25 Best Bourbon Cocktails Of All Time Ranked From Worst To Best

During the 15th and 16th centuries, the first settlers in the U.S., particularly the Irish and Scottish, desperately missed their whiskey and sought to recreate it in their new home (via Whisky.com). The first rural distilleries were built in Maryland, Pennsylvania, and Virginia. Most theorize that bourbon was named after Bourbon County, though Kentucky bourbon expert Michael Veach posits that it was named after the New Orleans entertainment district, Bourbon Street, per Smithsonian Magazine. Yet, while the origins and creators of bourbon remain vague, the rules surrounding bourbon production are quite clear. 

The making of bourbon must follow a stringent process; the mash, which is the blend of grains that the bourbon is based on, must contain at least 51% corn (via World Whisky Day). Also, distillation must take place at no more than 160 proof and the distillate should be stored in oak barrels at no more than 125 proof. So while every bourbon is a type of whiskey, not every whiskey can call itself bourbon. 

Today, 95% of the world's bourbon is made in Kentucky (via CNBC). It's a distinctly American spirit that's perfect to sip neat or mix into cocktails. That being said, some cocktails really bring out the complex flavors of bourbon, while others are wishy-washy and simply don't do this spirit any justice.

Bourbon and summertime lounging don't exactly go hand in hand (although you might feel differently by the time you reach the end of this list). So the sour sunrise cocktail seems like an interesting drink, to say the least. The drink is a take on the tequila sunrise: It's made with bourbon, freshly squeezed lemon juice, freshly squeezed orange juice, simple syrup, and grenadine. This fruity, boozy cocktail is ideal for brunch. 

While it's a delicious summer sipper, it's not quite as balanced as some of the other cocktails on this list. This cocktail lacks depth and falls a little flat on the palate. The sour sunrise is perfect for instances when you don't want to think too much about what you're drinking. The drink has a beautiful ombré color, which makes it perfect for posting on social media. But if you're looking for a bourbon drink with which to wow your snooty spirits aficionado acquaintance, this definitely isn't it.

Here's another summertime sipper. Sure, this cocktail is partially redeemed by the fact that grapefruit is an all-around universal match with many spirits. But before you get too excited, we should warn you: The grapefruit bourbon smash is in dire need of some herbal or aromatic qualities, so you'll often see it served with rosemary or other herbs. The Health.com recipe calls for orange marmalade, which also tempers the sour notes in the grapefruit.

However, grapefruit and bourbon don't complement each other the way, say, tequila and grapefruit do. Bourbon needs a partner with more oomph and grapefruit doesn't want to be bogged down with bourbon's intensity — it's a fundamentally ill-suited combination. Bourbon and grapefruit work well separately, just not as a collective unit. That doesn't mean it's a horrible drink, but in the grand scheme of bourbon-based cocktail options, you'd be hard-pressed to find a less impressive combo.

Bourbon, lime juice, allspice dram, bitters, and simple syrup walk into a bar ... there's no punchline here because there's no reason these ingredients would all be in the same room, right? Unless of course, they all met in a Lion's Tail cocktail. This wants to be a stellar cocktail. It's practically begging for it. According to Serious Eats, this drink is made by combining bourbon, allspice, and bitters in a shaker, adding ice, and straining into a cocktail glass. 

Unfortunately, somewhere along the flavor path, the lime juice throws it all off. It's drinkable enough, but it lacks the coziness, warmth, and comfort of some other bourbon cocktails. The Lions Tail gets points for creativity and intrigue. When you take a sip of Lion's Tail, you're interested enough to take another. But ultimately, it doesn't come together like some of the other well-loved classics. The Lion's Tail gets an E for effort. 

The Belmont Jewel is a summer racetrack drink that contains bourbon, lemonade, pomegranate juice, and orange zest (via Sports Illustrated). While summer racetrack drink is not an official cocktail category, we think it's an apt title for the Belmont Jewel. The Belmont Jewel is the official drink of the Belmont Stakes race that takes place in Elmont, New York. 

The Belmont Jewel became the signature cocktail of the race in 2011 and has been a hit with attendees since. The drink has a lot of promise. It contains key components that make up a perfectly balanced cocktail: The depth of the bourbon is paired with the sweet acidity of the fruit. That being said, it's not a terribly interesting drink, though it is refreshing. Its fruity simplicity makes it ideal for horse races and the warmer months. This cocktail shouldn't be judged too harshly, though, especially because it's pleasant and is perfect for certain sports-based scenarios.

If you transport yourself back to the grade in which you read "To Kill a Mockingbird" by Harper Lee, you probably remember the Finch family, central to the novel's plot. You might also remember the character of Boo Radley, the Finch family's neighbor. This is where the cocktail gets its name. 

According to Punch, the Boo Radley cocktail was created by Chris Hannah, the former bartender at Arnaud's French 75 bar, who tweaked the recipe for a Southern cocktail. The Boo Radley drink calls for bourbon, Cynar, cherry liqueur, garnished with lemon and orange peels. It's a roller coaster for the palate that starts off bourbon heavy and then glides into the herbal Cynar notes and finishes with some sweet cherry. 

This drink has an impressive balance and a nice weaving of flavors, but because it's a heavier, richer drink it's not something you'll reach for every Friday evening. This beverage is interesting enough to serve on special occasions or for at-home entertaining. However, if you don't keep a fully stocked bar, you might have to run to the store for supplies the first time you make this.

Is it even a party if you don't have punch? Just add some bourbon to elevate your punch from college dormitory jungle juice to an impressive adult concoction. According to Difford's Guide, the first written reference to punch dates back to 1632. Back then, the recipe for punch contained rosewater, sugar, and juice. 

The best aspect of punch is that it doesn't require much precision to taste good. According to Liquor.com, the super Sunday punch blends together cloves, allspice, apple brandy, grapefruit juice, honey, sweet tea, and, of course, bourbon. You can also bring out more delicate, herbal notes in the punch by adding some rosemary. Bourbon punch is the ultimate cocktail, one that is perfect for parties or just lazy afternoons at home. 

Bourbon punch is great because it can be as simple or as extravagant as you like. However, it's not going to win you any mixologist of the year awards. Punch lacks depth and complexity of flavor. Any attempts to make it interesting might just result in the flavor becoming more muddled. 

If you're looking for a juicy, bourbon-forward cocktail, look no further than the Peach Me. It's a rather simple drink, requiring only bourbon, peach schnapps, and orange bitters, as per a Difford's Guide recipe. So it's very likely you'll have the ingredients at home, especially if you're a schnapps fan. 

This is a drink that's actually more serious than it looks. At first glance, Peach Me seems like a light peachy drink with soda but it's actually a strong sipping cocktail. No overwhelming, sugary mixers here. This cocktail doesn't rank any higher because it's still pretty bourbon heavy. 

That's, a good thing of course, but the flavor could benefit with some bold peach notes. Muddled peaches could work well in this cocktail, though they might cloud the drink with pulp and fiber. Peach nectar could also suit but might make the drink too sugary. Bourbon and peach are a lovely match. It's just a shame that they aren't more balanced in the Peach Me.

Just one sip of the Brown Derby will transport you away to a swanky 1930s California nightclub. This iconic (and might we add, refreshing) cocktail, which contains bourbon, grapefruit juice, and honey syrup, was created in the early 1930s at the Vendôme Club in Los Angeles (via Dishes Delish). Quite fittingly, it truly screams glamour. The lively citrus notes are underpinned by the more austere bourbon. And the honey sets it all off by adding a subtle sweetness.

The Brown Derby is zingy and bright. The cocktail is simple enough to make at home, though it requires making honey syrup. You could also add maple syrup instead of honey to amp up the warmth of the bourbon. However, the addition of syrup can make this cocktail a little too sweet, as per reviews on Difford's Guide. One reviewer commented that "the flavors fight each other for a while."

What do you make when you have bourbon on hand but not much else? Raid your fridge, grab some jam, and throw together a bourbon jam. It's a brilliant idea, drawing on jam's sticky, sweet ability to temper the rich bourbon a bit.

Cocktail Party suggests using peach and strawberry preserves for intense fruity flavors, but the original recipe calls for blackberry jam. But that's the beauty of this cocktail — it'll work fairly well with just about anything you have on hand. It's made of familiar ingredients that you probably already have at home. The bourbon jam cocktail mixes together bourbon, lemon juice, jam, honey, and sparkling water. There's no need to go out running for special ingredients. 

This cocktail is also noteworthy because it's delicious. It's sweet and easy to sip on. It's even great to make in batches for gatherings. Ultimately, however, it doesn't compare to the more layered, nuanced cocktails that bourbon is known for.

The whiskey smash is one of those classic cocktails that reminds you why it has stood the test of time with each sip. This cocktail was first printed in Jerry Thomas' "The Bartenders Guide" from 1887, according to Liquor.com. 

This drink contains bourbon, lemon wedges, simple syrup, and mint leaves. But the most important part of this drink isn't the ingredients ... it's actually the process of muddling. First, the lemon must be muddled in a shaker. Then, bourbon, syrup, and mint leaves are added and muddled some more. The process of muddling combines each of the ingredients while releasing the oils in the mint and lemons.

The whiskey smash is close to a whiskey sour, with just enough setting it apart to make it memorable. The whiskey smash is easy to concoct, uses simple ingredients that you probably have on hand, and tastes delicious. Based on these facts alone, it's a recipe worth memorizing!

Collins cocktails provide a blank canvas, allowing you to take a few liberties and up your cocktail game. The standard Tom Collins is just gin, lemon juice, simple syrup, and club soda. The John Collins is the bourbon variation and uses bourbon instead of gin. 

While you can jazz it up if you desire, the John Collins is a nod to all the cocktail purists out there. While bitters, herbs, and richly-flavored syrups are fun to play around with, some things are best kept simple. According to Whiskey Advocate, the Tom Collins — initially known as the gin punch  – was invented by London bartender John Collins in the 1830s. Considering its classic nature, this cocktail, with its lovely tart and sweet qualities, probably tastes much like it did back then. 

Though it may be a little too simple, there's something undeniably charming about the pared-down qualities of a John Collins. 

While the original sidecar recipe calls for cognac, the bourbon-based version has become almost as well-loved as the original. As per 2 Food Trippers, the sidecar reached iconic status in 1948, when it was mentioned in David A. Embury's book "The Fine Art of Mixing." While the book included tons of classics, the sidecar was sophisticated enough to pique plenty of interest in the cocktail world. 

A sidecar typically contains cognac, orange liqueur, and fresh lemon juice. Bourbon lovers will appreciate this variation of the classic. Just swap out the cognac with bourbon, and mix. Considering that this is a sophisticated, layered drink, the fact that it comes together in minutes is incredible. 

It's one of those recipes you can memorize and quickly whip up for last-minute guests. The bourbon sidecar will keep you intrigued with its lemony tartness and also take your cocktail game to the next level.

Bourbon and fruit stars don't often star as the leading characters in a cocktail. Is it because the two simply aren't supposed to work together? Well, the blackberry bourbon smash would disagree. This cocktail shows just how magical the combination can be. The berries bring sweet and tart notes that help to lull the bourbon's powerful taste. 

Renee Nicole's Kitchen has a refreshing recipe for a blackberry bourbon smash and describes it as "part mojito and part mint julep, with a citrusy blackberry twist." As with the traditional whiskey smash, this drink is mixed through muddling. It's a blend of bourbon, club soda, lime, frozen blackberries, basil, and sugar. The ingredients are shaken until integrated and then muddled to ensure the berries are broken up.

This drink is refreshing and light. It's a surprising cocktail that reminds you that you might not know bourbon as well as you think you do!

The Kentucky mule contains bourbon and lots of ice that is topped off with ginger beer. It's essentially the same preparation as a Moscow mule, except that the vodka is swapped with bourbon. The end result is a deliciously sweet and well-rounded cocktail that's perfect for sipping on a hot summer night. 

As Bourbon & Banter suggests, you can tailor the Kentucky mule to your personal preferences: "An upside to the Mule is that you do not need to be a certified mixologist to find the parts-per-whole that works for you. Let your taste buds dictate your percentages."

Probably the most important aspect in any version of the mule is the copper mug. The large quantity of crushed ice is important too, as it takes up a significant amount of space and therefore cools more of the drink, while also melting and providing an even dilution. Want to tackle this at home? Get yourself some ice and copper mugs and give it a go!

Imagine creating a world-renowned cocktail out of just four ingredients. Award-winning bartender Sam Ross did it in 2008 (via Liquor.com). Paper Plane is a cocktail that is beloved around the world for its elegance and simplicity. This cocktail brings together bourbon, lemon juice, Aperol, and Amaro Nonino Quintessentia. 

Some recipes demonstrate just how complex a bourbon cocktail can be. Others recipes are surprising and refreshing. But rarely, if ever, do you see that happen in the same glass. That's why the Paper Plane has grabbed cocktail lovers around the world and simply refused to let go. The Robb Report describes this as a cocktail that appeals to both summer and winter drinkers and even those who might not be so keen on whiskey drinks. 

It's universal, which is a tough feat for a bourbon cocktail. This is a drink you will order at the bar, make at home, and tell your friends about. 

For the record, floats can increase a drink's deliciousness tenfold. That's entirely made up, but it's a rule we like to live by. Floats in cocktails can be used to create both flavor and visual appeal (via MasterClass). When the floater is made of red wine, its likeability goes up by another notch. That's exactly how the New York sour earned a spot on this lineup. It contains bourbon, freshly-squeezed lemon juice, sugar syrup, angostura bitters, egg white, and some red wine.

This drink may have been created by a Chicago bartender in the 1880s, who originally named it the continental sour. The New York sour is a more interesting take on a whiskey sour for those who want a little bit more of the wow factor. This drink also gets a few bonus points from wine lovers because the original recipe actually calls for a floater of Claret, which is a British term that is associated with Bordeaux wines. 

Bourbon and cream are surprisingly complementary. It's a shame that the greatness of this combination is not more frequently acknowledged. After all, white Russians and mudslides are traditionally spiked with vodka, and creamy eggnog is made with rum. Bourbon should hardly be left out. That's where the bourbon ball comes in. 

The bourbon ball brings together a rare concoction of bourbon, creme de cocoa liqueur, and heavy cream, so it's worth enjoying every minute of this drink. Bourbon ball also tends to contain hazelnut schnapps, making this drink even more delectable. If you'd like to tone down the richness of this drink, ABC Virginia has a simpler recipe that excludes heavy cream.

As with most milk or cream-based cocktails, this drink needs to be shaken to blend all the components properly. However, once it's shaken and topped with whipped cream, it is a very exciting way to drink bourbon.

A highball is the kind of drink you can make without a recipe. All you have to do is mix your liquor of choice with any carbonated beverage of sorts, and there's your drink. This cocktail doesn't require strict measurements, though Cocktail Contessa suggests a 3:1 or 4:1 ratio for best results. There's nothing elaborate about the concept, but the bourbon highball's beauty lies in its simplicity. 

Since this is such a simply-prepared drink, whiskey quality, ingredient temperature, and preparation steps are of the utmost importance. Since there are just two ingredients, it's essential to make this cocktail the right way for an enjoyable experience. You'd be best off using a high-quality whiskey with just the right ratio of soda water, ginger ale, or any other mixer.

There's something rather intimate and revealing about a highball. It signifies a level of confidence and trust in the inherent flavor profiles of the ingredients, and when made correctly, the sentiment is perfectly justified. 

Maybe it's sneaky to include the Gold Rush on this list when the whiskey sour has already been mentioned. While both cocktails are similar, the Gold Rush uses honey instead of simple syrup, which switches up the taste entirely. The bourbon and lemon juice supply this drink with bright acidity, and the honey works to tone down the sour notes. 

There's still bourbon and lemon juice in the Gold Rush so you have a bright acidity, but the honey takes the abrupt sour notes down just a notch. The drink is similar to a Bee's Knees, in fact, it's essentially the same drink, just with bourbon replacing the gin.

The Gold Rush is actually a fairly new cocktail. The cocktail was created by hospitality worker T.J. Siegal in the mid-2000s and it has been a favorite ever since. The drink is creative but also demonstrates a reverence for past cocktail creations.

According to Bon Appétit, the Boulevardier and the Negroni are cocktail cousins, siblings even. Both are made with Campari and sweet vermouth, though a Negronis typically incorporates gin, while Boulevardiers have bourbon in them. Although less well known than its relative, the Boulevardier has all the distinction.  

This drink can be traced back to a Manhattan bartender Harry McElhone (as per Imbibe Magazine). He relocated during Prohibition so he could continue to sling the cocktails of his dreams. He went to London first, followed by Deauville, France, and then Paris, where he opened his own place called Harry's New York Bar. There, he encountered socialite Erskine Gwynne. The Boulevardier became her trademark drink. The cocktail is named after the magazine that Erskine Gwynne edited, called The Boulevardier. 

The cocktail is made by mixing bourbon, sweet vermouth, and Campari. It has an inviting warmth as opposed to a Negroni's assertive bitterness. It's not a competition, of course, there's a cocktail for everyone, but there's something so appealing and uniquely sophisticated about the Boulevardier.

When you take a swig of the whiskey sour, you expect that first sip to be ... well, sour. But the beauty of this cocktail is its complexity of flavors — it starts off refreshingly tart, then pleases with notes of sweetness and warmth. These varied hints of flavor are exactly what elevate this drink from a simple cocktail to a feast for the taste buds. It might not be the most serious cocktail in this lineup but it suits a lot of different occasions and seasons. 

Bon Appétit recipe calls for bourbon, fresh lemon juice, simple syrup as well as an orange wedge and cherry for garnish. It's simple enough to make at home though it's important to get the proportions right. Make sure you use freshly squeezed lemon juice, not the bottled stuff. You can even swap out the lemon juice for lime if you're short on ingredients. It's the fresh acidic notes that are the most important.

The mint julep may seem like a surprising choice. Any unsuspecting drinker might not see the link between bourbon and summer, but the mint julep doesn't care about your expectations. This Southern cocktail is a combination of bourbon, simple syrup, and mint all muddled together. Also, it's essential to use crushed ice in a mint julep. The crushed ice melts and helps transform this drink from a heavy, bourbon cocktail to a beautifully integrated refreshment in liquid form. Mint juleps are traditionally served in pewter cups. 

Racegoers have been enjoying the cocktail there for nearly a century. Mint juleps are the signature drink of the Kentucky Derby. Nearly 120,000 mint juleps are consumed every year at the Kentucky Oaks and Kentucky Derby weekend (via The Kentucky Derby). The mint julep is a party drink and it's thirst-quenching while also packing a punch. This summertime sipper is truly uplifting and delicious.

What a life the Manhattan cocktail has led. The drink has been popular since the 19th century. It survived the prohibition era in the United States and even gained traction overseas (via Liquor.com). Today, the Manhattan is a beautifully classic cocktail. It's a reminder that less is indeed more. Whether you live by those words or not, you'll probably love the Manhattan. 

It contains whiskey, sweet vermouth, and bitters. It's important to match your whiskey to your vermouth to make sure that they don't overwhelm each other and the overall taste remains balanced. Angostura bitters are typically used, although historically, some recipes have also suggested using Peruvian bitters. This cocktail is a classic at most bars. As per Simple Joy, it's traditionally served in classy coupe glasses, giving the cocktail a hint of sophistication. More importantly, it has a stellar host of flavors, with layers of subtle sweetness, aromatic, herbal notes, and some hints of bitterness. 

A hot toddy seems like a controversial second choice. There are so many delicious bourbon cocktails to choose from, and yet, very few of them are served piping hot in a stemmed mug. Its uniqueness is exactly what makes the hot toddy so appealing. It's in a league of its own. What else can you drink as a warm, comforting beverage before bed or as a pick-me-up on a cold winter day?

According to the Sip Awards, the hot toddy originates from "taddy," which is a fermented palm sap drink that was consumed in India in the 1610s. In 1768, the cocktail evolved into the drink we know it as today, and alcohol was added to a blend of hot water, spices, and sugar. 

The hot toddy is a classic drink and it's also highly customizable — the only rules are that you include hot water, bourbon, honey, and lemon juice. Other ways to jazz up the drink include using maple syrup instead of honey and including a cinnamon stick or star anise for some spice. 

If you're a bourbon fan, then this one should come as no surprise. The Old Fashioned is classic, yet that first sip always feels daring and new. The Old Fashioned has a fitting name. It is one of the oldest known cocktails, with roots that trace back to 1880, as per Vinepair. 

The drink is the creation of the distiller James E. Pepper, who served it to businessmen and at the Waldorf Astoria Hotel in New York. The spot was frequented by the likes of Fred Pabst and John D. Rockefeller. With just bourbon, bitters, and simple syrup, it's a deceptively easy cocktail to make, though some details are non-negotiable in the making of this cocktail. 

The ice cube must be large enough so that it melts slowly, so as not to quickly dilute the drink. The citrus twist is essential as it lends a nice aroma to the drink. It's the drink to have when you want to celebrate a momentous event, catch up with friends, or wind down after dinner. Over the years, this cocktail has become a completely irreplaceable and respected addition to the drinks world. May it always stay that way.