If You Like Jack Daniel's, Try These 12 Whiskeys Next

There's an old saying about things being as American as apple pie, but we'd argue that whiskey is up there with quintessential American standouts, too. If you find yourself reaching for the iconic square bottle that is Jack Daniel's, you're definitely not alone. The brand sold 13.4 million cases — not bottles, mind you, we're talking about 9-liter cases — back in 2025, and that's a lot of whiskey. But even if you're a diehard Jack Daniel's fan, it makes sense to want to mix things up a bit every once in a while. The good news is that there are some great options out there if you'd like something that delivers everything you love about Jack while offering something a little bit different. Variety is the spice of life, after all.

We reached out to a few industry experts to see what they recommend to clients, customers, and friends who love Jack but find themselves ready to experiment a bit. They certainly didn't disappoint, giving us recommendations that are bound to please, whether you like the sweetness of Jack or if you're looking for something that's a little more complex.

We spoke with Chris Walster, the whiskey specialist over at The Cask Connoisseur, for some great recommendations, and we also got some advice from Four Seasons Hotel San Francisco bartenders Alvin Liang and Marcus Carnero, Harrah's Resort Southern California mixologist and bartender Teanna Roberts-Abreu, Albert Hotel saloon manager Jessie Zowie, Peck Slip Social co-founder Alex Davis, and Luigi Tartaglia, the head bartender at The American Bar at The Stafford London.

For anyone who's just getting started with whiskey, there are some bad choices to be made, and some very good ones. While overpowering things like peaty Scotch or cask-strength anything might be enough to turn newbies away from whiskey for good, something balanced and easy-drinking — like Four Roses Small Batch — is a great introduction. It's also great for Jack Daniel's fans who are interested in wading into something a little more on the spicy side, while still being easy to drink.

That's a recommendation from Chris Walster. "This introduces more fruit and rye-driven spice while remaining very accessible," he says. "Think caramel and sweet oak alongside red berries and dried spice, with a soft finish." Sounds pretty delightful, doesn't it? You'll also get a little extra kick from that 90 proof sip.

If you're the type who likes to sit and savor, this is the one. There's a long finish that lingers, and from the first whiff, it's easy to see why the brand's Small Batch in particular has been bringing back the awards. As an added bonus, it's excellent in cocktails, too, and is often mentioned as one of the best whiskeys to put in an old fashioned.

Alvin Liang suggests that one of the best whiskeys to try if you're looking for a little bit of a departure from the standard Jack Daniel's is another product out of that iconic Tennessee distillery: Gentleman Jack. It makes sense that this is an excellent way to branch out — as Liang explains, "[It] is produced by Jack Daniel's, so it is still a Tennessee whiskey, but it is a smaller production item. It is aged longer and has a noticeably smoother finish."

The smoothness here famously comes from the combination of limestone spring water and a run through hard sugar maple charcoal. Gentleman Jack gets run through that charcoal mellowing process a second time after it's been aged and before it's bottled. You end up with something smoother, with a little less of the oak-forwardness of the standard Jack.

We happen to think that Jack Daniel's is one of the best whiskeys for a whiskey sour, and we'd also include Gentleman Jack in that category. They both bring something slightly different to the table, and it's a great way to experiment without getting too far out of your comfort zone.

When it comes to awards, few distilleries have earned the accolades that decorate the walls at Uncle Nearest. The name is an homage to the man said to be the father of Tennessee whiskey, and some descendants of Nearest Green are still working at the distillery that bears his name.

That's a lot to live up to, but according to Marcus Carnero, this distillery is putting out a product that would make its namesake proud — and there's a very good reason it's a great choice for Jack Daniel's fans. "Uncle Nearest [is] a Tennessee whiskey whose distiller taught Jack Daniel himself the craft of whiskey making," he says. "It has the slight notes of caramel that can be found in Jack Daniel's, which gives it a nice, smooth finish, [and] it is delicious in a highball."

Chris Walster agrees, telling us that the 93 proof Uncle Nearest 1884 Small Batch in particular is a great one for anyone who wants to stick to Tennessee whiskey, but is ready to try something a little more complex, with layered flavors of brown sugar, caramel, maple, orange peel, and spiciness from pepper and cinnamon. "It keeps the drinker in Tennessee whiskey territory while considerably broadening the flavor profile," he explains. "This is a very drinkable whiskey."

When we ranked Buffalo Trace bourbons from worst to best, the distillery's standard bourbon came in at a completely respectable third place. It's downright delightful, and Chris Walster confirmed to us that when he's making recommendations to Jack Daniel's fans, Buffalo Trace's flagship bourbon is absolutely on the list. "This is where I'd start introducing someone to classic Kentucky bourbon," he explained. "You still get the approachable sweetness, with vanilla, brown sugar, and toffee, but there is more dark fruit, oak, and spice underneath."

You'll also get a slight but manageable boost in proof, too, he notes. Jack Daniel's clocks in at 80 proof while Buffalo Trace sits comfortably at 90 proof — a jump that's noticeable but definitely not offensive.

Teanna Roberts-Abreu agrees that this is a great next step, and told us that it's the sweetness that makes this one a lock: "Buffalo Trace gives you that exact same sweet style with plenty of brown sugar, rich caramel, and vanilla notes. The big upgrade here is that instead of that heavy, smoky, charcoal punch you get with Jack, Buffalo Trace goes down really clean and smooth with a nice hint of oak and spice at the end." As a bonus, it's an outstanding option for anyone who prefers their Jack in cocktail form, as Roberts-Abreu adds that Buffalo Trace is also a great choice for even the fanciest of cocktails.

If you've never picked up a bottle of Old Forester, you're not alone. It's one of the most underrated bourbon brands that you'll wish you knew about sooner, and it's got a pedigree that goes back to the end of the 19th century. There are a lot of choices on the market under the Old Forester name, but Chris Walster suggests that if you're a Jack Daniel's fan, you should reach for the 86 proof.

"Probably my first recommendation," he says. "It stays in approachable American whiskey territory but introduces more fruit, clove, and toasted oak. It is also a part of the Brown-Forman portfolio, so it makes for an interesting sideways step from Jack Daniel's rather than a huge jump into unfamiliar flavors."

This particular expression has brought home a fair share of awards, too, from the San Francisco Spirits Competition and the International Spirits Challenge. That proof means it's just a touch higher than the OG Jack, and when you add in the light spearmint and citrus tones, you get something that's absolutely approachable and sure to please.

Maker's Mark isn't just one of the best bourbons to pair with your steak dinner; it's also one of Chris Walster's recommendations for anyone who wants to reach past the Jack Daniel's bottle and try something a little bit different. It's no secret that some whiskeys can be on the spicy side and feel like an overload on the palate, but Maker's Mark prides itself on being soft, sweet, and smooth. It's well-balanced, comes in at 90 proof, and has a creamy sort of finish that makes it an approachable sip from start to finish.

"[It's] a really good option for someone who particularly enjoys the sweeter side of Jack Daniel's," he confirmed to us. "Maker's Mark uses wheat rather than rye as its secondary grain, giving it a softer style with vanilla, caramel, fruit, and gentle spice."

Luigi Tartaglia also name-dropped Maker's Mark as one of the go-to alternatives for someone who described their usual whiskey as Jack Daniel's. A similarity in profile makes it accessible, but it's different enough to start anyone on their journey to discovering new favorites in a way that's pleasing instead of jarring.

Regular readers will know that we're big fans of Buffalo Trace here, with stellar options like Eagle Rare taking top spots on our list of go-to bourbons. There are a few different versions of Eagle Rare out there, but anyone opting for the 10-year-old — the youngest — will find an incredibly smooth bourbon that somehow manages to pair complexity with that smoothness in a way that's delightful rather than overwhelming. Think toffee and orange, with a little bit of oak and leather, and a little bit of chocolate nuttiness. Sounds amazing, right? 

It is, and it's also a recommendation that comes from Jessie Zowie. "If you're looking for a classic, Eagle Rare 10 Year is a fan favorite for good reason," Zowie told us, adding that the 12-year-old is an excellent next step as well. That one's a slightly higher proof and a little heavier on the oak-and-almond notes, but still wonderfully accessible. Luigi Tartaglia also named Eagle Rare as one of the steadfast recommendations that offers a subtle step up from Jack.

Whiskey doesn't get much more mass-produced than Jack Daniel's, and that's not necessarily a bad thing. You know exactly what you're going to get when you crack open a bottle, and in a world where there are truly few real guarantees, we can get on board with this one. However, Jessie Zowie suggests something a little out of the box for Jack Daniel's fans, and that's Milam & Greene's Single Barrel Straight Bourbon.

Zowie is saloon manager at the Albert Hotel, and the hotel has its own barrel pick of Milam & Greene's bourbon. That's the one that comes recommended, and it's a fascinating leap outside some of the other recommendations we've been talking about. (It's not only available at the hotel, of course.)

The whiskey for this collection is sourced, with each barrel separately evaluated and bottled. As the name suggests, what's in a bottle comes from one barrel (as opposed to being a blend created to capture a certain flavor profile). That means bottles can be very different, and given the number of awards this one can boast, it's a neat way to explore the nuances of a single-barrel whiskey.

Take one glance at a Woodford Reserve bottle, and you'll definitely get some vibes. It looks like this one is going to be a little more upscale, with a sleek bottle, minimal labeling, and a deep color that absolutely shines. Jack Daniel's fans will find that first impression completely accurate, and it's a recommendation — and explanation — that comes to us from Chris Walster.

He told us that this one is a great fit for anyone who likes Jack neat and is interested in finding something that's a little more complex. "There are familiar caramel and vanilla notes, but Woodford adds dried fruit, orange, cocoa, cinnamon, chocolate, and spice. It shows a JD drinker how much complexity American whiskey can offer, without becoming difficult to drink."

Woodford Reserve uses flavor wheels as a graphic representation of what you can expect in each of its expressions, and the flagship bourbon is wonderfully balanced between grains, woody notes, fruits and florals, spice, and sweet aromatics. You'll taste a little of everything without any single one dominating, making it a great natural progression for the whiskey drinker who wants to sit, sip, and take their time with those many aspects.

Jack Daniel's is one of the best whiskeys you can buy for under $30, and so is Wild Turkey 101. According to Chris Walster, the jump from Jack to Wild Turkey 101 is an excellent one to make — especially if you're interested in something with a considerable escalation in that higher-proof, extra-spicy kick that hits you right in the bottom of your throat and goes all the way down.

"This is the next step once someone is comfortable with bourbon and wants something bolder," Walster explained to us. "The familiar vanilla and caramel are still there, but 101 adds more oak, cinnamon, baking spice, and orange peel, with substantially more intensity at 101 proof."

Wild Turkey has been making its 101 proof the same way for decades, and fans will tell you that it's got an unmistakable taste and finish — along with some wildly respectable awards. We also love that this one is great neat, on the rocks, or in a cocktail, as the combination of the higher proof and spicy, rye-based kick means that no matter what you're mixing with it, the bourbon is still going to be front and center. It's one of the best bourbons for even a traditionally sweet cocktail like a mint julep, and since it's on the affordable side of things, it lends itself well to experimentation. What more could you ask for?

We've obviously been talking about one of the most famous Tennessee whiskeys around, so you might be surprised to see an Irish whiskey showing up here. It's not the whiplash you might think it is, particularly because we're talking about Jameson's Black Barrel as opposed to its flagship whiskey. Jameson is a blended whiskey, and in the Black Barrel, you're getting more single pot whiskey that's stronger, nuttier, and spicier — and Chris Walster says it's a great way to move on to another part of the whiskey world altogether.

"My wildcard," he says. "It moves [you] out of American whiskey entirely, but the flavor bridge makes sense. Double-charred barrels give Black Barrel plenty of butterscotch, fudge, creamy toffee, vanilla, and toasted wood, so there is enough familiarity for a [Jack Daniel's] drinker while introducing them to Irish whiskey."

This one, too, makes for excellent cocktails. Jameson itself recommends using this in a whiskey sour, a fancy free (with bitters, maraschino liqueur, cherries, and lemon), or a whiskey buck (with lime juice, ginger syrup, ginger ale, and bitters). If you're entertaining, it's also recommended in various fruity punches — and since so many people love Jack, this recommendation might just save your next holiday party with a little something deliciously different.

Alex Davis came to us with a suggestion for WhistlePig's PiggyBack, a 6-year-old bourbon that checks in at a respectable 100 proof — considerably higher than Jack Daniel's — and has a corn-forward mash bill that means this one is going to be on the sweet side. When this one hit the market, it was with a little bit of side-eye from experts who wondered whether it could live up to the brand's outstanding rye whiskeys. However, some describe it as a perfectly serviceable sort of whiskey, a little on the spicy side, and a good option for standing up in a cocktail.

It's firmly in the category of a bottle you'd keep on your shelf for a regular day rather than a special occasion, which is precisely what Jack Daniel's is as well. Expect caramel, oak, maple, vanilla, and a little bit of tea in there, with an extra kick from the higher proof. We'd suggest this is an option for someone who loves Jack but might want something a touch more on the spicy side. It would also be a great way to dip your toe into something a little higher proof.