The Classics
The most famous bourbon cocktails are certainly the Old Fashioned and the Manhattan. The Old Fashioned was first mixed at Louisville's Pendennis Club in the 1880s for a member, a retired Civil War officer, who didn't like the taste of bourbon. He did, however, want to stay on the good side of the distillery owners who were his fellow members. So the bartender came up with the eminently palatable Old Fashioned. (This has also been my philosophy in concocting bourbon cocktails—to allow people to enjoy bourbon who thought they didn't like it!) Eventually, like the Martini, the Old Fashioned even spawned its own eponymous glass. The squat bar glass came to be called an Old Fashioned glass.
The Manhattan also has a colorful tale attached to it. The popular version is that it was created in 1874 at New York City's Manhattan Club at an event hosted by Lady Jennie Churchill, American wife of British parliamentarian Lord Randolph Churchill, the parents of future Prime Minister Winston Churchill. The soiree was held in honor of New York's newly elected governor, Samuel J. Tilden. Or not. There are also some indications that a Manhattan-like cocktail was being served several years before this.
In addition to the Old Fashioned and the Manhattan, we've included my takes on other bourbon drinks that have attained the status of classics—the Hot Toddy, John Collins, Mint Julep, Sazerac, and Whiskey Sour.
OLD FASHIONED 
1 tablespoon simple syrup
6 dashes Angostura bitters
1 orange wedge
1 red cherry
2 ounces water
2 ounces Kentucky bourbon
Put the simple syrup and bitters in the glass. Add orange wedge and cherry; muddle. Add ice, water, and bourbon, and stir. Garnish with a long-stem cherry.
For each version of the Manhattan, combine bourbon, vermouth, and bitters over ice and shake. Strain into a chilled glass. Nothing ruins a Manhattan faster than old or cheap vermouth. Use Noilly Prat vermouths from France and buy the small bottles. Yes, the traditional Manhattan has bitters in it.
The Classics. Whiskey Sour (left), John Collins (right), Old Fashioned (foreground), and Manhattan (background).
2 ounces Kentucky bourbon
¼ounce Noilly Prat sweet vermouth
4 dashes Angostura bitters
Garnish with a red cherry.
2 ounces Kentucky bourbon
¼ ounce Noilly Prat dry vermouth
See note under Original Manhattan, previous page. Garnish with a large green pitted olive.
PERFECT MANHATTAN 
2 ounces Kentucky bourbon
¼ ounce Noilly Prat dry vermouth
¼ ounce Noilly Prat sweet vermouth
3–4 dashes Angostura bitters
See note under Original Manhattan, previous page. Garnish with a large lemon twist.
HOT TODDY MUG 
This is the favorite way to take the chill off during a damp, chilly Kentucky winter. An armchair beside a blazing fireplace is a pleasant optional ingredient.
5 ounces hot water just off the boil
2 ounces Kentucky bourbon
1 tablespoon simple syrup
lemon twist
Pour hot water into an 8–9 ounce stoneware mug. Add bourbon, syrup, and a lemon twist.
JOHN COLLINS 
This variation on the gin-based Tom Collins takes its name from “John Barleycorn,” a traditional nickname for bourbon.
2 ounces Kentucky bourbon
½ ounce simple syrup
1 ounce sweet and sour mix
2 ounces club soda
To a glass filled with ice, add bourbon, syrup, and sweet and sour mix; shake. Add club soda. Squeeze and drop a large lemon wedge into the glass. Add a long straw and a cherry.
A sterling silver julep cup is the ultimate vessel in which to serve this classic. The next best is one of the official souvenir glasses made each year for the Kentucky Derby. These glasses are readily available in liquor stores in the Louisville area starting in March and are sold until the year's supply runs out. My collection of Derby glasses dates back to 1969, the year my daughter was born.
1 ounce simple syrup
5–7 mint leaves (Kentucky Colonel variety if available)
3 ounces Kentucky bourbon
3 ounces water
Into a large mixing glass pour simple syrup, add mint, and muddle well. Add bourbon and water. Fill with crushed ice or small ice cubes, and shake. Garnish with a large sprig of fresh mint and add a long straw.
SAZERAC
This potent classic takes its name from the Sazerac Coffee House in New Orleans, where it was first served.
1 teaspoon Pernod
2 ounces Kentucky bourbon
1 tablespoon simple syrup
6 dashes Peychaud's bitters
Pour Pernod into the glass and swirl to coat. Pour out the excess. Add ice, bourbon, syrup, and bitters; shake. Garnish with a large lemon twist.
WHISKEY SOUR
Sometime in the mid-nineteenth century, bartenders started doctoring bourbon and rye with lemon juice, and “sour” drinks were born. The citrus employed here is orange.
2 ounces Kentucky bourbon
1 tablespoon simple syrup
1 ounce sweet and sour mix
½ ounce fresh orange juice
In a glass filled with ice, combine all ingredients; shake. Garnish with an orange wheel and a cherry.