Roger Sterling as a Hemingway Character

Apart from his heavy drinking, Roger Sterling appears to have little in common with the outdoorsmen and adventurers often featured in Hemingway novels. Sterling’s coddled upbringing and prominent position atop an advertising agency starkly contrast the rough and dangerous existence of Robert Jordan in For Whom the Bell Tolls. During a recent rewatch of the Mad Men series, a stray comment made by a minor character, however, revealed a connection between Hemingway’s world and the urban glitz of Madison Avenue in the 1960’s.

In “The Gypsy and the Hobo,” (Season 3, Episode 11) Roger Sterling reconnects with an old girlfriend, Annabelle Mathis. Visiting New York for business purposes, Mathis asks Sterling Cooper to help ameliorate her dog food company’s public relation issues. After a professional meeting in the office, Sterling and Mathis extend the reunion to an offsite location and meet for dinner later that evening. The former paramours reminisce about their time together in Paris, and Mathis states that Sterling strutted around the city “hoping to be a character in someone else’s novel.”

Admittedly, the first few times I viewed the episode, I did not think much of this digression. For those unfamiliar with Mad Men, Roger Sterling is a libertine advertising executive who inherited his position from his father. He often persuades Don Draper (the protagonist of Mad Men) to join him for evenings of excessive consumption and trips to underground casinos. When Annabelle Mathis mentions Sterling’s activities in Paris, her description fits his overall character profile and most viewers (including me) most likely miss the allusion to Hemingway. Vigilant devotees of both Mad Men and Hemingway will draw the connection, however, when they combine Mathis’s statements about Roger’s boxing and acting like a “character in someone else’s novel.”

Possibly my favorite work of fiction, The Sun Also Rises is a quintessential Hemingway novel. The story follows Jake Barnes on a booze fueled tour of Paris, Bayonne, and Pamplona, and in typical Hemingway fashion, the tale is replete with love triangles and gory bull fights.

Hemingway and the Pamplona Retinue

One character in the novel, Robert Cohn, is remarkably similar to the younger Roger Sterling that Mathis describes over dinner. Cohn, an American, is relatively wealthier than the other travelers, an Ivy league graduate, and a trained boxer. At one point in the story, he even pummels a matador during a fit of jealously. Cohn is actually based on Hemingway’s friend, Harold Loeb, and the entire book is inspired by the several trips that Hemingway took to Pamplona.

Maybe you can compare Cohn to many well bred American amateur boxers during this period, but it’s undeniably fun to imagine Sterling strutting around 1920s Paris and possibly knocking a matador to the floor.