Whiskey or whisky — however you spell it, it can make for a great cocktail. We asked bartenders what they thought the most underrated whiskey cocktail is, and the results said a lot: Think more complex flavors and old-school cocktails that have fallen off the radars of many. But there are also nods to classics that you can riff on — while some may say an Old Fashioned is overrated, there are so many takes on it that it could very well be something you’re sleeping on… so ask your bartender for their favorite variation. Here, bartenders share the most underrated whiskey cocktails.

The Most Underrated Whiskey Cocktails:

  • Paper Plane
  • Vieux Carré
  • Whiskey Smash
  • Gold Rush
  • Boulevardier
  • Diamondback
  • Rusty Nail
  • De La Louisiane
  • Manhattan
  • Old Fashioned

Keep reading for details about all of the recommended cocktails!


The Paper Plane is one of the most underrated whiskey cocktails
The Paper Plane

“The underrated whiskey cocktail for me would be a Paper Plane. It’s a fun, bitter sour cocktail with a touch of sweet from the spirits used. It’s an equal-parts cocktail using Aperol, whiskey, Amaro Nonino, and lime. It has layers of flavor and is complex yet approachable. Definitely an underrated whiskey cocktail in my opinion. Try one next time you are out at your favorite bar. Maybe you’ll fall in love with something new.” —Josha Lopez, Beverage Manager, Osaka Miami, Miami

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The Vieux Carré is one of the most underrated whiskey cocktails
The Vieux Carré

“The Vieux Carré is by far the most underrated whiskey cocktail. Paired equal parts whiskey and Cognac, and made more complex with a nice sweet vermouth, [and] Benedictine, Angostura, and Peychaud’s bitters. It’s one of the most complex and beautiful cocktails. It just takes you right back to New Orleans.” —Keith Mrotek, Bar Manager, P.S. Steak, Minneapolis, Minn.

The Whiskey Smash is one of the most underrated whiskey cocktails
The Whiskey Smash

“I’ve always loved a classic Whiskey Smash. It’s a great compromise between an Old Fashioned and a Whiskey Sour. It’s also easy to create any number of variations. Toss in a blackberry, change up the bitters, or split the whiskey with another spirit and you’ve got an entirely different cocktail.” —Shannon Tebay, Head Bartender, Death & Co., NYC

The Gold Rush is one of the most underrated whiskey cocktails
The Gold Rush

“A new aged classic that you don’t see ordered much is the Gold Rush. A simplistic cocktail, yet balanced and soothing.” —Darren Fallon, Lead Mixologist, The Watch: Rooftop Kitchen & Spirits at The Restoration Hotel, Charleston, S.C.

The Boulevardier is one of the most underrated whiskey cocktails
The Boulevardier

“Not so much underrated, but I wish more people would drink the Boulevardier, the perfect balance of bourbon, Campari, and a good quality sweet vermouth with a beautiful orange twist.” —Johnny Swet, Master Mixologist and Founding Partner, JIMMY Rooftop Bar, NYC

“The Vieux Carré is so underrated. Gorgeous whiskey cocktails have roots all over the world, but the Vieux Carré ties so many wonderful spirits from so many places together to make something unique and dynamic.” —Meg Hoberg, Lead Bartender, Sidebar at Bode Nashville, Nashville, Tenn.

The Diamondback is one of the most underrated whiskey cocktails
The Diamondback

“A whiskey cocktail that I think is quite underrated is a personal favorite, a Diamondback: ½ ounce Yellow Chartreuse, ½ ounce Laird’s Bonded Apple Brandy, and 2 ounces of 100-proof bonded rye whiskey (preferably Rittenhouse or Old Overholt). Stir and serve straight up. Delightful.” —Naomi Schimek, Mixologist, Soulmate, Los Angeles

The Rusty Nail is one of the most underrated whiskey cocktails
The Rusty Nail

Rusty Nail. The key ingredient Drambuie [a Scotch whisky liqueur infused with a blend of honey, herbs, and spices] is often relegated to a dusty shelf, but it’s deserving of more frequent use. As opposed to the bland Old Fashioned, the Rusty Nail has tons of complexity packed in the sweetening ingredient, with honey, orange, vanilla, fennel tones, and more. Dust off the Drambuie!” —Rob Krueger, Head Bartender at John Fraser Restaurants, NYC

The De La Louisiane is one of the most underrated whiskey cocktails
The De La Louisiane

“For me, the most underrated whiskey cocktail is a De La Louisiane at a 4:1 ratio. Throw together rye whiskey, Benedictine, sweet vermouth, some absinthe, some Peychaud’s, and my god — you got a beautiful thing. When you’ve been around cocktails a long time, it’s the nature of the game that you’ll have had quite a few. But when your mind whispers out that it longs for a Vieux Carré, or a Sazerac, oooh, or what about a Manhattan riff, too? It could end up with a very fun night. So for me, there are flavor profiles in the De La Louisiane cocktail that tip its cap to so many of those beautiful classic whiskey cocktails. So have one of these, instead of one of everything.” —MacKenzie Conway, Beverage Manager, Fight Club DC popup at Beuchert’s Saloon, Washington, D.C.

“The Vieux Carré. Even though this cocktail is split base, the whiskey is utilized so nicely and blends so perfectly with Cognac and sweet vermouth. The herbaceous aspect of the Benedictine completes this well-rounded yet under-ordered cocktail.” —Jesse Dureka, Head Bartender, Philadelphia Distilling, Philadelphia

“Boulevardier. It’s a classic cocktail that you can drink no matter what the season is. It’s both refreshing in the summer and full of robust flavor for the winter.” —Valeria Murrieta, In-House Mixologist, Estancia La Jolla Hotel, La Jolla, Calif.

The Manhattan is one of the most popular and essential whiskey cocktails.
The Manhattan

“The most underrated whiskey cocktail is a Manhattan. Everyone’s usual ‘go-to’ for a spirit-forward whiskey cocktail is an Old Fashioned, especially since you can make so many variations of it. But many do not realize that you can make just as many (if not more) variations of the Manhattan cocktail as well. Definitely order a Manhattan on your next outing, and ask your bartender to put his/her special touch on it. I guarantee you won’t be disappointed.” —Anthony Baker, Mixologist and Virtual Cocktail “Professor,” NYC

The Old Fashioned is one of the most popular and essential bourbon cocktails.
The Old Fashioned

Old Fashioned. There are 500,000 ways to make an Old Fashioned, and very few people know that there are more variations to this simple drink.” —Jeff Fredeen, Bartender, Crush Lounge, Meritage Resort, Napa Valley, Calif.