It’s remarkable to watch Jon Hamm, a decade after the finale of Mad Men aired on May 17, 2015, navigate the treacherous waters of Post-Iconic-Role Syndrome that other actors have drowned in. While the ghosts of Harry Potter and James Bond haunt Daniel Radcliffe’s and Daniel Craig’s subsequent work, Hamm has somehow managed to acknowledge Don Draper’s DNA while transcending it. Ten years after hanging up Draper’s perfectly tailored suit, Hamm is still selling. In Apple TV+‘s wickedly entertaining Your Friends & Neighbors, in which he plays a divorced, out of work finance guy who turns to stealing expensive goodies from his fellow residents of a tiny New York suburb, Hamm filches paintings and fences luxury watches with the same silver-tongued expertise he once applied to marketing cigarettes and Kodak carousels.
So there you have it: Hamm has gone from flogging the American dream to flogging the dreamer’s personal belongings. He wears his Mad Men heritage like a no-name vintage watch — stylish but not ostentatious, valuable but not defining. His character, Andrew “Coop” Cooper, carries himself with the same commanding presence as Draper, but there’s a weary knowingness behind the eyes now. Cooper is a man who has seen behind the curtain of American aspiration and found it lacking. Watching him dissect the psychology of the rich marks he targets — their insecurities, their desperate need for validation through stuff — feels like Draper’s confession after a decade of penance. And that confession was that after all the hard work, it’s just not worth it. From the first episode, Cooper articulates something Draper never comprehends: the hollow victory waiting at the pinnacle of American achievement. In the first episode of Your Friends & Neighbors, Cooper says, “You’re moving too fast to ask yourself those hard questions like, ‘When is it enough?’ and, ‘Really, what’s the point of all this s**t?’” “Empty people. Empty neighbors. Empty friends. That’s all we’ve got.”
The irony isn’t lost on the viewer: America’s most famous fictional adman has evolved into a character who can eloquently extol the Swiss craftsmanship of a Patek Philippe before dismissing it as nothing more than an overpriced bauble for the insecure rich. Hamm has graduated from a man who manufactured desire to a cynic who sees through it entirely, while still looking unreasonably handsome doing so.
As Hamm moves further from the shadow of Mad Men, one senses he’s not running from Draper but carrying him forward. It’s a character study in progress, evolving alongside America’s complicated relationship with wealth and fulfillment. After years staying present but removed with minor leads in the likes of Confess, Fletch and cameo turns in Baby Driver and The Morning Show, Hamm’s new starring role is the perfect character for our post-Succession, post-White Lotus cultural moment, in which the rich are portrayed not as glamorous titans but as morally bankrupt, emotionally stunted parasites. These shows have dismantled the myth of the deserving wealthy, revealing instead families such as the Roys, who are grotesque in their excess, pathetic in their insecurities, and ultimately hollow at their core. The ultrawealthy vacation-goers in White Lotus similarly expose the spiritual emptiness behind the back rooms of the health spa. It’s left us at a moment that aligns with Cooper’s cynical view of the wealthy as marks to be exploited rather than people to be admired.
Draper remains the eternal climber, frantically hoping that if he can reinvent himself enough, he can scale the economic ladder in an era when even advertising’s golden boys stand several tax brackets below today’s hedge funders. In Draper’s 1960s worldview, wealth still promises fun and dangles the carrot of hedonistic pleasure and status-driven validation. Meanwhile, Cooper has completed the full circuit of the American dream, winding up with a profound emptiness in having nothing left to need and nothing left to want. For him, the one real benefit is a philosophical detachment from the very desires Draper concocts.
Both characters operate as outsiders masquerading as insiders — Draper with his stolen identity selling the American dream, and Cooper with his hodgepodge criminal enterprise infiltrating his own elite social circle. However, where Draper seems genuinely tortured by his impostor syndrome, Cooper is liberated by his fraudulence. He moves through country clubs and gallery openings with the confidence of someone who knows the emperor has no clothes. Hamm delivers his character’s takedowns of luxury culture with such conviction that one could wonder if the actor has grown weary of the hollow prestige of a Hollywood career. (“A Rolex tells the same time as your phone, just less accurately and at 100 times the price.”) There’s a certain metacommentary at play when television’s most famous adman sneers at the aspirational lifestyle he once helped push, even post-Draper, as the voice of Mercedes, for which he earned a whopping $10 million. If Hamm is the American dream, Cooper is its post-recession, post-pandemic slump in which it reassesses what success and happiness truly mean.
Hamm’s trajectory from Draper to Cooper isn’t merely clever casting. It’s a story about America’s realization that its ultimate fairytale has all the substance of cotton candy. In doing so, he offers viewers the most un-American sentiment imaginable: perhaps having less is more. For a nation that’s spent centuries defining itself by what it owns, Hamm’s evolution feels like a perfectly timed reality check. One that even the greatest adman couldn’t sell.
Kara Kennedy is the royal correspondent for the Spectator World and writes the Substack Mom Wars.