Why Mad Men Is the Show You Should Always Revisit

In the late ‘90s, writer Sarah Vowell contributed a piece to This American Life about her obsessive rewatching of Francis Ford Coppola's The Godfather. Vowell didn’t just revisit the film casually; she immersed herself in it, watching it repeatedly on VHS, often chipping away at it in fragments during her busy schedule. She recounted how, on a typical day, she might steal an hour between classes and work to watch the harrowing scene where Sonny Corleone meets his violent end at the toll booth or reward herself after completing a paper by indulging in Michael Corleone’s chilling act of violence against a police captain.

This reflection became the title piece of Vowell's book Take the Cannoli, as it perfectly captures the youthful struggle for clarity and conviction amid uncertainty. We often find unexpected insights and resolve in the unlikeliest of places—here, in a film depicting midcentury Italian-Americans entangled in a web of crime and moral ambiguity. As I’ve grown older, I find myself understanding Vowell’s impulse to engage deeply with The Godfather. For me, however, my cinematic obsession lies with Mad Men, a show I continually revisit or eagerly anticipate revisiting.

I’m not claiming that Mad Men is superior to The Godfather or asserting that it embodies the zenith of the Peak TV era. Life’s too short for those debates. What I mean to convey is that, for me, Mad Men represents the pinnacle of rewatchability—a source of unending pleasure that retains its potency, no matter how many times I cycle through its episodes.

Each time I revisit the series, the cool, enigmatic protagonist Don Draper comes across as increasingly flawed and, frankly, insufferable. I’m not here to delve into discussions about problematic antiheroes or rehash the complexities of Don Draper; either you resonate with him, or you don’t. Yet, each journey back into the narrative of Mad Men reveals deeper layers of sadness and humor, and different supporting characters emerge as unexpected stars. In my last viewing, I found myself captivated by Pete Campbell, whom I now consider one of the great protagonists in American fiction. Previously, I may have focused on Peggy Olson or Joan Holloway, but the beauty of the show is that while the characters remain unchanged, I evolve with each viewing.

As I grow older, I often find parallels between my life and theirs. The characters navigate a tumultuous decade, living out the same experiences while I grapple with the challenges of my own turbulent life. Sometimes, I align specific episodes with real-life seasons, seeking a deeper resonance—timing a rewatch of a Christmas episode like “Shut the Door, Have a Seat” to coincide with the actual holiday season. I once calculated Don Draper’s age in each season, pondering what it would feel like to be 41 in 1967; now, I’m older than Don ever was, leaving me feeling contemplative and somewhat melancholic as I listen to the hypnotic strains of “Tomorrow Never Knows.”

Of course, you could apply this rewatching philosophy to any series, but I am convinced that Mad Men is uniquely suited for it because of its explicit exploration of time's passage. Knowing the fates of characters like Pete, Joan, and Peggy offers a comforting perspective against the existential dread of living my own life in a linear fashion. In an era where new shows emerge daily, it’s easy to feel like a processing machine, merely churning out watched shows based on critic recommendations. However, as humans, we engage with entertainment for deeper reasons.

When you’re grappling with uncertainty—whether it’s deciding what to watch next or contemplating life’s bigger questions—returning to Mad Men can be a balm. Whether it's your first viewing or your fiftieth, each rewatch serves as a reminder that, much like that perfect cigarette you crave, your best viewing experience is always the next one waiting for you.