The past few weeks I’ve been blessed to have time off from my usual vocation allowing me more time for my avocation: drinking, I’m still thinking about bourbon.
I’d written last time that bourbon was America’s one truly unique offering to the world of spirits, so it makes sense to explore more in-depth the brief story of the cocktail and how it almost uniquely derives from America’s unique liquor.
Bourbon is a favorite among many who like to drink spirits. This in-depth guide highlights the “best of the best” bourbon cocktails (along with recipes), whether for its place in history, taste, prestige, versatility or overall delight it brings. This roundup is intended to show that there’s drink for every whiskey lover.
Subscribe to The Gentleman Within Podcast.
The Cocktail’s Origins
The word “cocktail” itself is uniquely American (appearing in an 1803 print of the Farmer’s Cabinet, although there is some debate that the drink wasn’t meant as an exclusively alcoholic one until 1806; the details are now lost to time) and as such pairs well with our spirit of choice to make delicious simple bourbon cocktails.
The Prohibition Era
Things really took off, however, during the ratification of the 18th Amendment and the Volstead Act, more commonly referred to as Prohibition (what is really fascinating is that Americans could simply say “Prohibition” and the referent was so clear that no one needed to ask what was being prohibited!).
Funnily enough, Prohibition caused a surge in drinking liquor while a drastic culling of the wine and beer industry took place. Among the other side effects, some bourbons were declared medicinal and allowed to be produced throughout. A negative side effect, however, was that some of the bootleg bourbon being produced was so foul it needed quite a lot of help to make it palatable.
Enter: the cocktail.
» Related: You might enjoy this article on the Best Bourbon Brands Under $100.
Best Bourbon Cocktails
And now let’s get into the 7 classic bourbon cocktails starting with the OG.
1. Old Fashioned
The oldest bourbon cocktail comes from this period: the Old Fashioned. Originally called a “cocktail,” as it was about the only one you’d get, so further clarification wasn’t needed, it was later called an “old fashioned cocktail” as more were added to the menus and this was pushed further into the past.
The recipe is based around a simple idea: make the bourbon (which might not have been the nicest) taste better. You add a little water, sugar, bitters, cherry, and citrus to your bourbon and serve with a small amount of ice. The water cuts down on the cask strength bourbon available more commonly at the time and the sugar and citrus help lift some of the darker notes while the bitters round out the taste experience.
In this way, it’s basically a perfect cocktail, however a great many places I’ve been to struggle with the historic and foundational item.
Old Fashioned Recipe
The foundational recipe and one every person should be able to mix. Tastes thin, edgy, spikey and should only be used with a bourbon you can drink on its own. Avoid inexpensive options as this drink leaves no cover and will expose you immediately.
- 1 Sugar cube
- 4-5 Shakes of Bitters (Angostura is fine, I prefer Peychaud’s – feel free to experiment!)
- Orange peel
- Luxardo cherry (optional)
- 2-3 ounces of Bourbon
- Glass: old fashioned; rock’s glass; lowball (all different names for the same glass – a lot of places use / sell double old fashioned glasses [DOF glasses] which are the same but predictably larger)
1. Add one sugar cube (loose sugar is fine, approximate one light teaspoon) and douse with four or five shakes of bitters. This should saturate the sugar cube. Add a small orange slice. Muddle until the sugar and orange are nicely mixed – the sugar should half dissolve into something like a paste. Splash a little water in, add ice, pour 2-3 ounces of bourbon on top, stir.
2. Garnish with the luxardo cherry if you choose and an orange peel. If using the orange peel, twist it to release some of the oils and then rub it around the rim of the glass to give an enhanced orange experience.
From here we develop the old fashioned’s slightly more posh descendant: the Manhattan. The Manhattan is more or less the same except turned into a form resembling a martini.
Consisting instead of whisky, vermouth, cherry, and bitters, the vermouth is expected to do the work of the citrus and sugar in lifting a less palatable whisky to a delicious cocktail. In my experience, most Manhattans have a more syrup-like quality than the thin and edgy taste of an old fashioned.
However, Manhattans are served in a cocktail glass which can make people feel more elegant for some reason – it more practically has the advantage of letting you know when you’ve been over served as you will find a suspicious amount of the drink occupying your hands instead of its proper place in the glass.
Now available just about everywhere after a cocktail resurgence over the past few decades, the Manhattan can make you feel like you’re in the Big Apple with its smooth and luxurious taste profile with just a hint of spike from the vermouth. Use a quality bourbon for this but there is a little more cover than the Old Fashioned. Many places use Maker’s Mark which is perfectly adequate.
- 1 part Sweet red vermouth
- 3-5 dashes of Bitters (same as before)
- Luxardo cherry (or similar brandied cherry)
- 2 parts Bourbon
- Glass: cocktail glass
1. Add a two-to-one ratio of bourbon to vermouth into a cocktail shaker with ice. Dash about 3-5 dashes of bitters into this. Add a spoon of the brandied cherry juice if you like your drinks a little sweeter or if you’re using a higher octane bourbon. Shake until cold.
2. Strain into a chilled cocktail glass, garnish with the cherry.
Jumping sideways a bit, we come to another classic simple bourbon cocktail: the Boulevardier. A much less common, but no less delicious, variation of the Manhattan, this drink is something like a Manhattan getting together with a negroni (a delicious gin cocktail but one not covered here).
It is composed of bourbon, vermouth, and campari. Some recipes have this served in the older style like an old fashioned (on the rocks with a citrus garnish) but you can often find it shaken and poured into a cocktail glass more like a Manhattan.
It’s rich, smooth, has some spice notes, simple to make, and just uncommon enough you’ll be very impressive when you bust this out at your next drinks party.
The discrete cousin of the Manhattan and Negroni, this drink combines the taste profile of an Old Fashioned and Manhattan to give you something sweet and smooth but thinner and much more bitter (thanks to the Campari) than either. You can get away with a less expensive bourbon here since it’s only half of the drink.
1 part Sweet vermouth
1 part Campari
2 parts Bourbon
Garnish: orange peel
Glass: old fashioned
1. Add all ingredients to a cocktail shaker with ice and shake until cold. I use 2:1:1 instead of the more common 1.5:1:1 as I think it balances better, but adjust based on your bourbon choice.
2. Strain into the glass with regular ice, garnish with an orange peel.
4. Whiskey Sour
Finishing with the heavier, more cherry-like cocktails and moving into the zesty and lighter options, our first stop should be a Whisky Sour. A whisky sour is one of the best known shaken bourbon cocktails and is comprised of quite simply: bourbon, simple syrup, lemon juice, and garnished with citrus peel.
This gives a drink that, counter to the heavier Manhattan, is light and refreshing thanks to the work of the lemon juice and is an excellent companion all year round.
Whisky Sour Recipe
Alternatingly sweet and sour, this is a perfect drink before dinner and won’t bog you down like a Manhattan might on a summer day. Tastes crisp and fresh thanks to the lemon and sugar and in a cold glass can be like a whisky lemonade on a hot day.
- Brandied cherry (maraschino is fine for this one)
- 3 parts bourbon
- 2 parts lemon juice
- 1 part simple syrup (50:50 ratio of sugar and hot water allowed to dissolve together and cool. You
- can make a batch of this and leave in a sealed container in the refrigerator chilled for about a week)
- Glass: chilled old fashioned glass, served up or on the rocks (with or without ice).
1. Add the three liquids to a cocktail shaker and shake until chilled. Strain into chilled glass.
2. Garnish with a half slice of orange and cherry; classically these are speared on the little plastic picks but can also be left to float around, as you desire.
Quick note: If you’re enjoying this guide on best bourbon brands under $100, then you’ll probably find my other writing on all things style, self-development & drinks useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.
To join now, just enter your email address below and click “Get Updates!”
5. Mint Julep
Moving on to other frothy, icy things, we have what comes in as an absolute classic and arguably DC native: the Mint Julep. Definitely a favorite of the Kentucky Derby, it is claimed that the mint julep was invented in the Round Robin bar of the Willard InterContinental hotel by Senator Henry Clay sometime after the historic hotel opened in 1847.
They are one of the few places where you can find a mint julep year round and enjoy it under a large portrait of the Senator – a visit to this hotel’s bar is strongly recommended.
The drink itself, whether there or deliciously homemade, is comprised of mint leaves, simple syrup, bourbon, and poured over crushed ice. A classic.
Mint Julep Recipe
A Kentucky classic descended from DC, this is a fresh and charming addition to a summer ensemble or to mint fanatics anywhere. Although the silver julep cup is fun, for beginning bartenders don’t worry about using a highball. The taste is something like a simple bourbon based mojito and can be made by the pitcher to serve at a summer grill out.
- Handful of mint leaves
- 1 part simple syrup
- 6 parts bourbon
- Crushed ice
- Garnish: more mint leaves
- Glass: traditionally a silver julep cup; modernly this can also be a highball or collins glass (the tall, skinny kind)
1. Lightly press (don’t smash or muddle!) the mint against the inside of the cup – they can also be firmly slapped against the back of the hand and tossed into the chilled empty cup and rolled around for a similar effect. You will immediately smell the mint oil release. Add the simple syrup and then fill with ice.
2. Pour the bourbon over the ice and stir it until frost begins to form on the outside of the cup. Garnish with a mint sprig (or skip if you’re not as fancy). Serve with a small straw to balance out the crushed ice.
3. NB: don’t use small mint leaves or in any way chop them up as you’ll be fishing mint leaves from your teeth the rest of the evening!
» Related: You might enjoy this guide on Jack Daniel’s vs Jim Beam vs. Johnnie Walker.
6. Bourbon Smash
The mint julep’s cousin has to be the Bourbon Smash, and a particular favorite of mine, often after I’ve already had one or five. There is some debate over the “proper” recipe so I’ll give the one I like more but they are almost the same.
A bourbon smash is much like a mint julep but with around 4 small wedges of lemon that get muddled along. I prefer, however, to use lightly bruised basil leaves instead of what some argue for: mint.
The mint version of the smash was undoubtedly around by the 1880s and shows how it only takes a few decades for a drink to have earned its own name and branched away from its antecedent, the julep.
Bourbon Smash Recipe
Icy and fresh, this is my version of drinking a salad. Inexplicably refreshing, this is a go to after a few drinks as it feels like you’re not drinking as much (you still very much are). I like this year-round, even in the dead cold as the basil is ever-refreshing to me. Honestly, I usually have this with Chinese take-away. I don’t know why, but there’s my recommendation.
- 3-4 lemon wedges (three big, four if they’re small)
- 3-4 parts bourbon
- 1 part simple syrup
- Basil (I strongly prefer) or mint
- Garnish: basil or mint leaf
- Glass: old fashioned
1. Muddle the lemon wedges in the shaker. If you don’t have simple syrup you can get away with using sugar at this point but it will come out a little grainy in the end.
2. To this add bourbon, the simple syrup, whole basil leaves or mint, and ice. Shake until well chilled. Double strain into chilled glass. (The double straining gets all of the tiny leaf particles that inevitably are created by shaking. The fewer bits you want in your teeth, the more carefully this should be done.)
3. Garnish with a sprig of basil or mint, as you choose.
And finally, one of my absolute favorites that I almost never drink: the sazerac. This historic drink comes from New Orleans and was either invented by Aaron Bird at the Sazerac Coffee House (as of 2019, a museum) or by a local Creole chemist.
The name Sazerac comes from a brand of cognac used in the original recipe: Sazerac-de-Forge et Fils. After a devastating illness plagued most of France’s grape crops in the late 1800s, bourbon became the liquor of choice for this cocktail and has remained so since.
It is spicely flavored with absinthe, something I grew up thinking had a vague and dangerous reputation as somehow edgier and inexplicably poisonous (a smear campaign, it turns out, which lead to it being banned in the US in 1912 – it is again available but the reputation hasn’t fully recovered).
A sazerac is much like an old fashioned, since almost every bourbon cocktail takes its foundation from it, but is simply a sugar cube, bourbon, absinth, and bitters.
Arguably, the other founder of the sazerac is the aforementioned chemist. You see, Aaron Bird used the bitter from his local supplier, one Antoine Amedie Peychaud. The very same who gives us Peychaud’s bitters today (and my favorite, over the slightly more common but to me not as good Angostura bitters).
It is said that he originally invented this drink and that Aaron Bird gets the credit since he ran the bar that put this on the menu. We cannot know for sure but it also wouldn’t surprise me that a slightly more obscure Creole person would be swept aside by the more prominently placed “mainstream” bar owner in the attribution. When you make your sazeracs at home, be sure to use Peychaud’s as a tribute to its possible creator.
The most complicated of the lot due to the rinse stage but it also gives the most complicated flavor. There are also many people inexplicably impressed when you break out the absinthe. The taste is spicy, anise-like, with just a hint of sweet citrus.
Much like an Old Fashioned, you cannot hide behind cheap bourbon here. Aim for a bourbon that is higher on the spicy scale instead of sweet and you’ll really have a drink that people will remember. This can be served in a cocktail glass as well but the old fashioned is the more traditional option.
- 5 parts bourbon
- 1 part absinthe
- Sugar cube
- 2-3 dashes of Peychaud’s bitters
- Garnish: lemon peel
- Glass: chilled old fashioned glass
1. Get your glass very cold and then rinse it with the absinthe. Add crushed ice and set this aside.
In a cocktail shaker, muddle the sugar cube with the bitters, add ice, pour over the bourbon. Stir (not shake) until very chilled.
2. Go back to the glass and pour out the ice and absinthe. Let any extra absinthe be poured out with the ice but leave what clings to the walls of the glass. To this, strain the mixture in the cocktail shaker. Garnish with a lemon peel.
Whiskey Book Recommendations
- A Field Guide to Whisky: An Expert Compendium
- Whiskey Master Class: The Ultimate Guide
- The Bourbon Bible: The Complete Low-Down
- Bourbon: The Rise, Fall and Rebirth of an American Whiskey
- American History Through a Whiskey Glass
- Whiskey: A Tasting Course ( A new way to Think and Drink Whiskey)
- The World Atlas of Whisky
Wrapping Things Up
Whether you enjoy your bourbon as a simple old fashioned, or get creative with flavored bitters, these foundational bourbon recipes will give you all of the hallmarks of quality options for you and any guests you might entertain.
I’ve given my preferred ratio and stylings for all of these drinks but feel free to tweak them to suit the bourbon you’re using or your own preferences.
Once upon a time I got these recipes from various places and people and have changed them to suit my needs (like the strong preference for luxardo cherries instead of maraschino) and you’ll find yourself changing them as well.
Enjoy, explore, and dive into these simple bourbon recipes and above all, have responsible fun.
Elijah C. Mills is a native of Indiana, but now resides in Washington, D.C. A lover of all things ethanol and bow ties, you can find him out and about at various D.C. events. He is an active Episcopalian and works as a Parish Administrator at a DC Episcopal church. He’s always happy to meet over a drink and can be easily talked into most social events.
What is your go-to bourbon drink?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community. Looking forward to seeing you in there.
LIKE WHAT YOU READ?
Get more posts like this plus style tips & advice delivered straight to your inbox.