The Best Bourbon Cocktails Every Home Bartender Should Know

Created by bartender Erick Castro at Rickhouse in San Francisco, the Kentucky Buck is a bourbon, ginger and strawberry cocktail that’s great with a ginger beer, but even better with fresh ginger syrup and sparkling water. If it sounds like a Moscow Mule with bourbon and strawberries it’s because that’s exactly what it is, but the mule was passé by that point in San Francisco, so Castro reached deeper into history for the name. A “Buck” is a style of cocktail that dates back to the 1890s—long before the Mule or the Dark ‘n Stormy—and was composed of just a spirit (usually whiskey) and ginger beer, so named because the ginger and alcohol together would give quite a kick (the Moscow Mule is named similarly, for the kick).

Muddle the strawberry in the bottom of a cocktail shaker. Add bourbon, lemon, ginger syrup, and bitters, and shake for six to eight seconds. Strain over fresh ice in a tall glass and top with soda water. Garnish with a half strawberry or a lemon wheel or a mint sprig or all three.

The Gold Rush—whiskey, lemon juice, and honey syrup—is a good and important drink, but we admit we don’t love it:  “The Gold Rush as it’s normally constructed,” we write, “will be forever stuck in third gear until you do something to push it to the next level.” Fortunately, that something can be as easy as spicing it with ginger, perfuming it with florals or smoke, or easier still and our favorite version, adding a grapefruit peel to the shaker tin before shaking on ice. This so called “regal shake” transforms the cocktail, adding complexity and depth.

Add all ingredients, including grapefruit peel, to a cocktail shaker with ice. Shake hard over ice for 8 to 10 seconds, and strain into rocks glass over fresh ice.

This is a drink that practically started a cocktail revolution on its own. When bartender Don Lee decided he wanted to add bacon to a drink while working at famed bar PDT in New York, he eventually came upon the technique called fat washing, that chefs at experimental restaurant WD~50 had been toying with. To get the flavor of bacon without the greasiness, Lee and Co. found that he could combine bourbon and bacon fat, then freeze the mixture and strain out the solids, leaving a spirit infused with the flavor compounds behind. Now numerous cocktails are made with fat-washed spirits that add an exciting layer of flavor (like our Olive Oil Martini), but the Benton’s Old Fashioned is the originator and one of the best.

Benton’s Old Fashioned

Add a large piece of ice to a rocks glass, add liquids, and stir for about 10 seconds. Express the oils of an orange peel over the top and place the peel in the drink as a garnish.

*Bacon-infused Bourbon

Put two or three strips of bacon in a pan, and heat gently and slowly—you want to make extra sure not to scorch or smoke the fat. When the bacon is almost cooked, pour off the liquid rendered fat into a separate container. 

You need 0.5 oz. (1 tbsp) of fat for every 8 oz. of bourbon, so start with that ratio and scale up if you desire. Combine the two in a non-reactive container and stir. Let sit at room temp for four to 24 hours, then transfer to the freezer until frozen (about 2hrs). Strain the liquid off the now-solid fat through a coffee filter or cheesecloth, and it should be totally clear. 

Of the 10 million or so variations on the Negroni the Boulevardier is probably the oldest and almost certainly the best. A mixture of bourbon, Campari, and sweet vermouth, the Boulevardier replaces the prickly gin with the broad oaky shoulders of a good American whiskey, bringing a welcome touch of vanilla to Campari’s orange. It’s branchy herbaceousness, ample fruit, and bittersweet character fit into the season perfectly, equally at home in both warm and cold weather, and either before or after dinner,

Add ingredients to a rocks glass with ice. Stir for 10 seconds if the ice is small, 30 seconds if one big cube and somewhere between if ice is somewhere between. Garnish with an orange peel.

Picture yourself in the yard grilling meat, the direct sun still uncomfortable in the late afternoon, on one of those days when you wonder if it’s an acceptable hour to start drinking and then decide you don’t care either way. And if you’re anything like me, you are often met with a set of conflicting instincts: It’s too hot for whiskey, but you kinda want whiskey. The temperature forbids sweetness, but you want it refreshing and summery. You don’t want a glass of juice, but you’d love the overall effect to be juicy. It’s like a riddle. What to do? You drink a Cardboard Plane. It’s the child of Sam Ross’s incredible Paper Plane, yet it’s fresher than its predecessor, with more citrus where the other would have herbal complexity, but with a similar textured bitterness and tart finish.

Add all ingredients to a cocktail tin and shake hard on ice. Strain into a rocks glass over fresh ice and garnish with a grapefruit peel.

If you only ever drink one cocktail that may or may not have been created inside a building shaped like a bowler hat, let it be a Brown Derby. Of course, the origins of the drink weren’t in Hollywood after all, but let’s not allow that to distract us. The drink we’ve come to know as the Brown Derby is a combination of whiskey, grapefruit, and honey. However, the addition of a little bit of lemon juice gets the balance of this lesser-known drink right and turns it from pedestrian to outstanding.

Add all ingredients, including grapefruit peel, to a cocktail shaker with ice and shake good and hard for eight to 10 seconds. Strain off the ice into a rocks glass over fresh ice or up in a coupe (your choice), and garnish with

This Old Fashioned variation is an Improved Whiskey Cocktail (whiskey, maraschino, bitters, and absinthe) without the absinthe. True, getting rid of just a spoonful of absinthe isn’t a huge reinvention, but that lack of the spirit’s strong flavors lets the marschino really shine in the Fancy Free.

Fancy Free

Build in an Old Fashioned glass over the biggest piece of ice you have. Stir 10 to 15 seconds and garnish with an orange peel.

Every Derby Day festoon their heads with elaborate hats, fill metal cups with a minty bourbon cocktail, and prepare to watch the horsies run. We’re not here to quibble with a single one of those traditions—especially since more people tuned into the 2024 Kentucky Derby than in 35 years, so Americans are still clearly enjoying the spectacle. However, that doesn’t mean we can suggest a little twist on what you’ll be drinking the next time the Derby rolls around. The Georgia Julep intermingles the fresh mint with the juicy sweetness of peach liqueur.

Georgia Julep

In a metal cup, gently muddle the mint into the peach liqueur. Add the Cognac or bourbon, and fill 2/3 with crushed ice. Stir to chill, until a frost forms on the outside. Then pack the rest of the cup with ice. Take two mint crowns, lightly bruise them with your fingers, and stick them against the inside close to the straw. Enjoy.

This classic from 1937 is the perfect autumnal whiskey drink, with half its soul in summer and the other half in winter. On one hand, it’s made refreshing with lime juice, and is totally suited for backyard barbecue sipping. On the other, the recipe incorporates a small but significant amount of allspice liqueur, which gives it an avalanche of textured spice that finds it a home by the fire. The Lion’s Tail is a transitional drink that tastes like if a Jamaican jerk chicken and a Whiskey Sour couldn’t keep their hands off each other.

Add all ingredients to a cocktail shaker. Add ice and shake hard for eight to 10 seconds. Strain off the ice into a cocktail or coupe glass. Garnish with a lime peel, a lime wheel, or nothing at all. 

Born in the California beach enclave of Montecito, the Napoleon comes by its refreshing summer vibes honestly, even if it is made with a seemingly unsummery spirit. Sam Penton at the Manor Bar at the Rosewood Miramar took a high-proof bourbon and the basic structure of a whiskey sour and added some fruitiness and herbaceousness to make this a well-rounded cocktail. The addition of strawberries, vermouth, and Campari are welcome modifiers to the old classic, and their sharpest edges are sanded off with the presence of an egg white to keep it as mellow as you want a summer drink to be.

Add all ingredients to a cocktail shaker without ice. Seal the shaker, hold tight, and give it a “dry” shake without ice for three to five seconds. Then add ice, seal again, and shake for eight to 10 seconds. Fine strain into a coupe or cocktail glass.

The problem with adding smoke to your cocktails is that it’s a blunt tool that’s so easy to use wrong. When you’re out at a bar and see the glass cloche filled with smoke lifted to reveal a drink inside, it’s a pretty safe bet that the cocktail will not be good. Smoking a cocktail like that is far too imprecise. But there is a better way to smoke your cocktail and in an episode of our Cocktails for Grown Ups, we show you how to do it. First, we demonstrate how you can smoke your syrup if you’re making a bunch of smoky drinks. Second, we show you our method when you’re making just one drink at a time. The smoky cocktail in question here is the Palo Santo, one created for the Michelin three-star restaurant Addison.

Palo Santo

Combine ingredients in a mixing glass with ice and stir for 10 to 25 seconds (shorter for small ice, longer for big ice). Then, put a piece of palo santo wood on a non-reactive surface (stainless steel, a cast iron pan, or just a larger piece of different wood) and burn it with a blowtorch until it starts to smoke. Invert your glass over the smoke and let it infuse there for eight to 10 seconds, then flip the glass right-side-up, allowing the smoke to escape. Then add ice to a rocks glass and strain the drink over that fresh ice, and garnish with an orange peel.

We write that the Paper Plane is “like a whiskey and orange juice that grew up handsome, and for whom everything is going right.” This crowd pleaser, invented by bartender Sam Ross in 2008, gets its charm from two different bittersweet Italian liqueurs, even though the resulting cocktail is neither particularly bitter nor sweet. It is simple to make, and easy to like and “might be,” we claim, “the best cocktail invented in the last 100 years.”

Add all ingredients to a cocktail shaker with ice and shake for six to 10 seconds. Strain up into a coupe or cocktail glass.

It’s the granddaddy of them all. The Old Fashioned first appeared in print in 1880, but surely existed before then. The name is fitting, as it’s a timeless classic. It’s simple and malleable, thus tweaked constantly by bartenders for well over a century. But sometimes its just great to come back to the original.

Assemble ingredients in a rocks glass, add ice (the bigger the better) and stir for 8 to 20 seconds. Smaller ice will need less stirring. Remove a thin piece of peel from a lemon (for rye) or orange (for bourbon), getting as little of the bitter white pith as possible; hold the peel between your fingers with the outside facing the top of the drink and pinch slightly to express the citrus oils over the top.

A Stinger is a classic cocktail, a two-step of Cognac and creme de menthe. The Midnight riff comes to us from Sam Ross, then of the legendary Milk & Honey, and turns the classic into a sour, bringing lemon juice to tart up the old Stinger profile but subbing bourbon for Cognac and Fernet Branca for the mint liqueur. And while it seems rude for mint to RSVP only for Fernet Branca to show up, it turns out that arriving with bourbon is a good way to be let in the door. The cocktail is a fantastic way to get acquainted with Fernet Branca, and who knows? Give it some time and you might even come to like it.

Midnight Stinger

Shake four to six seconds on a handful of crushed ice, pour ice and cocktail into a rocks glass, pack with more crushed ice, and garnish with a mint sprig.

“I created this drink,” wrote legendary bartender Dale DeGroff in his 2008 book The Essential Cocktail, “because, frankly, I was a little bored by Mint Juleps, which have a tendency to be too sweet and too uncomplicated.” So he began making a drink at the Rainbow Room he called the Whiskey Smash—the familiar whiskey, sugar and mint, but this time, with lemon wedges added to the mix, muddled with the mint into a pint glass and the whole thing shaken together. Whether or not he was right about Juleps, he’s dead-on that the addition of lemon completely changes the nature of the cocktail, a leap to an entirely distinct cocktail family tree. Now, we’re in Whiskey Sour territory, and the mint and lemon proved to be outstanding solutions to the Sour’s original problem. The addition of mint—plus, importantly, the extra lemon oils extracted from muddling the wedges as opposed to just using juice—transforms the bourbon not just into a summer drink, but an especially fresh and radiant one, with the zestiness of the lemon oil and the mentholated fireworks of the mint providing some deliciously deft misdirection from the tannic sore thumb that tends to weigh down whiskey sours.

Add all ingredients, including mint and lemon peel, to a shaker tin. Add ice, shake hard for six to 10 seconds. Strain over fresh ice into a rocks glass, garnish with a mint crown and enjoy.

“Is there a more agreeable drink than a well-made Whiskey Sour?” we asked last summer, and we’re still not sure there is. Whiskey, with its broad shoulders and oaky fullness, can be almost completely disarmed by tarting it up with fresh lemon juice and balancing with simple syrup, as bartenders have been doing since roughly forever. We say “almost” because often (though not always) you need a little extra push by way of an egg white.

Add all ingredients to a shaker tin. “Dry” shake ingredients without ice for five seconds to whip the egg. Add ice, seal tins, and shake hard for 10 to 12 seconds. Strain into coupe, Martini glass, or rocks glass—it’ll come out white at first, and the color will emerge over the course of a minute under a paper-smooth head of foam. Express a lemon peel over the top of the foam for aroma and discard and decorate the foam with a few drops or dashes of Angostura Bitters.

In 2004 in San Francisco, everyone who was doing “mixology” was leaning into the region’s year-round availability of fresh produce, so the city’s cocktails were full of things like satsuma mandarins and fennel bulbs and garnished with fistfuls of lemon balm. Jon Santer, with his Revolver, went a different way. This dark and broody Old Fashioned variation is, we claim, “among the best cocktails in the neo-classic pantheon,” and comes with a bonus kick of caffeine to help with the shift back to standard time, for when you go to Happy Hour and it’s already pitch black outside.

Add all ingredients to a rocks glass over a large piece of ice and stir. Garnish with a flamed orange peel or a regular orange peel.

The Ponton Smash is a whiskey drink cosplaying as a rum drink. It’s whiskey slipping a lei around its neck and pretending it was always designed for the summertime, and what’s more, it’s actually pulling it off. It’s refreshing and tropical, herbaceous and bright, and the reason it works—the reason this is one of the only tiki bourbon drinks you’ll ever see—isn’t because of an unusual build or beachy origin or some exotic tree-sap unearthed from the Bornean jungle. It’s simply due to the transformative magic of a well-chosen absinthe. So for this we us Butterfly Classic Absinthe, it’s character perfectly complementing this drinks other ingredients.

Add all ingredients to a cocktail shaker and shake hard on ice for six to eight seconds. No need to muddle the mint, the ice with “smash” it for you. Fine strain into a rocks glass over fresh ice, and garnish with a mint sprig, and if you’re feeling festive, a pineapple slice or leaf.

We hear you thinking. “The Amaretto Sour? I thought this was about whiskey drinks?” Well, the Amaretto Sour is a whiskey drink, or at least, it should be. It’s been 10 years since a bartender named Jeffrey Morgenthaler wrote on his blog that he had derived “the best Amaretto Sour in the world,” and it was the shake heard round the world. Morgenthaler’s version—amaretto and lemon, punched up with a pour of high-proof bourbon, and smoothed out with an egg white—utterly transforms the drink. “It’s difficult to overstate how many favors the addition of high-proof bourbon does for the Amaretto Sour,” we write, “it’s not a revision so much as it is born again.”

Add all ingredients to a cocktail shaker and shake without ice for five to seven seconds to whip the egg white. Add ice and shake hard for eight to 10 seconds. Strain either over fresh ice in a large rocks glass or up in a coupe. Garnish with a lemon peel and, if you like, a cherry.

Don’t be fooled by the Mint Julep. Its campaign materials may have you convinced it’s just a harmless little minty refresher, but in reality it’s nearly a double-pour of bourbon, tempered only by mint and a touch of sugar. Nonetheless, some 120,000 Mint Juleps are consumed across two sunny days at Churchill Downs during the Kentucky Derby, proving that some cocktails can become refreshing daytime summer sippers just by sheer force of will, and a little crushed ice. Find out the best bourbon to use for your Mint Julep here, or if the race is about to start, quickly fix one up according to the recipe below.

In a metal cup, gently muddle the mint into the simple syrup. Add bourbon and fill 2/3 with crushed ice. Stir to chill, until a frost forms on the outside. Then pack the rest of the cup with ice. Take two mint crowns, lightly bruise them with your fingers, and stick them against the inside close to the straw. Enjoy.