TV Slop: Mad Men

Don Draper’s Earthly Odyssey Through the 9 Circles of Hell

Senote Keriakes · September 5, 2023

7 min read

The various circles of hell in Dante’s Inferno are inhabited by people who have committed sins of varying degrees (and degrees) of intensity. From lust to betrayal to outright treason, the deeper the descent into hell, the more heinous the sins of those who are present. Dante’s Inferno is not a standalone work, however. The first installation of the Divine Comedy trilogy — Inferno (Hell), Purgatorio, (Purgatory), and Paradiso (Paradise) — Dante details the allegorical journey made by himself, first through hell, then through purgatory, and finally to heaven under the guidance of the Roman poet Virgil. Despite the insightful and poetic nature of the two latter books in the Comedy, they are often ignored in the canon of Western literature in the face of the more famous and celebrated Inferno

I have read Inferno several times throughout my life. Despite my efforts to strive to be a ‘good’ person, reading Inferno for the first time caused me to wonder which circle of hell I would end up in after I expired. After all, when we think of death and the fear of what comes after death, it’s not really heaven that we’re afraid of, is it? It’s the fear that despite our best efforts, we’ll end up in the proverbial ‘bad place,’ whatever you want to call it. Regardless of one’s metaphysical views on the world and the universe, death always bears a sense of uncertainty with relation to what comes afterwards. This is why Dante’s Inferno is a pivotal work of poetry that has influenced so many later works. One of those works is Mad Men, a drama series set in the 1960s that delves into the tumultuous personal and professional lives of advertising executives at a New York City advertising agency. For me, Mad Men was never a show I could just put on in the background while zoning out on the couch — it’s just so thought provoking and deep, and it, in my opinion, should be held to the same esteem as classic, seminal works of literature. The setting and time period of Mad Men facilitate the exploration of themes such as racism, addiction, and American consumerism. However, what I found most fascinating was how sin and morality were portrayed through the lens of the protagonist, Donald Draper. The season six opener of Mad Men ‘The Doorway’ opens with a scene of Don on Waikiki beach in Hawaii. Don, who is engrossed in Dante’s Inferno, sits beside his wife, Megan, as she spends the day tanning on the beach. He opens the episode with a narration of the first few lines of Inferno

“Midway in our life’s journey, I went astray from the straight road and woke to find myself alone in a dark wood - ” 

The narration is quickly interrupted by Megan, who orders another cocktail before sparking a conversation with Don. He puts down the book and doesn’t pick it up for the remainder of the season, yet its motifs of sin and justice are present within not only this episode, but the whole season. The narration sets the morbid undertone of the episode, foreshadowing several deaths that occur throughout. Beyond this, Don’s sinful progression throughout season six mirrors Dante’s journey down the nine circles of hell. One could even argue that the entire show represents the slow moral decay of Donald Draper — a descent through hell. The opening credits even display a cartoon man falling out of a skyscraper and descending towards the pavement. 

Despite the brevity of their feature in the episode, it’s clear that the opening lines of Inferno captivate Don’s psyche and trigger thoughts of death and punishment deep within him. After arriving back to New York, Don looks out of his window onto the Manhattan skyline and hears the ocean sounds he heard in Hawaii, sounds which he later admits remind him of death. His main task for work that week is to create an advertisement campaign for Sheraton’s Diamond Head Hotel in Hawaii. The advertisement he presents to Sheraton ultimately ends up being a manifestation of his macabre state of mind: “Hawaii —  the jumping off point”. Subconsciously, the thought of death, suicide, and hell pushes Don to produce work that mortifies his clients and his colleagues. He is scolded by his fellow partner Roger Sterling in particular, who reminds him, “We sold actual death for 25 years with Lucky Strike, you know how we did it? We ignored it.” 

The reason for Don’s existential crisis remains unclear until the last few moments of the first episode, when it’s revealed that Don is having an extramarital affair with his neighbor Sylvia, wife of Dr. Rosen. This is neither the first or the last affair that Don engages in throughout the series. Yet the shamelessness in sleeping with Sylvia merely minutes after speaking to her husband speaks to Don’s lustful desire and his pursuit of carnal pleasures. He is no longer a man who cheats on his partner when the opportunity arises, he goes out of his way to sin. He descends from the first circle of hell, a moral limbo, and progresses to the second circle of hell, sealing his fate as a debauched adulterer. 

Yet Don fosters a complicated relationship with his feelings of guilt towards his affair. He keeps seeing Sylvia, but reacts negatively to his actor wife Megan informing him of her upcoming ‘love scene’ in a television show. He’s visibly uncomfortable by the news and explains “Honey I can tolerate this but I can’t encourage it”. The shameless hypocrisy on Don’s part is clear and evident and leads him further down the path of moral decay. His unsuspecting wife tries to lighten the mood by asking him, tongue-in-cheek, “Would you still love me if I was a lying, cheating whore?”, not knowing that it was in fact Don who is guilty of just that.  

The deepest circle of hell in Dante’s Inferno is reserved for those who have committed treachery. Don’s affair with Sylvia is hardly the first instance of his infidelity in the series, but perhaps his betrayal of Megan with Sylvia is the most brazen of all. Megan here represents a youthful and innocent figure, unblemished by life’s turmoil. The opening scene contrasts the youthful carefree figure of Megan tanning on the beach with Don’s stoic, serious expression. Megan, chirpy as ever, is sporting a bikini and drinking her second blue cocktail whilst Don reads Inferno. Don doesn’t just cheat on Megan and betray his marriage; he betrays her innocence and trust in him. It is perhaps ironic that it was Sylvia who recommended Inferno to Don to begin with, and when she asks him of his thoughts on the book, he replies coldly, “It reminded me of you.” 

The series begins with Donald Draper as a morally ambiguous character. He refuses to expose his colleague Salvatore’s sexuality in a time when homophobia was rife within American society. He even supports his then-secretary Peggy when she falls pregnant and allows her to keep her job. Yet, Don also commits numerous sins in the early seasons. Initially, the grayness of his moral compass is subtly blamed by the show on his rough upbringing and lack of guidance. He is portrayed as somewhat of a ‘good guy, bad circumstances.’ As the series’ protagonist, the viewer is always rooting for Don, hoping he can turn his life around. When he divorces his first wife, Betty, he begins a process of meditation and self-reflection, where he laments the so-called “catastrophe of [his] personality” through the words of the American poet Frank O’Hara. His subsequent marriage to Megan seems to represent a new start for Don, a new era where he can be honest and loyal to his young wife. However, I believe the underlying purpose of Mad Men season 6 is to demonstrate the tragedy of Donald Draper. It doesn’t matter who he is married to, it doesn’t matter how self-aware he becomes, Don can’t help himself. Plagued by guilt at his constant betrayal of Megan but unable to stop his affair with Sylvia, Don is in moral freefall, descending into metaphorical hell. However, unlike Dante, Don has no guidance in his journey, he has no Virgil to guide him through hell and out to paradise. He’s going to hell.

Senote Keriakes is an Egyptian-Australian dentist and writer. He writes about whatever piques his interest but focuses on history, language and philosophy. Follow him on Instagram: @senote.jpg

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