11 Of The Best Bourbon Cocktails

11 Of The Best Bourbon Cocktails

Bourbon has been the backbone of American cocktail culture for well over a century, long before craft mixology became a cultural phenomenon. The golden age of cocktails — stretching from the mid-1800s through Prohibition and into the mid-20th century — gave us some of the most enduring drinks ever conceived, many of which were built squarely around the rich, caramel-and-oak character of American whiskey. What makes these classic recipes so compelling is their simplicity: a handful of quality ingredients, a little technique, and a good pour of bourbon do most of the heavy lifting. Whether you're a seasoned home bartender or just beginning to explore what bourbon can do beyond the glass, these time-tested cocktails are a masterclass in why some things never go out of style.

Knob Creek Old Fashioned: Pre-Prohibition Power in a Glass

The Old Fashioned is widely regarded as the first cocktail ever recorded, with roots stretching back to the early 1800s when drinkers would order an 'old-fashioned whiskey cocktail' to distinguish it from flashier, over-garnished drinks of the era. Knob Creek Small Batch is a natural match — bottled at 100 proof and described as a 'full proof for full flavor, an honest Pre-Prohibition style bourbon,' it delivers bold caramel, oak, and vanilla that hold up beautifully against bitters and a sugar cube. Its higher ABV means the spirit doesn't get lost once stirred with ice, keeping the drink spirit-forward and true to its roots. The classic recipe is almost deceptively simple: muddle a sugar cube with Angostura bitters, add the bourbon, stir over a large ice cube, and finish with an expressed orange peel. Few cocktails reward a quality pour more than this one — the whiskey is the drink.

Woodford Reserve Mint Julep: Kentucky Derby's Definitive Sip

The Mint Julep was invented in the late 1700s and has been the official drink of the Kentucky Derby since 1939, with nearly 120,000 served over a single Derby weekend. Woodford Reserve is the presenting sponsor of the Kentucky Derby, making it more than a fitting choice — it is the cocktail's most iconic commercial partner. Bottled at just over 90 proof, Woodford brings smooth notes of vanilla, honey, and gentle spice that balance perfectly against fresh mint and simple syrup without overwhelming them. The drink is built directly in a chilled silver or pewter julep cup: gently muddle mint with syrup, pack with crushed ice, pour bourbon, and stir vigorously until the outside of the cup frosts over. The result is icy, aromatic, and perfectly sweet — summer in a glass.

Four Roses Whiskey Sour: Citrus-Forward and Classically Balanced

The Whiskey Sour is one of the oldest American cocktails, with the earliest known mention by name appearing in an 1870 Wisconsin newspaper — and it has been a bartender's staple ever since. Four Roses Small Batch is a smart choice for this cocktail, bringing what experts describe as nuance beyond classical sweet and earthy notes, thanks to the brand's unique approach of blending multiple mash bills into a single bottle. The result is a bourbon with elegant spice and fruit-forward complexity that cuts beautifully through fresh lemon juice without overpowering the delicate balance of sweet and sour. Shake Four Roses with fresh lemon juice, simple syrup, and an optional egg white for a silkier texture, then strain over ice into a rocks glass and garnish with a cherry and orange slice. Adding an egg white gives the drink a velvety foam and elevates a humble classic into something genuinely elegant.

New Riff Manhattan: Craft Bourbon Meets a 19th-Century Classic

The Manhattan is one of the most enduring cocktails in American history, with the earliest published recipe dating to 1882 and the drink traditionally believed to have been created at New York's Manhattan Club. New Riff Bottled-in-Bond from Newport, Kentucky is a craft bourbon that has already built a strong reputation since the distillery opened its doors — bottled at 100 proof with a high-rye mash bill, it delivers rich fruit, caramel, and spice that stand up beautifully to sweet vermouth and bitters. The Bottled-in-Bond designation guarantees the whiskey is the product of a single distillation season and at least four years of aging, lending it the kind of authenticity that suits a cocktail this storied. Stir two parts New Riff with one part sweet vermouth and a couple dashes of Angostura bitters until well chilled, then strain into a coupe and garnish with a Luxardo cherry. The high-rye character keeps the drink from tipping too sweet, a common pitfall when bourbon replaces rye in this classic recipe.

Wild Turkey 101 Smash: A Centuries-Old Muddled Classic Revived

The Whiskey Smash has been one of the great whiskey drinks for hundreds of years, though it fell out of fashion in the early 20th century before staging a comeback on the back of the modern bourbon boom. It is essentially a citrusy, minty upgrade to the Mint Julep — muddled lemon wedges and mint leaves combined with bourbon and simple syrup, shaken and strained over crushed ice. Wild Turkey 101, aged six to eight years and bottled at its signature 101 proof, has been made the same way for over 60 years, giving it a backbone of vanilla, toffee, and baking spice that stands up confidently to the brightness of fresh citrus and muddled herbs. The higher proof is key here: it ensures the spirit remains a major player even after shaking and dilution, keeping the drink lively rather than flat. For around $25, this is one of the most authentic and affordable pairings in the old-school cocktail canon.

Elijah Craig Hot Toddy: Heaven Hill's Winter Warmer Done Right

The Hot Toddy is a whiskey cocktail with ancient roots — a warm, soothing blend of whiskey, honey, lemon, and hot water that has doubled as a cold-weather home remedy for generations. Elijah Craig Small Batch from Heaven Hill is a well-regarded choice for this drink, with expert bartenders selecting it specifically for build-your-own hot toddy programs thanks to its rich profile of toasted oak, caramel, and warm baking spices. Named after the Baptist preacher credited with first aging whiskey in charred oak barrels, Elijah Craig leans into an oak-forward style that gives the Hot Toddy depth and complexity beyond the basic spirit-and-citrus formula. The recipe is simple: combine two ounces of bourbon with a tablespoon of pure honey and a squeeze of lemon in a heatproof mug, then fill with hot water and optionally add a cinnamon stick or a few cloves for spice. The result is warming, fragrant, and deeply comforting — a drink that belongs as much to cold, quiet nights as it does to the cocktail menu.

Old Forester Boulevardier: A Prohibition-Era Bourbon Negroni

The Boulevardier was born in the Prohibition era, invented by Erskine Gwynne — the nephew of railroad tycoon Alfred Vanderbilt — and named after Gwynne's Parisian expatriate magazine; it is effectively a Negroni built with bourbon instead of gin, combining the spirit with sweet vermouth and Campari. Old Forester 100 Proof, one of America's oldest continuously produced bourbon brands dating back to 1870, brings a rich, complex profile of cherry, vanilla, and baking spice that complements the bitter-orange character of Campari with remarkable precision. Bottled at 50% ABV, it delivers enough strength to stay bold when stirred with ice, and its history gives it the kind of old-school credibility the cocktail demands. The standard build is equal parts or a 3:2:2 ratio of bourbon, sweet vermouth, and Campari, stirred with ice and strained over a large cube with an orange zest twist. The sweetness of the bourbon rounds out the drink where gin's botanicals would create a more angular finish.

Bulleit Bourbon Mule: High-Rye Kick Meets the Copper Cup

The Kentucky Mule is a straightforward riff on the Moscow Mule — swapping vodka for bourbon and adding a distinctly Southern character to the familiar trio of spirit, ginger beer, and lime juice. Bulleit Bourbon is a nationally recognized high-rye bourbon, and its spicier-than-average profile adds what experts describe as an interesting twist to mixed drinks, cutting through the heat of ginger beer with a bold, dry edge rather than a sweet, soft one. Its mash bill runs significantly higher in rye than most Kentucky bourbons, giving it forward notes of pepper and baking spice alongside the expected vanilla and oak. Build the drink directly in a copper mug: fill with ice, add two ounces of Bulleit, top with ginger beer, and squeeze in half a lime before garnishing with a mint sprig and lime wheel. The spice-on-spice combination of a high-rye bourbon and ginger beer creates a mule that is considerably more assertive and refreshing than its vodka-based cousin.

Michter's Seelbach: Louisville's Sparkling Forgotten Gem

The Seelbach Cocktail is named after the historic Seelbach Hotel in Louisville, Kentucky, and is one of the most overlooked old-school bourbon drinks — a festive sparkling cocktail built with bourbon, Cointreau, Angostura bitters, Peychaud's bitters, and topped with Champagne. Michter's US*1 Small Batch is a premium choice here, earning praise from bartenders for its perfect balance of age, proof, spice, fruit, and softness that upholds both classic and modern cocktail formats. Its gentle notes of caramel and vanilla provide the sweet base that integrates effortlessly into the Cointreau and the bubbles without being buried by them. The method is precise: combine bourbon with Cointreau and seven dashes each of Angostura and Peychaud's bitters in a Champagne flute, then top with cold bubbly and garnish with an orange twist and cherry. The result is a bourbon cocktail with genuine elegance — less known than a Manhattan but every bit as sophisticated.

Brown Derby: Hollywood's Golden Age Bourbon Cocktail Survives

The Brown Derby dates to the 1930s and is said to have been created by a bartender at the Vendôme Café on Sunset Boulevard in Los Angeles — owned by Hollywood Reporter founder Billy Wilkerson — then named after the nearby Brown Derby restaurant, a social hub for Hollywood's elite during the golden age of film. The drink is built with bourbon, fresh grapefruit juice, and a sweetener — traditionally maple syrup, though honey syrup creates what some refer to as the related De Rigueur variant. Elijah Craig Small Batch has been recommended specifically for this cocktail at real bar programs, bringing its oak-forward warmth and dark caramel notes to balance the bitter tang of grapefruit without overwhelming the citrus. Like a Whiskey Sour, it uses citrus juice to bring a sour note, but grapefruit delivers a more complex, slightly bitter edge rather than sharp lemon tartness. Shake all three ingredients with ice and strain into a chilled coupe with a grapefruit twist — it is bright, refreshing, and unmistakably retro.

Maker's Mark Paper Plane: The Modern Equal-Parts Classic

The Paper Plane was created by bartender Sam Ross in 2007 at New York City's Milk & Honey, riffing on the equal-parts structure of the Last Word by swapping gin for bourbon and maraschino for Aperol. Built from equal measures of bourbon, Aperol, Amaro Nonino, and fresh lemon juice, the drink achieves a precise balance of bitter, sweet, and sour that has made it one of the defining cocktails of the modern era. Maker's Mark is a natural fit here: the Loretto, Kentucky distillery swaps rye for soft red winter wheat in its mash bill, producing a wheated bourbon whose caramel sweetness and gentle texture keep the cocktail from tipping into harshness. The Aperol brightens those signature caramel notes while the herbal depth of Amaro Nonino adds complexity that a sharper, rye-forward bourbon might overpower. Shaken hard and double-strained into a coupe, it's a cocktail that rewards precision — much like the paper airplane it's named after.

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