying something. One of the most satisfying classic pours out there.

1. Copper & Cask Private Batch

Found at BJ’s Wholesale Club, and while it’s not mind-blowing, it’s awfully close. If this had slipped under $40, it would have walked away with the top spot.

🏆 Cheapskate Bonus Awards

These bottles weren’t part of the countdown—but they deserve recognition.

Best Under $30

Benchmark Full Proof
Holy smokes. Usually $25–26, but I just saw it for $23 at Shores Liquor. It holds its own against high-proof bourbons that cost twice as much.

Best Under $25

Benchmark Bonded
Take everything I said about the Full Proof and dial it back just a touch. Still excellent, still rich, and still a ridiculous value.

Best Under $20

Member’s Mark Bonded
A Sam’s Club special that absolutely hits home runs. At $19, this bottle has no business being this good. Rich, flavorful, and easily worth $10 more than the price tag.

Final Thought

None of these bottles made the list because they were cheap.
They made it because they earned it.

If you’re building a bourbon shelf on a budget—or just don’t like overpaying for hype—this list will serve you well all year long.

Here’s to great bourbon, smart buying, and another year of excellent pours. 🥃