A good bourbon cocktail is mostly a matter of proportion and a little patience. The classics below have lasted because they're built right — each one balances the sweetness, spice, and oak of bourbon against acid, bitterness, or dilution in a way that makes the whiskey taste better, not buried.
Every recipe here lists exact measurements and tells you whether to stir or shake. Make them once as written, then adjust to your taste. None of them require a liqueur you'll use once and abandon, and most come together in under two minutes.
Before You Start: Bourbon, Ice, and Glassware
Three things separate a good home cocktail from a watery one.
The bourbon matters most. In a cocktail with two or three ingredients, the whiskey is the drink. Reach for something you'd sip neat. For spirit-forward drinks, our Straight Bourbon is rye-forward with the backbone to stand up to vermouth and bitters. For anything with citrus, the softer profile of Bud & Dewey's Wheated Bourbon folds in cleanly. If you want a smoky twist on an Old Fashioned, our Smoked Straight Bourbon does the work for you.
Use real ice. Big, cold, fresh cubes melt slowly and dilute less. The small, half-melted cubes from the back of the freezer water your drink down fast. For drinks served "up," you still chill with ice and strain it out.
Chill the glass. Stick your coupe or rocks glass in the freezer for a few minutes before you build. A cold glass keeps the drink colder longer, which matters more than any garnish.
Make Your Own Simple Syrup
Several recipes below call for simple syrup, and it takes two minutes to make. Combine equal parts sugar and water — say, half a cup of each — and stir over low heat until the sugar dissolves, or just shake them together in a jar until clear. Let it cool and keep it in the fridge, where it holds for about a month. For honey syrup, do the same with honey and warm water at a 1:1 ratio. Buying pre-made syrup works, but homemade is cheaper and tastes cleaner, and you control the sweetness.
The Old Fashioned
The oldest cocktail formula there is: spirit, sugar, bitters, water. Get this one right and the rest follow.
- 2 oz bourbon
- 1 sugar cube (or ¼ oz simple syrup)
- 2–3 dashes Angostura bitters
- Orange peel
Add the sugar cube to a rocks glass, soak it with the bitters and a small splash of water, and muddle until mostly dissolved. Add the bourbon and one large ice cube. Stir for about 20 seconds. Express an orange peel over the top — squeeze it skin-side down to spray the oils — and drop it in.
Bitters aren't optional. They're what separate an Old Fashioned from sweetened whiskey. A bottle of Angostura is a few dollars and lasts years.
The Manhattan
The Old Fashioned's more sophisticated cousin. Swap the sugar for sweet vermouth and you get a drink with wine-like depth.
- 2 oz bourbon
- 1 oz sweet vermouth
- 2 dashes Angostura bitters
- Brandied cherry
Stir all the liquid ingredients with ice in a mixing glass for 20–30 seconds, then strain into a chilled coupe. Garnish with a cherry. Keep your vermouth in the fridge after opening — it's wine, and it goes flat and sour within a month or two at room temperature.
A Manhattan is traditionally made with rye for extra spice, but bourbon makes it rounder and a touch sweeter. Both are correct.
The Whiskey Sour
The gateway sour, and the drink that proves bourbon and citrus belong together.
- 2 oz bourbon
- ¾ oz fresh lemon juice
- ¾ oz simple syrup
Shake hard with ice for 10–15 seconds and strain over fresh ice in a rocks glass. Fresh lemon juice is non-negotiable — the bottled stuff tastes flat and slightly metallic.
The Egg White Version
For a silky, foamed top, add ½ oz egg white (or aquafaba for a vegan version) and do a "dry shake" first: shake everything without ice for 10 seconds to build the foam, then add ice and shake again to chill. Strain into a coupe. The egg adds texture, not flavor.
The Boulevardier
A Negroni built on bourbon instead of gin. Bitter, balanced, and a great after-dinner drink.
- 1½ oz bourbon
- 1 oz Campari
- 1 oz sweet vermouth
Stir with ice and strain over a large cube in a rocks glass, or serve up in a coupe. Garnish with an orange peel. The Campari brings the bitterness; the bourbon's sweetness and the vermouth round it off. If it's too bitter for you, bump the bourbon to 2 oz.
The Mint Julep
The Kentucky classic, and a reminder that bourbon shines in hot weather too.
- 2½ oz bourbon
- ¼ oz simple syrup (or 1 tsp sugar)
- 8–10 fresh mint leaves
- Crushed ice
Gently press the mint and syrup in the bottom of a cup — don't shred the leaves, just bruise them to release the oil. Fill with crushed ice, add the bourbon, and stir until the cup frosts over. Top with more crushed ice and a big mint bouquet. Traditionally served in a metal julep cup, which frosts beautifully, but any glass works.
Three More Worth Knowing
Once the classics feel easy, these three round out a home repertoire.
Gold Rush
A three-ingredient sour that swaps simple syrup for honey. Shake 2 oz bourbon, ¾ oz lemon juice, and ¾ oz honey syrup (honey cut 1:1 with warm water) over ice; strain over fresh ice. Rich, bright, and dead simple.
Bourbon Smash
Halfway between a Julep and a Sour. Muddle a few lemon wedges and mint with ½ oz simple syrup, add 2 oz bourbon, shake with ice, and pour unstrained into a rocks glass. Rustic and refreshing.
Paper Plane
A modern classic in equal parts: ¾ oz each of bourbon, Aperol, Amaro Nonino, and fresh lemon juice. Shake and strain into a coupe. Bittersweet and citrusy — worth the extra bottles if you like the bitter end of the spectrum.
Stirred vs. Shaken: The One Rule to Remember
When you're not sure how to finish a drink, this rule covers almost every bourbon cocktail: stir drinks that are all spirit, shake drinks with citrus or egg.
Stirring chills and dilutes gently while keeping the drink silky and clear — right for the Old Fashioned, Manhattan, and Boulevardier. Shaking aerates and chills fast, which sours and anything with egg white need to come together. Shake an all-spirit drink and you'll get a cloudy, over-diluted result; stir a sour and it'll taste flat and warm. That's the whole science of it.
If you'd rather start even simpler, our guide to easy 2-3 ingredient bourbon drinks covers the no-shaker end of the spectrum. And if you want to understand what makes a bourbon a bourbon in the first place — the 51% corn minimum, the new charred oak, the proof rules — the TTB's distilled spirits product categories lay out the federal standards. For the canonical specs on the classics above, the International Bartenders Association's official cocktail list is a reliable reference.
The best way to learn these is to make them. Pour a good bourbon, measure carefully the first time, and taste as you go. Want to taste ours before you stock the bar? Come book a tour and tasting at our Marquette distillery and try the bourbons these recipes were written for.