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Drink like Don: Try these 'Mad Men'-inspired cocktails

Take a sip from Don Draper's cup by making yourself a classic old fashioned.

The long-awaited season five premiere of “Mad Men” finally airs on Sunday, March 25, and there’s no better way to celebrate than imbibing on some “Mad Men”- inspired cocktails (we’re even imagining that sexy Don Draper is serving ‘em up to us). 

Some of these tipples come from top bartenders who reimagine 1960s-style cocktails -- a world ripe with tiki drinks, martinis and the Old Fashioned. We also turned to “The Unofficial Mad Men Cookbook” by Judy Gelman and Peter Zheutlin, which highlights recipes based on dishes and drinks seen in the show. 


We have to start with Don Draper’s iconic Old Fashioned, which is shown in the first episode and through the series. In the show’s opening scene, Don jots notes on a cocktail napkin about Sterling Cooper’s top client, Lucky Strike cigarettes. The waiter comes by and, in that dapper Don Draper way, he orders another Old Fashioned. 

Don’s Old Fashioned
Recipe courtesy of The Grand Central Oyster Bar, New York, New York, via “The Unofficial Mad Men Cookbook”

  • 1 orange slice
  • 1 maraschino cherry
  • 1 teaspoon sugar
  • Few drops of Angostura bitters
  • A splash of soda water to muddle ingredients
  • 2 ½ ounces rye or bourbon

Note: Bourbon or rye may be used in the Old Fashioned. Rye was originally used, and The Grand Central Oyster Bar is starting to use rye again in these drinks; they use Michters’, but Don would likely choose Canadian Club, the brand we often see in his office and home. Seagrams V.O. and Crown Royal were also popular in the 1960s, says Jonathan Rogers of The Grand Central Oyster Bar. 

In a mixing glass muddle orange slice, cherry, sugar, bitters and a little soda water, breaking up cherry and orange until flavor is released. Add soda water so cherry is wet and sugar is melted. Add bourbon or rye and serve over rocks, if desired 

In addition to this classic Old Fashioned, Hill Country Barbecue’s Washington D.C. location does a riff called the Dick Whitman (Don’s real name in the show). 

The Dick Whitman
Serve in a highball glass. Saturate 1 sugar cube with 4 dashes of Angostura bitters until dissolved. Add 2 ounces Whistlepig Rye. Fill glass with ice and stir. For garnish, add one flamed orange peel and one maraschino cherry 

Bartenders at hotel-bar-museum 21C in Louisville, Ky., whip up a drink in reverence of Joan Holloway, the buxom redheaded more-than-your-average secretary and apple of Roger Sterling’s eye. This cocktail is light, bubbly and features a splash a red -- just like Joan.

The Holloway 
Mix 1 ounce Drambuie and a dash peach bitters. Fill with Champagne. Drop in a strawberry slice and serve in a flute glass.


After Roger Sterling divorces his wife and marries the 22-year-old Jane, he changes habits to reflect a more youthful vibe. That’s why we see him forgoing his usual martini, and instead imbibing in Pfaff’s Subway Rumbles cocktail while dining with his young bride.

Subway Rumbles
Courtesy of Pfaff’s

  • 1 ounce The Black Grouse (or other blended Scotch)
  • 1 ounce Bols Genever 
  • ¾ ounce lemon juice 
  • ¾ ounce grenadine  
  • 1 fresh egg white 

Add all ingredients to iced shaker, shake, and then strain into martini glass. Add 1 dash Peychaud’s bitters. Serve in a martini glass.
Garnish with orange twist. 

 As the reluctant housewife, Betty Draper would probably be found sipping on a light, gin based drink like the Cucumber Collins. In honor of the "Mad Men" premier, Sullivan’s Steakhouse created this drink. 

Cucumber Collins
Serve in a tall glass

  • 2 ounces Hendricks Gin
  • 1 ounce fresh lemon juice
  • 1 ounce simple syrup
  • 4 thin cucumber slices muddled
  • 1 ounce club soda 


In mixing glass, muddle cucumber with simple syrup. Add gin and juice then fill glass with ice and shake in shaker tin. Strain and pour over ice into glass. Top with club soda. Garnish with a cucumber slice.

La Fonda del Sol

Normally you wouldn’t think of Spanish-style drinks making their way into an account executive’s hand, but the 50-year-old revival restaurant La Fonda del Sol in New York serves cocktails that pay homage to the 1960s. One tipple, the anejo highball, invokes an adventure Don Draper may have taken while hanging with the hippie crowd in California.

Anejo Highball
Serve in a highball glass

  • 1 ½ ounce Anejo rum
  • ½ ounce orange curacao
  • ½ ounce lime juice
  • 2 dashes Angostura bitters
  • 2 ounces ginger beer
  • lime and orange slice for garnish

Fill glass with ice and add, in order, rum, curacao, lime juice, and bitters. Top with ginger beer and garnish.

As introduced in season one, the Mai Thai debuted when heiress Rachel Menken and Don Draper dined at the El Morocco on 54thStreet. While Don gets his usual Old Fashioned, Rachel goes for the tall, brightly garnished tiki drink, complete with umbrella.

Mai Thai
Adapted from Trader Vic ’s Rum Cookery and Drinkery by Victor J. Bergeron (Doubleday, 1974) via "The Unofficial Mad Men Cookbook"

  • 1 lime
  • 1 ounce Jamaican rum
  • 1 ounce Martinique rum
  • 2 ounces orange juice (optional)
  • ½ ounce orange curaçao 
  • ¼ ounce orgeat syrup 
  • ¼ ounce rock candy syrup (simple syrup)
  • Sprig of mint, for garnish
  • Fruit stick, for garnish (pineapple, mango, grapes, apple, etc.)

Squeeze lime over shaved ice in a cocktail shaker. Save ½ of the lime shell for garnish. Add all liquids and hand-shake. Pour over shaved ice and decorate with mint, fruit stick, and lime peel

What about the other, younger executives who, when not downing glasses of Scotch in their offices, like to have a night on the town? We can easily see Pete Campbell, Harry Crane and Paul Kingsley pontificating about life with Raines Law Room’s cocktail maven Meaghan Dorman and her crafty variation of a Bobby Burns, the Roman Poet.

Roman Poet
Courtesy of Meaghan Dorman 

2 ounce Great King Street Scotch whisky
¾ ounce Amaro Ramazzoti
¼ ounce Benedictine
2 dashes Peychaud bitters




Stir with ice then strain into a cocktail glass. Garnish with a grapefruit twist.