‘Mad Men’ Sets Kentucky Derby Mood

Pop Culture

“Mad Men” cast on the Derby party set. (Photos courtesy AMC TV)

On May 17 at approximately 10:01 CST, I will join the nation-wide dirge of “Mad Men” "maddicts" mourning the end of the era as the credits of the series finale roll.

As the fanfare for the finale swells, I remember one episode that has special import: Season three, episode three, titled “My Old Kentucky Home,” in which Roger Sterling hosts a Kentucky Derby party.

Roger’s invitations precipitate a pre-party ripple. They cause dissention among Sterling Cooper’s creative department: some of the team is included, others are not (and get stuck working on the weekend). Harry stresses about what to wear. “Are any of you wearing seersucker? Because I don’t want to look like I’m in a barbershop quartet,” he says. A very pregnant Betty buys a new dress and nylons for the event (which evokes one of Don’s most famous lines, uttered during the series pilot, “What you call love was invented by guys like me to sell nylons”).

As Don and Betty prepare to depart for Derby day, Sally reads a book with Grandpa Gene that is more commentary on her parents than history: “Fashion was the only law, pleasure was the only pursuit and the splendor of dress and furniture was the only distinction of the citizens of Antioch.”

Derby day Mad Men style is a microcosm of what devotees love about the show: the retro glamor, the three-martini lunch, the political incorrectness, hating Peter, the brokenness of the human condition.

The party is held in an opulent tent on the grounds of an exclusive country club. The color scheme is green and white. The elaborate set-up includes tablecloths, a horse head ice sculpture, hanging lanterns, tied-back curtains and an abundance of red roses. My two favorite touches are the dance floor with a horse and jockey in the middle surrounded by the words “Derby Day 1963” and a Churchill Downs tote board featuring the same logo. A jazz band plays while women in gorgeous hats hold cocktails.


The camera doesn’t linger on all of the luxury. I’ve read creator Matthew Weiner believes the devil is in the details: everything, up to the last scrap of paper on a desk, must be period and authentic. Even though Roger’s purpose seems to be to showcase his complete happiness with his secretary-turned-wife in their shocking whirlwind marriage, who wouldn’t want to attend his party?

Don Draper—ever elusively cool—is the one person who is reluctant to be there. “I’m at work disguised as a party,” he says into his glass. But even Don must admit Roger’s party changes his life: he meets Conrad Hilton, and Betty, who is mongo pregnant and says she feels like an open umbrella, meets Henry Francis, whom she will marry sooner rather than later (all hail the power of Betty, who can attract a new man while majorly expecting). In clever foreshadowing, the conversation veers to where Henry has been: Governor Rockefeller has just married Happy, who has been divorced for one month and who has four children because they’re in love.

The attendees jockey for position. Trudy postures, saying she grew up in a club just like this and worries “with this set one of my old beaus might appear.” Harry and Jennifer Crain try to mingle and fail miserably. “Well, we’re really having a good time,” he says awkwardly.

The episode is not without major cringes. Chief among them is Roger serenading his ridiculously young wife in blackface while she pretends he is hilarious (butchering “My Old Kentucky Home” almost irreparably). A close second cringe is Peter and Trudy doing the Charleston. The new Mrs. Sterling gets drunk, which causes a charged exchange between Roger and Don.

“It’s a mistake to be conspicuously happy. Some people don’t like it,” Roger says. Don replies, “No one thinks you’re happy. They think you’re foolish.”

Even though I side with Don on this one, Roger provides a nice summation of the Derby day experience: “That’s the great thing about a place like this. You get to come here and be happy, and you get to choose your guests,” he says, and walks away.

Season three, episode three (available on Netflix) of “Mad Men” will help any race fan get in the mood for the Kentucky Derby while highlighting the brilliance of a show ending frighteningly soon.

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