Perhaps the most cocktail-centric moment in the entire history of the AMC series "Mad Men" comes in "My Old Kentucky Home," the third episode of the third season. That lead character Don Draper likes Old Fashioneds, we know. In a central scene in this episode, we actually get to see him make one.
Trapped at a country club event thrown by his boss, Roger Sterling (mint juleps are served—it's a Kentucky Derby theme), Draper escapes to the club's bar room in search of liquid relief more to his liking. There he hops behind the bar and has at the bottles and equipment like a pro. Or, at least, like a man who knows what he wants.
First he grabs two rocks glasses and plops a good-sized sugar cube in each. He then takes out the Old Overholt—the first time this rye brand has been featured on the show. He soaks the cubes with a good amount of bitters (Angostura, I assume, though the bottle he used was unmarked and didn't have Angostura's distinctive oversized label). That done, he takes a large mixing glass, fills it with ice to chill. Draper pours in about four ounces of rye and tops that with soda water. He then muddles away at the two glasses, which now contain a cherry. (He is not seen putting those in.) He gives the bar glass mixture a quick stir with a bar spoon, and then pours the contents, ice and all, in even amounts into the rocks glasses, and drops an orange slice on top of each drink. When he hands one of the cocktails to his only companion in the room, a southerner named Connie (who may or may not be Conrad Hilton).
Not the most graceful way to make an Old Fashioned. All that unneeded soda, no jiggering, too much bitters and the sloppy transfer of the whisky and ice into the glasses. But probably an accurate example for the time, considering it's a depiction of a regular 1960s guy making himself a drink in the way he's become accustomed to it. Anyway, Connie called it "a hell of a cocktail."
Otherwise, the episode saw various members of "creative" at Sterling Cooper trying to hatch ideas for a Bacardi campaign called "Bacardi Beach."
In episode five, "The Fog," Don, while waiting for Betty to give birth to their third child, shares a bottle of Johnnie Walker Red Label with an expectant father prison guard in the "solarium" at the hospital. The Walker label and bottle hasn't changed much over the years. Later, Peggy Olson has a Bloody Mary at lunch with Herman "Duck" Philips, a Draper antagonist from season two who makes a reappearance.
