In the smoky, sharply dressed world of Mad Men, Don Draper was both a mystery and a mirror—a man of immense talent and charisma whose inner demons made him impossible to fully love or loathe. As the creative force behind Sterling Cooper, Don was brilliant, seductive, and often deeply broken. He could sell anything but rarely find peace. These ten unforgettable moments show exactly why Don Draper remains one of television’s most compelling anti-heroes—a man constantly torn between reinvention and self-destruction.
#10: Don Steals a Dead Man’s Identity – “The Hobo Code” (Season 1, Episode 8)
Long before Don was Don, he was Dick Whitman—a poor, frightened farm boy from a broken home. In a shocking revelation, we learn that Don Draper isn’t even his real name. During the Korean War, he switched dog tags with his superior officer, Lieutenant Don Draper, who was killed in an explosion. With the real Don dead, Dick seized the opportunity to disappear and start over.
This moment defines Don’s core paradox: he is both self-made and an impostor. It’s a bold move that catapults him into a world of success, but it’s also rooted in fear and shame. He didn’t just change his name—he erased his past. This morally gray choice sets the tone for everything that follows. Don becomes a man constantly hiding from who he was, building a life on a lie even he can’t fully outrun.
As anti-hero origin stories go, it’s one of the most chilling. Don’s reinvention is impressive, but it also shows just how far he’s willing to go to bury the truth. It’s a decision that gives him everything—status, wealth, a new name—but at the cost of authenticity and emotional peace. From that point on, every moment of charm and success is shadowed by the lie he lives.
#9: Don Cheats on Betty—Again and Again – Multiple Episodes
Don Draper’s infidelity isn’t a one-time lapse—it’s a chronic part of his personality. Despite having what many would consider the “perfect” life—a beautiful wife, kids, and a prestigious job—Don repeatedly betrays Betty. From stewardesses to artists to client wives, his affairs are more than physical. They’re a symptom of his constant search for meaning, for escape.
One of the most painful betrayals occurs in Season 1 when Don has an affair with Midge, an independent artist who represents the kind of untethered life he pretends to scorn. Later, his relationships with Rachel Menken and Bobbie Barrett show that he craves women who challenge him—but he’s ultimately too emotionally unavailable to commit.
Each time he cheats, it chips away at the idea that Don is simply a man under pressure. Instead, we see the cold reality: he’s deeply damaged, and his compulsions hurt those closest to him. Betty is left to question her own worth, spiraling into despair and eventually confronting him in one of the most cathartic moments of the series.
What makes Don’s cheating so impactful isn’t just that it’s wrong—it’s that he knows it’s wrong and keeps doing it anyway. It’s a classic anti-hero move he’s not oblivious to his moral failings. He’s painfully aware—and does them anyway.
#8: Don Fires Sal for Being Gay – “Wee Small Hours” (Season 3, Episode 9)
Sal Romano, Sterling Cooper’s talented art director, is caught in a compromising situation with a male client. When Sal refuses to give in to the client’s advances and the client complains, Don’s response is shocking instead of protecting Sal, he fires him.
Don’s cold dismissal— “You people”—cuts deep. It’s a moment that reveals just how transactional Don’s morality is. Despite often being portrayed as a progressive thinker in a conservative world, Don’s sense of right and wrong often shifts depending on who’s in power and what serves him best.
Sal had done nothing wrong. He was harassed and stood up for himself. But in Don’s eyes, Sal’s refusal jeopardized business, and that made him expendable. It’s one of the most heartbreaking and infuriating moments of the series. It reminds us that for all of Don’s flashes of empathy, he can be ruthless when his image or ambitions are threatened.
This decision haunts Don’s character. It’s a brutal reminder that being a charming, complicated anti-hero doesn’t exempt you from bigotry or cowardice. It’s one of the darkest stains on Don’s moral record—and he never truly atones for it.
#7: Don Leaves His Children Alone on Christmas – “Christmas Comes but Once a Year” (Season 4, Episode 2)
After his divorce from Betty, Don is adrift—emotionally and physically. In one of the most quietly devastating moments of the series, he leaves his young children alone on Christmas while he goes on a bender, drinking himself into a stupor and waking up next to a stranger.
This scene is powerful in its mundanity. There’s no big explosion, no dramatic confrontation—just a man who fails to show up for the people who need him. Don’s daughter Sally is particularly affected. She doesn’t just miss her father; she begins to understand that he’s incapable of being reliable. The emotional gap between them grows wider, setting the stage for years of tension and miscommunication.
What makes this so painful is how real it feels. Don isn’t being malicious—he’s being selfish. He thinks his kids will be fine. But the emotional damage lingers. This moment encapsulates the tragedy of Don Draper: a man who wants to love and be loved but can’t get out of his own way.
It’s a defining anti-hero move—not through violence or betrayal, but through neglect. It’s in the moments when Don fails to act that his flaws scream the loudest.
#6: Don Lies About His Past to Anna – “The Good News” (Season 4, Episode 3)
Anna Draper, the real Don Draper’s widow, is perhaps the only person who truly knows and accepts Don for who he is—Dick Whitman. Their relationship is one of the most genuine and grounding forces in Don’s life. But when Anna is diagnosed with terminal cancer, Don chooses not to tell her the truth.
In “The Good News,” Don visits Anna in California, fully aware of her diagnosis. He smiles, laughs, shares old memories—but never tells her she’s dying. It’s a deeply human and morally ambiguous decision. He wants to protect her, to preserve her happiness. But in doing so, he denies her agency over her final months.
This moment shows Don’s tendency to withhold truth under the guise of love. His lies aren’t always about manipulation; sometimes they come from fear, or the belief that he knows best. But it’s still a betrayal of trust. Anna deserved honesty. And Don, for all his charm, couldn’t give it to her.
When she eventually dies offscreen, Don is left adrift—his tether to his true self now severed. It’s a turning point in his emotional unraveling. Losing Anna is heartbreaking, but the way he avoids facing it is what cements his anti-hero status. He doesn’t just run from others—he runs from grief, truth, and himself.
#5: Don’s Meltdown at the Hershey’s Pitch – “In Care Of” (Season 6, Episode 13)
In what initially appears to be another brilliant Don Draper pitch, he presents a glowing, nostalgic advertisement idea to Hershey’s executives. He paints a picture of a perfect American childhood—buying a chocolate bar with his father after a Little League game. The room is impressed. It’s Don doing what he does best: selling dreams.
Then, without warning, Don unravels.
He pauses. Then begins to tell the truth—not the polished version, but the brutal, unfiltered reality. “I grew up in a whorehouse,” he confesses. “I’d take the money a man left on the nightstand, and I’d go buy a Hershey bar. That was the only sweet thing in my life.” The room falls silent. His colleagues are horrified. The executives are stunned. The pitch crashes and burns.
This moment is powerful because it’s one of the rare times Don chooses honesty over illusion. But it’s too much, too raw, and too late. What was meant as catharsis instead alienates the people around him. It costs him professional standing, trust, and nearly his job.
Don’s anti-heroism is never clearer than in this self-sabotaging moment. He reveals a truth no one asked for, knowing it will destroy his image. And in a strange way, it’s heroic. But it’s also reckless and selfish. He doesn’t consider the fallout. He doesn’t protect his team.
The Hershey pitch is a perfect example of Don Draper’s duality: a man who can make anything sound beautiful—until the truth slips out and shatters the illusion. It’s raw, painful, and absolutely unforgettable.
#4: Don Seduces His Therapist’s Wife – “The Forecast” (Season 7, Episode 10)
Even in the final season, when Don seems to be seeking redemption, he falls back into old patterns. One of the most uncomfortable examples is when he strikes up a connection with a woman at the diner—a woman who turns out to be the wife of his therapist. What begins as a casual flirtation turns into a calculated seduction, with Don sleeping with her while her husband is out of town.
What makes this moment so disturbing isn’t just the betrayal—it’s the total lack of remorse. Don has made progress in therapy. He’s begun to confront his identity, his pain, his past. And yet, when faced with loneliness and opportunity, he reverts to manipulation and self-sabotage.
This is anti-heroism in its rawest form. Don wants to be better, but he’s trapped in a cycle of self-destruction. His charm becomes a weapon, his vulnerability a mask. He takes what he wants, regardless of the consequences, and walks away unscathed—emotionally, at least.
But we, the audience, are left shaken. This isn’t the dashing Don Draper of earlier seasons—it’s a man running on fumes, repeating mistakes that have already cost him everything. The therapist’s wife is just another casualty in Don’s search for meaning through conquest.
It’s a moment that reminds us: for all his intelligence and evolution, Don still struggles to be the man he wants to be. His desires overpower his better instincts. And in the end, he’s still that same lost boy trying to fill a void that can’t be filled.
#3: Don Abandons His Family on Thanksgiving – “The Wheel” (Season 1, Episode 13)
In one of the most iconic and emotionally devastating moments of Mad Men, Don pitches Kodak’s new carousel slide projector. What he presents is pure poetry—he calls it “The Carousel,” a device that doesn’t move forward, but backward and around, like a time machine. As he speaks, photographs of his family flash onscreen: Betty smiling, the kids playing, snapshots of a life that looks perfect.
The room is silent. It’s one of Don’s best pitches. He moves everyone, including himself.
And then he goes home—only to find the house empty. Betty and the kids have gone to her family’s Thanksgiving without him. He was supposed to join them, but instead, he sits on the stairs alone, a man surrounded by everything he’s lost—or pushed away.
This moment encapsulates Don’s tragic brilliance. He can sell happiness, family, nostalgia—but he can’t live it. The contrast between the pitch and the reality is gut-wrenching. He’s moved to tears by images of a family he’s systematically alienated.
It’s not just that Don abandoned them—it’s that he didn’t even realize he had. He’s too consumed with image, performance, and control. The fact that he can make others feel so deeply, while remaining emotionally disconnected from his own life, is what makes him the ultimate anti-hero.
“The Wheel” is the soul of Mad Men in one scene—beautiful, hollow, and aching with everything unspoken.
#2: Don’s Breakdown on the Office Floor – “The Suitcase” (Season 4, Episode 7)
Widely regarded as one of the greatest episodes of Mad Men, “The Suitcase” shows Don at his most human—and his most broken. After a day spent bickering and bonding with Peggy, Don receives the call he’s been dreading Anna Draper, the only person who knew and accepted the real Don (aka Dick Whitman), has died.
Earlier, he had refused to answer the phone. He buried himself in work, pushing Peggy to stay late under the pretense of revising an ad. But as the hours pass, the truth creeps in. He’s avoiding grief, as always.
When he finally breaks down, it’s not in a grand gesture—it’s on the floor of his office, sobbing in front of Peggy. And Peggy, in a moment of quiet compassion, doesn’t say a word. She just sits beside him.
This moment is devastating because it strips away every layer of Don Draper’s myth. There’s no suit, no pitch, no woman to seduce. Just a man mourning the only person who ever really knew him. It’s the kind of raw, emotional honesty we rarely see from Don—and it hits with brutal force.
As an anti-hero, Don is often distant and inscrutable. But here, he’s just a man in pain. And in that vulnerability, we see both the weight of his deception and the cost of his isolation.
#1: Don Walks Away with a Smile – “Person to Person” (Season 7, Episode 14)
The series finale finds Don Draper at a crossroads. He’s left New York. He’s alienated his family, walked away from his career, and landed at a spiritual retreat in California, seemingly searching for inner peace. And for a while, it looks like he’s truly lost—broken, unshaven, sitting in lotus pose at the edge of the world.
Then, in the final scene, we see Don meditating. His eyes are closed. A bell chimes. Slowly, a smile spreads across his face. Then cut to black—and the famous 1971 “I’d Like to Buy the World a Coke” ad plays.
Did Don find peace? Did he achieve enlightenment and return to McCann-Erickson to create the ad? Or was it all in his mind?
The ambiguity is what makes it perfect. Don’s smile is both serene and eerie. Is it clarity or relapse? Peace or profit?
This final moment cements Don Draper as the ultimate anti-hero. He walks the line between transformation and manipulation, between self-awareness and selfishness. The audience is left wondering: Did he finally become the man he wanted to be? Or did he just find a way to sell peace like he sold everything else?
It’s a haunting ending that refuses easy answers. Just like Don.
Don Draper was more than a charismatic ad man—he was a walking contradiction. These 10 moments reveal how he constantly danced between redemption and ruin, truth and lies, love and loneliness. As an anti-hero, Don didn’t just reflect the darkness of the 1960s; he made us look at the shadows within ourselves. And that’s what made him unforgettable.
