TV
The Old Fashioned, Dry Martini, Alexander and Whiskey Sour: the scenes, who drinks what, and what’s said.
Season 1, Episode 1, “Smoke Gets in Your Eyes” (2007) · Don Draper
In the series' opening scene, Don sits in a Manhattan bar working out a Lucky Strike pitch on a cocktail napkin and orders another Old Fashioned.
Sources: The Press Democrat - Best cocktails for 'Mad Men' finale; BAMF Style - Mad Men 'Smoke Gets In Your Eyes'; Wikipedia - Old fashioned (cocktail)
Season 1, Episode 7, “Red in the Face” (2007) · Roger Sterling and Don Draper
After Roger hits on Betty, Don gets back at him with a long lunch of martinis and raw oysters, then bribes the elevator man so they have to climb 23 floors, and Roger throws up in front of clients.
Sources: Bustle (Food52) - The 10 Best 'Mad Men' Food And Drink Moments; The A.V. Club - Mad Men: Red in the Face; Paste - 25 TV Characters Who Love to Drink
Season 1, Episode 11, “Indian Summer” (2007) · Peggy Olson
Peggy drinks a Brandy Alexander on a date and remarks that Joan often orders the drink for her.
Sources: Wikipedia - Brandy Alexander (In film and television); Miss Charming (Cheryl Charming) - Cocktails in Television
Season 3, Episode 3, “My Old Kentucky Home” (2009) · Don Draper (with Conrad 'Connie' Hilton)
Leaving Roger's Derby party, Don finds an unattended country-club bar, goes behind it and makes Old Fashioneds for himself and a stranger named Connie, who later turns out to be Conrad Hilton.
Sources: Wikipedia - My Old Kentucky Home (Mad Men); Tasting Table - 15 Most Iconic Cocktails From Film And Television; Mashed - From Scotch To Soda: The Go-To Drinks Of 15 TV Icons
Season 4, Episode 10, “Hands and Knees” (2010) · Lane Pryce
On a night out with Don and his visiting father at the Playboy Club, Lane settles on whiskey sours.
“Three whiskey sours ought to do.”
See the full quote on TV Quotes →
Sources: Wikiquote - Mad Men (season 4), 'Hands and Knees'; Miss Charming (Cheryl Charming) - Cocktails in Television