I’ve gotten caught up in doing blinds, and I’m realizing that I will need to slow down and focus my efforts on something more significant. So, I’ve decided to do an annual sip challenge. Of course, this won’t be all of the best bourbons on the market, but just what I have in my collection. As I already have some seriously good bourbons on my shelf, this will be an interesting and delicious adventure for me, and hopefully will make some interesting reading for you.
To start with, I’ve had to get a little creative, including with some ground rules. The only bourbons in this challenge are actual bourbons anyone could get at a liquor store. I have several great infinity bottles, including some great “Baby Birthday” bourbons derived from different Old Forester varieties. I could tell you how I made them, but your mix would always be a little different from mine, so those are out. Also out are ryes, including the Jack Daniel’s Single Barrel, Barrel Proof Rye, which is absolutely one of my favorites. That would have easily advanced through the competition, but it’s not a bourbon. I did include some other entries from Jack Daniel’s, even though they’re not “officially” bourbons. I’ll leave the debate between bourbon and Tennessee Whiskey for another day.
I narrowed the field to 64 of my best bourbons, but then I had to break them down into 16-bourbon “regions” to ensure that I was comparing apples-to-apples as much as possible. The regions aren’t perfectly created, but they’re as close as I can get. Each of the regions are seeded, but below are the regions with the competitors in alphabetical order:
High-Proof/ High Value Region:
1792 Full Proof, Baker’s 7-Year Single Barrel, Blanton’s Single Barrel, Bushwood Long Ball, E.H. Taylor Small Batch Bottled in Bond, Four Branches Founders Blend, Green River Full Proof, Henry McKenna Bottled-in-Bond, Jack Daniel’s Single Barrel Barrel Proof, Joseph Magnus Cigar Blend, Kentucky Owl Single Barrel, Old Forester 1924, Old Forester Single Barrel, Penelope Marmallow Toast, Seelbach’s 10-Year Cask Strength, Stagg Jr. #24C
Enthusiast-Level Drams
Bank Street Straight, Benchmark Full Proof, Brother’s Bond Cask Strength, Eagle Rare 10-Year, Evan Williams Single Barrel 2015, Garrison Brothers Single Barrel, High West Rum Cask, Jack Daniel’s Toasted Pecan, John J. Bowman Single Barrel, Old Emmer Cask Strength, Old Forester 1920, Seelbach’s 8-Year Cask Strength, Weller Special Reserve, Wild Turkey 101 8-year, Wild Turkey Rare Breed, Yellowstone Single Barrel
Solid Everyday Sippers
1792 Single Barrel, Benchmark Single Barrel, Buffalo Trace, Bulleit Bottled in Bond, Chattanooga Bottled in Bond, Daviess County Toasted, Early Times Bottled in Bond, Elijah Craig Small Batch, Four Roses Single Barrel OESO, George Dickel Bottled in Bond, Heaven Hill Bottled in Bond, High West Chardonnay Cask, Jim Beam Single Barrel, Old Forester 1897, Old Grand-Dad 114, Nelson Brothers Reserve
Entry-Level/ Value Buys
Angels Envy Port Finished, Bowman Brothers Small Batch, Burlock & Barrell Reserve, Clyde May’s 6-Year, Evan Williams 1793, Evan Williams Bottled-in-Bond, Jack Daniel’s Bonded, Jack Daniel’s Single Barrel, Knob Creek 9-Year, Maker’s Mark, Member’s Mark Small Batch, Old Forester 100, Old Forester 1910, Russell’s Reserve 10-Year, St. Augustine Straight, Wild Turkey 101
(If you want to see the entire bracket, you can access the initial PDF here: Ultimate Sip 2025 Initial.)
Each write-up will involve two blinds of four bourbons (two different matchups of two placed together into a blind that helps obscure the various bourbons I’m sipping). The winners will be advanced into the next round. I’ll be doing three write-ups each week, and the entire competition will take just over one month. We will start with the first write-up here, and the next one will follow on Tuesday.
First Round – High-Proof/ High-Value Region (Top Half)
The first blind: Old Forester Single Barrel vs. Bushwood Longball; Kentucky Owl Single Barrel vs. Penelope Marshmallow Toast
Glencairn #1: Really nice, rich color, but the nose is unimpressive. It’s a little sweet, but I had a hard time identifying anything other than sweet sugar. The flavor was a little off-putting, almost like sweet tobacco at the front. There were other flavors there – a little vanilla and caramel, but it was just earthy in a way that wasn’t completely enjoyable. There was a nice, soft mouthfeel, but that helped keep this on the tongue longer than I liked and led to a less than great finish. Honestly, it wasn’t terrible, but it wasn’t wonderful either. Score: 69.
Glencairn #2: Even though I mix up the Glencairns to obscure which bourbon I’m tasting, I’m immediately almost certain that this is the Old Forester Single Barrel. The color is rich and beautiful, and the aroma does not disappoint the nose. Classic wafts of cinnamon, caramel and toffee drift in, along with a hint of banana. All of those things are also present on the palate, and there’s such a creaminess on the mouthfeel that those flavors hang out for a long time. There’s some warmth here, presumably from some decent proofing. Score: 80.
Glencairn #3: I also suspect this one’s identify, and it’s the Bushwood Longball. We’ll see. There’s some nice color to it, but the aroma is almost as weak as the first sample. Frankly, it’s just above undetectable. I’m picking up a little oak and vanilla, but nothing to make me excited to drink what’s in the glass. The flavors are nice, but fairly basic. Vanilla, caramel, oak, maybe a little baking spice, but not much complexity, and a fairly thin mouthfeel. The finish lingers just long enough to enjoy the sip for a bit and then disappears. Score: 60.
Glencairn #4: The color here is about the same as with #3 – a pleasing amber – but the aroma jumps out with more brown sugar and rich caramel. The flavor does not disappoint with notes of apple, cinnamon and those same sugar and caramel notes from the nose. There’s definitely some heat, maybe from proof or rye, but that doesn’t overwhelm what I’m tasting. The mouthfeel is a little syrupy, and that helps the finish develop with some additional fruit notes, though I couldn’t pinpoint what I was tasting there. Overall, this is easily the second-best one in the group. Score: 72.
The unveiling:
Glencairn #1: Penelope Marshmallow Toast
Glencairn #2: Old Forester Single Barrel
Glencairn #3: Bushwood Longball
Glencairn #4: Kentucky Owl Single Barrel
The results:
Old Forester Single Barrel 80, Bushwood Longball 60
Kentucky Owl Single Barrel 72, Penelope Marshmallow Toast 69
Old Forester Single Barrel and Kentucky Owl Single Barrel advance to the Round of 32.
The second blind: Seelbach 10-Year vs. Baker’s 7-Year Single Barrel; Stagg Jr. #24C vs. Green River Full Proof
Glencairn #1: Fair color, kind of a light amber, but the aroma surprises with some solid vanilla, caramel and baking spice. These continue on to the palate, where the flavors exist in a pleasing balance, along with some nice spice. This is a nicely creamy sip, and the experience continues to the finish, but there it starts to drift a little too early. It’s not bad, but it’s less than I expected, with the flavors losing out to a little too much ethanol on the back end. Score: 70.
Glencairn #2: This almost looks like a glass of port wine, and the aroma carries some of those port notes as well, smelling a bit of raisins and berries, mixed with the traditional aromas of bourbon. On the palate, the richness comes immediately through with creamy red fruit balanced with baking spice and just enough vanilla. That creamy, syrupy mouthfeel pins the flavors to the senses, and they remain and develop through a lengthy and enjoyable finish. Score: 77.
Glencairn #3: I really like this dram, starting with its rich, copper color and moving into its aroma, which is full of nuttiness and hints of cherries and apples. On the tongue, this makes my taste buds dance with notes of chocolate, caramel, spice and a bit of oak. I’m not sure if I enjoy this more than #2, but it’s close. There is a lovely feel of syrup, and the finish is one of the best so far, with the flavors not wanting to leave. I think #2 gets the edge because of a slightly better complexity, but this one’s a contender. Score: 74.
Glencairn #4: Oh crap. This one’s a contender, too, and that means that I’m losing a really good bourbon right off the bat. The color here is equal to #3, and so does the aroma, which is full of butter, chocolate and caramel, with a nice bit of baking spice (nutmeg?) in there. The flavor jumps out with chocolate-covered caramels, but the hero is the cinnamon, which floods the mouth and stays through into a beautiful finish. As much as I like #3, I have to admit that #4 is ever-so-slightly better, though it probably lags behind #2. Score: 75.
The unveiling:
Glencairn #1: Baker’s 7-Year Single Barrel
Glencairn #2: Seelbach’s 10-Year
Glencairn #3: Stagg Jr. #24C
Glencairn #4: Green River Full Proof
The results:
Seelbach’s 10-Year 77, Baker’s 7-Year Single Barrel 70
Green River Full Proof 75, Stagg Jr. 74
Seelbach’s 10-Year and Green River Full Proof advance to the Round of 32.
Next post: The bottom half of the High-Proof/ High Value Region on Tuesday, June 10.
Copyright © 2025 Doug DeBolt
