Sterling Cooper copywriter Paul Kinsey is at his insufferable best when he hosts a party at his Montclair, New Jersey, bachelor pad (season 2, episode 2; “Flight 1”). His neighbors mingle with the younger set from Sterling Cooper, all of them drinking whiskey sours out of glass jars. Paul, clad in an ascot and holding a pipe, strolls around holding a brandy snifter with rum he claims was salvaged from an 1871 shipwreck.
When Pete Campbell asks him why he didn’t get an apartment in the Village, Paul tries to paint Montclair as the leading edge of hip. At one point Paul introduces his new girlfriend, an African American woman named Sheila Winter, to Joan Holloway. Later in the episode Joan, with whom Paul has a past, delivers a devastating takedown of Paul and his Bohemian pretensions—including his shipwrecked rum and his attraction to Sheila—but the humble whiskey sour is surely not part of his posturing.
A traditional whiskey sour is a simple mix of whiskey (usually bourbon), lemon juice, and sugar, garnished with an orange slice and a cherry. Many drinkers today know the whiskey sour as a drink made with a commercial premade sour “mix,” but a traditional whiskey sour, such as the one that appeared in the 1862 edition of Jerry Thomas’ Bar-Tenders Guide or How to Mix Drinks, would never be made with a commercial mix. Still, the traditional whiskey sour was an unpretentious affair.
The whiskey sour appears again two seasons later, when Lane Pryce’s cruel, domineering father, Raymond, comes to town and Lane implores Don Draper to join them for dinner. Lane takes them to the Playboy Club, where Lane’s African American girlfriend, Toni Charles, works as a Playboy Bunny. Judy, one of the Bunnies, comes to take their order and Lane asks for three whiskey sours, but the disagreeable Raymond wants iced bourbon instead. So, make it two whiskey sours.
Hugh Hefner’s aging Playboy empire is still alive but, while Playboy is widely seen as an anachronism today, in the 1960s it embodied a cool, modern sophistication. In addition to his “lifestyle” magazine and syndicated television shows—Playboy’s Penthouse (1959–60) and Playboy After Dark (1969–70), which were set as parties featuring Playboy Playmates and celebrities at Hefner’s penthouse—Hefner owned the famous Playboy Clubs, nightclubs featuring scantily clad Playboy Bunnies as servers. The first Playboy Club opened in Chicago in 1960, and others soon followed in the United States and elsewhere. The New York club opened in December 1963 on East 59th Street in Manhattan, and so was relatively new when Lane, his father, and Don visited. For men like Lane Pryce, membership in the Playboy Club was a status symbol. Members were called “keyholders,” because membership was the key that opened the door to the pleasures of the Playboy lifestyle.
The whiskey sour Lane and Don would have imbibed at the Playboy Club may well be found in Playboy’s Host & Bar Book by Thomas Mario (1971). Lane should have followed the advice in Mario’s book: “Every prearranged drinking session calls for two kinds of alchemy: The first is mixing potables; the second is mixing people.” We doubt Raymond Pryce mixed well with anyone; he’s about as sour as they come.
ACTOR HUGH O’BRIEN WITH JOY PERCIVAL, “BUNNY JILL,” AT A PLAYBOY CLUB IN THE 1960S
FROM PLAYBOY’S HOST & BAR BOOK BY THOMAS MARIO (PLAYBOY, 1971)
NOTE: For a more tart drink, reduce the amount of sugar. For a mellower drink, substitute ½ ounce lemon juice and ¼ ounce of orange juice for ¾ ounce of lemon juice.
2 ounces blended whiskey
3⁄4 ounce lemon juice
1 teaspoon sugar
1⁄2 slice lemon
1 maraschino cherry (optional)
YIELD: 1 DRINK