Two Sides of the Same Damaged Coin

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The beautiful thing about staring at a train wreck, especially when you get the feeling that you can't look away, is that you get to do it from a distance.

Don Draper and Tony Soprano are not the most recent television antiheroes. They are not the best-written. Better Call Saul did more careful work with Jimmy McGill than Mad Men ever did with Don. Logan Roy was a sharper portrait of corrosive American masculinity than Tony ever was. And yet it is Don and Tony that people keep returning to. The Sopranos has had a full second-act cultural moment with viewers who were children when it aired. Mad Men reruns get the same treatment, just quieter. I want to understand why, and I think the answer has something to do with the kind of damage these two were allowed to have.

Beneath the stained veneers of success and power, we find two profoundly broken individuals, scarred by deeply buried wounds and an ongoing fear of rejection. Their charm is a flimsy mask for their pain, a desperate attempt to fill the void left by the women who were supposed to love them most. As we follow their journeys, we are confronted not just with the compelling drama of their lives but with the uncomfortable truth of their fundamental flaws and the pity they inspire. They are pathetic figures, in the older sense of the word, the sense that means worthy of pity. They are also charming, and that combination is what we keep returning for.

It All Has to Start Somewhere

The rejection from their mothers serves as a foundational undercurrent in both Don's and Tony's lives, influencing their actions and relationships in profound ways. For Don, the absence of maternal warmth begins with his biological mother's death during childbirth, an event Don imagines in almost comically tragic terms, and is sealed by his upbringing under a cold, abusive stepmother, Abigail. This profound lack of motherly affection is foundational to understanding Don's detachment and difficulty in forming genuine, enduring relationships.

If Don's maternal wound was an absence, Tony's was a presence. Livia Soprano was an ever-present and domineering figure whose influence reverberated long after her death. Tony invites chaos into his life and seems to crave it, mirroring the tumultuous nature of Livia's love.

Don's pursuit of shallow connection runs through his string of affairs, where each relationship serves more as a distraction from his inner turmoil than anything meaningful. His carefully curated persona of Don Draper, the epitome of twentieth-century American success, masks his true identity. Dick Whitman, a man he is continually at odds with. Don Draper is calm, clean, and collected. He lives in Ossining. Dick Whitman is tormented, messy, and emotional. He gets blackout drunk and punches pastors. Don, for all his professional triumphs, is haunted by an internal emptiness that no amount of acclaim or wealth can ever fill. At times he even seems to resent the success, hiding behind his love for the creative aspect of advertising, earnest as that may be. As he drifts further away from his manufactured ideal of what Don Draper should be, the facade begins to crumble, revealing the fractures within his persona. One of the reasons Don is so easy to crack is because he's not built on anything of substance.

Tony's experiences are indelibly marked by Livia's incessant coldness and the contradictory ways he perceives and interacts with her. He often describes her as a large and imposing figure, frequently dropping whatever he's doing to tend to her needs and engaging with her in the way a child might, his tone of voice shifting to a more submissive cadence when speaking to her. Yet in the same breath, he calls her this little old lady, revealing the complex and conflicting nature of their relationship. It is with a similar sense of uncertainty and self-doubt that Tony approaches most other aspects of his life, with one foot in and one foot out. He's a dedicated family man who can never be a devoted husband. He swore an oath of secrecy but opens up to a complete stranger in an office building every week. He's a hardened criminal who loses sleep over ducks.

The Impact on Their Worlds

The maternal shadows that loom over Don and Tony color their relationships, particularly with women, and dictate their engagements with society at large. Don, living a dual life as a con man and an ad executive, uses his charm as a strategic tool against true intimacy.

His engagements often follow a pattern. A compelling attraction, followed by a calculated emotional withdrawal once the relationship deepens, exemplified in his turbulent relationships with women like Rachel Menken and Sylvia Rosen.

He only likes the beginning of things.

This pattern underscores his deep-seated fear of genuine connection, rooted in the abandonment, the neglect, and the rejection of his youth.

Tony, inhabiting a more overtly brutal realm, wields his charm within the confines of his OC ties. His environment not only allows but often rewards emotional volatility. His raw, unfiltered emotional outbursts, from explosive anger to profound vulnerability, significantly impact his leadership within the DiMeo crime family and his domestic life. Episodes like Whitecaps, where Tony's rage culminates in a destructive altercation with Carmela, show how his emotional instability, fostered by maternal manipulation, permeates and dictates his closest relationships. The things that make him a god-awful husband make him an arguably competent mob boss.

Both men are actors on their respective stages, performing roles that demand a disconnection from their true selves. A protective mechanism instilled by early maternal rejections. This constant role-playing extends beyond personal interactions and affects their broader societal engagements. For Don, his crafted persona of a successful ad man both critiques and perpetuates the idealized post-war American masculinity. A facade that often leads to personal turmoil and self-loathing, as seen in moments of introspection throughout the series.

Both men grapple with their identities, and the dissonance between their public facades and private fears creates a psychological burden that is palpable in their moments of solitude and distress. Tony's panic attacks and Don's frequent flashbacks to his troubled childhood are manifestations of this ongoing inner conflict, a battle between the men they present to the world and the broken boys they hide within.

Their behavior on their children is its own indictment. Both men, as a consequence of their harsh upbringing, possess an aversion to violence within their child-rearing practices, though Don more vocally and in practice than Tony. AJ and Meadow Soprano navigate their father's criminal life and emotional unpredictability, shaping their worldview and moral compass. Sally Draper grows increasingly aware and critical of Don's inconsistencies and indiscretions, which influence her burgeoning sense of identity and ethics, a reminder of the far-reaching consequences of parental dysfunction. And Bobby, well, Bobby is going to grow up with all kinds of identity crises.

Shifting Power Dynamics and Elusive Control

The relationships between Don and Peggy Olson and Tony and Christopher Moltisanti offer compelling explorations of mentorship, power dynamics, and the challenges of navigating the gray areas of personal and professional boundaries. What begins as indifference between Don and Peggy evolves into a mentor-mentee relationship, morphing into a complex father-daughter bond, with Don serving as both a guiding force and a source of emotional support, at least within the scope of what he is able to provide. A heavy pour of Canadian Club and a daytime trip to the movies. As their codependency and emotional entanglement evolved, so did their sentiments of hostility and resentment, particularly when Peggy felt as though Don's ego was getting in the way of both her professional and romantic advancements, by way of Ted Chaough.

Throughout the series, Peggy's deliberate naivete, a narrative choice by the writers to withhold information from her, adds an additional layer of complexity to their relationship. As the series progresses, their bond oscillates between estrangement and reconciliation, with Peggy alternating between taking on the role of child in need of guidance, adversary in need of distance, and responsible adult daughter caring for her troubled father. It is only in their final scene together that the true depth of their connection is fully revealed, as Peggy's naivete falls away and she sees Don for who he truly is. A broken man in need of redemption. Even during that painfully expensive transcontinental phone call, much like a father talking to his child, Don is still fairly withholding while trying to be forthcoming. Don, the master of his craft, gives the client just enough of a taste to want more. He doesn't uncharacteristically tell her I'm Dick Whitman and I feel unfulfilled with the choices I've made. He gives her the eerie half-truth.

I took a man's name and made nothing of it.

But why does he do this? An inability to get all of these complex emotions out to arguably one of the last people in his life who will listen? An attempt to protect her from fully knowing the ugly truth about his true identity? Or was he just protecting himself? That is the mastery of the final episode and of the dynamic between Don and Peggy. It could be all of those reasons, and more importantly, it doesn't really matter.

In The Sopranos, the relationship between Tony and Christopher is a multifaceted exploration of family ties, professional ambition, and personal identity within the context of the DiMeo crime family. As Tony's nephew and protege, Christopher is caught in a constant struggle between his desire for recognition and advancement within the organization and his resentment of Tony's control over his life and career.

On one hand, Christopher's familial connection to Tony provides him with opportunities and privileges that other members of the crime family do not have. He is given high-profile assignments and is often protected by Tony's influence, allowing him to rise through the ranks more quickly than his peers. However, this favoritism also breeds resentment among other members of the organization, who view Christopher as undeserving of his status and see his success as nepotism rather than merit.

At the same time, Christopher's relationship with Tony is marked by a deep-seated desire for approval and validation that is often marred by an undercurrent of resentment and frustration. Christopher will occasionally have a difficult time reconciling whether he wants to model his life after his Uncle Tony or rebel against it. Having grown up without a strong father figure, Christopher looks to Tony as a surrogate parent and seeks his praise and acceptance. Even this dynamic is poorly defined for them, as they will casually alternate between a father/son, mentor/mentee, older cousin/younger cousin, and even sexual rival dynamic. This loosely defined emotional dependency creates a power imbalance, with Christopher often compromising his own desires and values in order to please Tony and maintain his favor.

On some level, Tony is cognizant of the fluidity of their relationship and is often able to manipulate it. That is also another point where the dynamics between Tony/Christopher and Don/Peggy intersect. The points in both shows where these relationships come to a head are moments when the domineering figures feel their control slipping. For Don, it is when he quite literally loses his power over Peggy as she chooses to leave the agency. For Tony, we see this theme throughout the series by way of Christopher's love affair with the film industry, which is highly allegorical to the wave of wiseguys flipping in the 80s and 90s, as well as his drug addiction. It will be Christopher's battle with substance abuse that becomes the ultimate death knell for their relationship.

The tragic conclusion of Tony and Christopher's relationship, with Tony choosing to end Christopher's life after a devastating car accident, stands in stark contrast to the more hopeful resolution of Don and Peggy's relationship in Mad Men. While Don is able to once again protect himself in the way he knows best, Tony too is forced to use the only card he had left in his deck when he realizes he had truly lost control over his nephew. He did not kill Christopher out of anger or out of mercy. He killed him because he realized that no matter what he did, there was going to be something with more control over Christopher's life than he had, and so in one final attempt to reclaim that power, he quite literally took it back with his own hands.

Why We Keep Going Back

Both shows have been off the air for over a decade. Mad Men finished in 2015, The Sopranos in 2007. In normal cultural physics, that is enough time for a series to fade into reverence, the kind of polite, library-shelf canonization that means nobody actually watches it anymore. That has not happened to either show. The Sopranos has had a full second-act cultural moment, much of it driven by viewers who were children when it aired. Mad Men gets the same treatment, just less loudly. People keep returning. I want to take that seriously as a question rather than a fact.

There are easier answers. The shows are well made. The performances are good. The dialogue holds up. All of that is true and all of that is insufficient, because plenty of well-made shows from the same era have faded. The Wire is more celebrated than watched. Breaking Bad gets quoted but not rewatched in the way The Sopranos does. Something else is going on.

My best guess is that Don and Tony are the last antiheroes from before the internet decided it had figured out the politics of masculinity. They were written, and watched, in a window where it was still possible to spend ninety-some hours of television with a damaged man without being required to render a verdict on him. Mad Men in particular trusts you to do your own work. It does not tell you what to think about Don. It does not punish him neatly. It does not redeem him in a way that lets you exhale. It puts him in front of you and waits.

The discourse around male antiheroes has changed since these shows ended. Some of the change is good. Some of it has produced television that is much more careful to instruct the viewer about how to feel. The villainous masculine figure now usually has a moral framework around him so the audience knows where to stand. Logan Roy is brilliant television and he is also accompanied, at every turn, by a chorus of characters and a structure of narration that keeps the viewer's judgment calibrated. The Sopranos does almost none of that work for you. Tony is in front of you. The ducks are in the pool. You are on your own.

I think the return to Don and Tony is partly nostalgia for that older bargain. Not nostalgia for the men. Nostalgia for the trust the shows extended to the viewer. The willingness to put unresolved damage on screen and let it sit there. The refusal to provide a clean moral framework. The refusal, in The Sopranos especially, to give you a final scene that tells you how to feel.

This is not entirely a flattering reason. Some of the return is also something less defensible, the way certain corners of the internet have tried to retroactively turn Tony into a folk hero, or Don into a coded role model for a kind of masculinity that the shows themselves were carefully critiquing. The shows did not endorse these men. The viewers sometimes do. That is a separate problem and the shows are not responsible for it.

But underneath the meme economy, there is a real audience returning to Don and Tony for the same reason a person returns to any difficult thing. Because the difficulty was the point. Because the unresolved ugliness was not a flaw in the writing, it was the writing. Because we are, twenty years later, hungry for something that does not tell us what to think about the worst people we have spent the most time with.

Wrapping Things Up

In the end, the stories of Don Draper and Tony Soprano serve as powerful reminders of the enduring impact our core relationships, or the lack thereof, can have on us, the complexities of the human psyche, and the masks we wear to navigate the world. Through their journeys, we are forced to confront the uncomfortable truths about the human condition, the fragility of our identities, and the ways in which our past shapes our present.

While their paths diverge in their final moments, Don finding a glimmer of hope in his connection with Peggy, and Tony truly letting go of his last shred of humanity, both characters leave an undeniable mark on our cultural landscape. They embody the antihero narrative that defined nearly twenty years of television, inviting us to grapple with the moral ambiguities, the shades of gray, and the unresolved questions that define our own lives.

The enduring legacy of Mad Men and The Sopranos lies in the way they hold a mirror up to society. Sure, you or I probably won't kill our nephews or steal another man's name. But those are things that happen, so obviously someone's out there doing it.

Maybe sometimes the screen just cuts to a Coke commercial.

And sometimes it just cuts to black altogether.