The Old Fashioned in Pop Culture: From Don Draper to Today

The Old Fashioned in pop culture has a strange dual life. For most of the 20th century, the cocktail was either invisible (overshadowed by the Martini and Manhattan) or actively unfashionable (eclipsed in the 1980s by neon-blue daiquiri culture). Then in 2007, AMC's Mad Men premiered, Don Draper ordered an Old Fashioned in episode 1, and the cocktail's modern revival officially started. The years since have produced a steady stream of Old Fashioneds in films, TV, music, and literature — turning the cocktail back into a cultural shorthand for "I am a serious adult drinker who knows what I'm ordering."

This is a tour of the Old Fashioned's pop-culture history, from its mid-century quietude through the Mad Men resurgence to its current ubiquity. For the full cocktail history, see The History of the Old Fashioned.

Pre-Mad Men: The Quiet Years (1950s–2000s)

From the post-Prohibition era through the 1970s, the Old Fashioned was drunk steadily but not glamorously. Sinatra was photographed with one occasionally; so were various politicians and steakhouse regulars. But the Old Fashioned wasn't the cocktail of the moment — that title belonged first to the Martini (1950s sophisticate cocktail), then the Manhattan (1960s power drink), then to a slew of tropical cocktails (1970s). The Old Fashioned was an "Uncle's drink" — what someone over 50 ordered at a Holiday Inn bar.

The 1980s and 1990s were particularly bad for the cocktail. Wisconsin had developed its sweet, fruit-muddled regional version (see Brandy Old Fashioned), but the cocktail was fundamentally seen as old-fashioned in the literal sense: dated, unfashionable, boring. The Cosmopolitan, the Appletini, and the Sex on the Beach defined cocktail culture.

2007–2015: The Mad Men Resurgence

AMC's Mad Men premiered July 19, 2007. In the pilot, advertising executive Don Draper orders an Old Fashioned. Throughout the series' seven seasons, the cocktail reappears constantly — in office scenes, restaurant scenes, hotel-bar scenes. Don Draper doesn't drink Old Fashioneds because of historical accuracy (1960s ad executives drank a wider variety of drinks); he drinks them because the show's creators chose the Old Fashioned as the cocktail that visually communicated "this man is a serious adult."

The cultural impact was immediate. Cocktail bar bartenders reported a surge in Old Fashioned orders within weeks of each Mad Men season premiere. Bourbon and rye sales increased measurably during the show's run. The cocktail moved from "Uncle's drink" to "Don Draper's drink" — an entirely different cultural valence.

Mad Men's Specific Old Fashioned

The cocktail Don Draper drinks on Mad Men is technically the 1960s steakhouse version: rye whiskey, sugar, Angostura, with a muddled orange slice and brandied cherry. This is closer to the Wisconsin tradition than the modern craft-cocktail interpretation. Period-correct, visually distinctive, but not what most modern Old Fashioned drinkers actually want.

The show's bartender consultant, Mike Flynn, has discussed the recipe choice — they wanted the cocktail to look properly mid-century, with the muddled fruit being a visible cue. The modern craft-cocktail Old Fashioned (no muddled fruit, demerara syrup, expressed orange peel) wouldn't have read as period-correct on screen.

Other Pop Culture Appearances

Title	Year	Notes
Mad Men (TV)	2007–2015	The defining modern OF reference; Don Draper
Crazy Stupid Love (film)	2011	Ryan Gosling's character orders OFs throughout
House of Cards (TV)	2013–2018	Frank Underwood's drink at home
Justified (TV)	2010–2015	Raylan Givens drinks bourbon Old Fashioneds
Yellowstone (TV)	2018–present	John Dutton's standard drink
Billions (TV)	2016–present	Bobby Axelrod drinks them in negotiations
The Big Lebowski (film)	1998	White Russian, not OF — but listed for the cultural cocktail-as-character technique

The pattern: when a screenwriter wants to communicate "this character is serious, traditional, sophisticated, old-money or aspiring-old-money," the Old Fashioned is the cocktail of choice. The Martini communicates "elegant," the Manhattan communicates "powerful," the Old Fashioned communicates "substantial."

Music and Literature

• Frank Sinatra reportedly favored the Old Fashioned, particularly with Jack Daniel's. His personal recipe is documented and widely cited.
• Hemingway mentions Old Fashioneds in passing in several short stories, though he was more famous for Mojitos and Daiquiris.
• Country music mentions Old Fashioneds frequently — most famously in Cody Johnson's Old Fashioned Country Boys and various other contemporary country songs.
• Tom Wolfe's Bonfire of the Vanities features Old Fashioned ordering as character signaling.
• The Crown (Netflix) has Prince Philip drinking Old Fashioneds in scenes set in the 1960s and 1970s.

The Cocktail-as-Character Technique

Screenwriters and novelists use cocktail orders as character shorthand. The Old Fashioned communicates a specific set of values:

• Tradition over trend. The character knows the classics; doesn't care about the cocktail of the month.
• Substance over flash. Spirit-forward, not sweet/colorful/garnish-heavy.
• Patience. The Old Fashioned is built for slow drinking; the character has time.
• Confidence. Ordering an Old Fashioned signals "I know what I want" — vs. browsing a cocktail menu.
• Mid-century or older sensibility. The cocktail's heritage is part of its meaning.

This is why almost every fictional powerful businessman drinks Old Fashioneds. The cocktail does narrative work without needing dialogue.

The Anti-Old-Fashioned in Pop Culture

If the Old Fashioned signals "substantial adult," the cocktail equivalent of trying-too-hard tends to be elaborate craft cocktails with multiple house-made ingredients. The 2010s craft-cocktail-bar wave produced a parallel pop-culture trope: the character who orders something with "house-infused mezcal, hibiscus shrub, and torched cardamom." This character is being mocked. The Old Fashioned drinker is being respected.

The cultural distinction matters: simple, classical, traditional > elaborate, novel, fashionable.

The Modern Era: Post-Mad Men

Mad Men ended in 2015, but its cocktail effect persists. The Old Fashioned has settled into a stable position as one of the top-three most-ordered classic cocktails in America (alongside Manhattan and Margarita). It's no longer trending up — it's the default. New craft cocktail bars all carry an Old Fashioned on the menu; failing to do so is now a signal of inexperience.

What's changed since 2015:

• Craft-cocktail interpretation has standardized. The "modern" Old Fashioned (rye, demerara syrup, expressed orange peel, large rock, no muddled fruit) is now the default at quality bars.
• Premium rye sales tracked the cocktail's popularity. Rye whiskey production capacity tripled between 2007 and 2025.
• Old Fashioned variations proliferated. Smoked, maple, cherry, espresso, fig — the variation library grew dramatically.
• Wisconsin and modern OFs split into separate cocktails. The Wisconsin-style brandy Old Fashioned with muddled fruit is now distinct from the modern craft-cocktail Old Fashioned.

Frequently Asked Questions

What does Don Draper drink on Mad Men?

Old Fashioneds, primarily — though he drinks Canadian Club neat in some scenes and various other drinks throughout the series. The Old Fashioned is his most-associated cocktail and the one he orders in the pilot episode. The Mad Men version uses muddled orange slice and brandied cherry, period-correct for the 1960s.

Did Mad Men make the Old Fashioned popular?

Mad Men was the major cultural catalyst for the modern Old Fashioned resurgence. Cocktail bartenders reported immediate increases in Old Fashioned orders following the show's premiere in 2007 and after each season. Combined with the broader craft-cocktail revival, Mad Men shifted the Old Fashioned from "Uncle's drink" to "serious adult drink."

Is the Old Fashioned in The Crown accurate to the period?

Yes — Prince Philip and other royals would have had access to and likely drunk Old Fashioneds during the 1960s–1970s scenes depicted. Royal drinking culture historically included American whiskey cocktails alongside British spirits.

What pop culture made the Old Fashioned famous?

Mad Men (2007–2015) was the primary cultural catalyst. Subsequent shows (Justified, House of Cards, Yellowstone, Billions) reinforced the cocktail's "serious-adult" cultural meaning. Pre-Mad Men, the Old Fashioned was unfashionable; post-Mad Men, it's a classic.

Why do TV characters drink Old Fashioneds?

The cocktail signals tradition, substance, confidence, and mid-century sensibility. Screenwriters use it as character shorthand for "this person is a serious adult who knows what they want." Compare to the Martini (elegant), Manhattan (powerful), or Cosmopolitan (modern) — each cocktail does specific narrative work.

What was the Old Fashioned's pop-culture status before Mad Men?

Largely invisible. The 1980s and 1990s favored sweet/colorful cocktails (Cosmopolitans, Appletinis). The Old Fashioned was seen as an "uncle's drink" — what someone over 50 ordered at a Holiday Inn bar. Mad Men flipped that perception in 2007.

More Archive: Full History · Who Invented It · What Is an Old Fashioned

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