6 Bottles Of Jack Daniel's Whiskey, Ranked Worst To Best

Ah, Jack Daniel's. It's a classic whiskey instantly recognizable by the signature black and white label, at least the one found on the brand's famous Old No. 7. I mean, it is definitely the most iconic. What about the rest of the spirit company's lineup, though? Does the standard Jack Daniel's Old No. 7's legendary status carry the brand, or do the other whiskies pumped out of the distillery deserve a second look? My guess is it is a little bit of both. After all, Jack Daniel's is a must-know brand for beginners. Still, assumptions will get us nowhere. That's why I went on a mission to find out.

I tasted and evaluated six different bottles of Jack Daniel's Whiskey, so we never have to wonder how they stack up again. I also ranked them from worst to best based on taste, perceived quality, price, proof/ABV, versatility, and mass appeal. More on my methodology can be found at the end, but all in good time, my friend. Before we get into that, let's find out how several of the brand's offerings stood up in a head-to-head competition. Will the classic Old No. 7 still reign supreme? Or, is it just a starting point for anyone who loves the brand? Let's find out!

Some recommendations are based on first-hand impressions of promotional materials and products provided by the manufacturer/distributor/etc.

Here's the thing: Jack Daniel's Tennessee Blackberry isn't bad, per se; it definitely isn't my cup of tea, though. As a result, it lands in last place in my ranking. You can snag a 750 ml bottle for around $18.99, so it's priced just right. However, it's way too sweet for my liking. Additionally, as a flavored whiskey, the proof (70) is slightly lower than that of all but one of the Jack Daniel's bottles I compared.

As for flavor, Jack Daniel's Tennessee Blackberry did, in fact, taste like blackberries, and there was a nice whiskey flavor to back it up. These qualities made it incredibly easy to drink straight. I could see how it might be good for a whiskey beginner or someone looking to pound shots. Still, if you are looking for a taste of the good stuff, pure and simple, it isn't for you. The overwhelming blackberry flavor also makes it significantly less versatile than a straight-up whiskey recipe. With this in mind, I'll be passing on it from now on.

Admittedly, Jack Daniel's Tennessee Blackberry is much tastier than Crown Royal Blackberry — I tried it recently and wasn't impressed — but that still didn't earn it a spot higher than last place. That's okay, though. There isn't really anything wrong with it; the upcoming bottles simply have it beat regarding flavor, quality, versatility, and mass appeal.

Next up is none other than Jack Daniel's Old No. 7. As the brand's classic original, almost anyone can recognize it, whiskey connoisseur or not — so you may be surprised to find it in my second-to-last position. Consider this more of a nod to the upcoming bottles than a slight to Old No. 7, though. I know it is an iconic bottle, especially for anyone looking for an affordable pick (a 750 ml bottle costs about $17.99, after all). Heck, even Martha Stewart uses it in her whiskey sours. It just didn't outperform the four higher-ranking bottles.

The moment I got a whiff of my Jack Daniel's Old No. 7 pour, I was transported back to my party days. However, after I got a taste, I quickly remembered why I upgraded to more premium picks long ago. Compared to most of the other bottles I sampled, it was a bit rough around the edges and extremely sweet for an unflavored whiskey. It's alright for pairing with heavy mixers, like Coke or juice, but that's where the fun stops for me.

Long story short: If you are looking for a no-frills budget bottle of whiskey, you could do a whole lot worse than Old No. 7. It's 80 proof, priced super low, and there's no denying its legendary status. Even so, I'd much rather spend $6 more and go for my number two pick. Old No. 7's too sweet for me, and honestly, it screams low quality.

Coming in fourth place is Jack Daniel's Single Barrel Select Whiskey, and let me tell you: It's miles ahead of the two bottles that are ranked lower. Actually, it blows them out of the water regarding mass appeal, quality, versatility, proof, and flavor. The only area where it falls behind is price. A 750 ml costs about $46.99, so it's the most expensive bottle on our list. Even so, if you are looking for a premium pick, it more than fits the bill.

Everything from the label to the shape of the bottle alerts you to the fact that Jack's Single Barrel Select is a premium product. Fortunately, the taste backs it up, too. After a couple of sips, I relished the way the subtle sweetness and notes of caramel progressed across my palate. There was no lack of complexity, either. It also boasts a 47% ABV, making it the second-highest proof I sampled. Translation: The higher ABV not only gets you more alcohol, but it also leads to a more robust whiskey flavor. Winning! With this in mind, I wouldn't dream of weighing it down with a heavy mixer (one of several whiskey cocktail mistakes), best to drink it straight.

Would I pay double what Gentleman Jack costs for Single Barrel Select? Maybe for a special occasion or to give to a connoisseur, but it certainly wouldn't be an everyday pick for me. That's where my top three come into play.

The award for third place goes to Jack Daniel's Tennessee Fire. It may have a lower proof (70) than some of the others, but oh man, did it hit the spot. Plus, for the fantastic price of $18.99, you can get a 750 ml bottle, and that's something anyone can get behind.

First things first: Before this, when I thought of cinnamon-flavored whiskey, Fireball was the only thing that came to mind. Not anymore, though. Instead of tasting like regret (yes, that's what Fireball tastes like to me), Tennessee Fire made me want to turn up the tunes and laugh with friends. Seriously, it's infinitely better than that which shall no longer be named. It boasts lots of delicious cinnamon flavor, and the whiskey notes are the icing on the cake. My pour went down smooth and easy without a second thought. Actually, now that I think of it, that makes Tennessee Fire quite dangerous, but who cares? Unlike blackberry, whiskey and cinnamon are a perfect pairing. Additionally, even the newest whiskey drinker could easily savor it straight.

Tennessee Fire may not be the most versatile bottle, and it's unlikely to be a go-to pick for someone looking for a classic pour of our favorite brown liquor, but that's okay. College kids and anyone else looking to get the party started better watch out, though, because if you aren't careful, the entire bottle will be gone before you know it. Ask me how I know.

Holding down the number two spot on my list is Jack Daniel's Gentleman Jack. It only costs about $6 more than Old No. 7 — $23.99 for a 750 ml bottle — and it has the same 40% ABV, but it's miles ahead in the quality and flavor department. In fact, Old No. 7 is one of several bottles connoisseurs say are best left on the shelf, but not Gentleman Jack. It's pretty darn tasty.

Jack Daniel's Gentleman Jack isn't nearly as sweet as Old No. 7 (one of the biggest complaints about the bottle), and it has a much smoother finish. The label also describes it as "double mellowed." I'm not exactly sure what that means, but compared to its more affordable cohort, it does, in fact, taste more mellow with rounded edges. I also detected way less burn. As a result, Gentleman Jack is a bottle you could feel good about drinking straight, in a Manhattan, an Old-Fashioned, or any other cocktail that doesn't rely on heavy mixers to mask sub-par whiskey. Suffice it to say, it's very versatile thanks to its premium flavor profile. You'd never guess it was so affordable by taste alone, either. Nicely done, Jack Daniel's!

The only reason Jack Daniel's Gentleman Jack didn't lock down the first-place spot in my ranking is that the bottle that did blew me away. It's more complex, refined, and well, it just tasted better. So, without further ado...

Hands-down, Jack Daniel's Bonded Rye was the best bottle of the bunch. In fact, if you don't fancy yourself a rye drinker yet, I'd even go so far as to say it has what it takes to make you join the fan club. For starters, it is 100 proof, so you get plenty of bang for your buck in the flavor and price department. Speaking of which, it also comes with a reasonable price tag of about $30.99 for a 700 ml bottle. If you're keeping track, that's a touch smaller than the other bottles, but that'll be the least of your concerns once you get a taste.

Jack Daniel's Bonded Rye was smooth and spicy, as any good rye should be. Best of all, the flavors danced across my tongue beautifully. It is nothing if not complex. One sip and I was like, "This ain't your average whiskey — it's a rye! And I, for one, am here for it!" It was simultaneously sweet and bold without being overly saccharine. Obviously, it's 50% ABV means it packs a punch as well, but it's one I'll happily take. The higher proof also results in better spice and complexity in a nuanced way. Yum! I could easily see myself enjoying a glass of Jack Daniel's Bonded Rye neat, but its bold flavors also make it ideal for an Old-Fashioned and other classic rye cocktails. So, in the end, it had to come out on top.

Whiskey as a whole is far from a one-trick pony, and the same can be said about the Jack Daniel's brand. It produces whiskeys in various flavors, styles, proofs, and more, so it can be challenging to pick the right bottle. To help make things simpler, I personally tasted and evaluated the six bottles found above. As a bartender and server for 20 years, I already had more than my fair share of experience with Jack Daniel's to go on, but don't worry, I didn't mind.

After several sips of each Jack Daniel's bottle found above, I ranked them based on taste, perceived quality, price, proof, versatility, and mass appeal. And yes, I drank them all straight, no ice or chilling (two things that easily dilute flavor). In the end, the bottles that boasted better quality and more nuanced flavor profiles rose to the top. Even so, none of the products were downright awful; they just weren't all for me. Still, if you want to step up your whiskey game and leave the amateur picks behind, I recommend you opt for one of my top four. They cover all the bases — premium, flavored, rye, and great quality — and they definitely taste significantly better than the bottom two. Now, all that's left to do is find out whether Jack Daniel's is considered whiskey or bourbon, and you'll have the brand covered. Cheers!