Often heralded as one of television's most brilliantly constructed dramas, Mad Men having its ending planned from the start.

Many of Don's most memorable lines, seemingly simple or even cynical at first glance, reveal layers of deeper meaning upon closer inspection. These pieces of genius dialogue written by series creator Matthew Weiner and his writers are more than mere executive quips and words to live by in Mad Men. They foreshadow character arcs, expose societal hypocrisies, and subtly unveil the man behind the carefully constructed facade.

10 “Nostalgia - It’s Delicate, But Potent.”

Mad Men Season 1, Episode 13, “The Wheel”

Some of Don Draper’s most memorable dialogue is in Mad Men season 1, and the Kodak Carousel pitch in episode 13, “The Wheel” is no exception. It’s a writing masterstroke:

“Nostalgia - it’s delicate, but potent [...] It’s a twinge in your heart far more powerful than memory alone. This device isn’t a spaceship, it’s a time machine.”

Mad Men season 1 establishes Don’s remarkable gift of gab, especially when working under pressure with the loyalty and faith of a client hanging in the balance. Draper's work in the Sterling Cooper boardroom also ties in beautifully to the influences and experiences around him, which are a constant inspiration for him as a creative.

Another layer of brilliance is introducing this theme of nostalgia within the context of a period drama - it really catches the viewer off-guard, especially with the added awareness that Don’s marriage is not as rosy as the nostalgic New Year’s photo he uses to tug at the heartstrings. Both the clients and the viewers think they are getting a slice of life from Don here, but just like the slippery feeling of nostalgia, it is a mirage. Nostalgia bleeds through key moments throughout Mad Men, so this early establishment of this theme is very nicely done.

9 “People Tell You Who They Are, But We Ignore It…”

Mad Men Season 4, Episode 8, “The Summer Man”

The best Don Draper quotes are the ones that hit the hardest in the context of his entire character arc. In Mad Men season 4, episode 8, “The Summer Man”, Don is feeling more self-reflective than usual as he tries to nip his drinking in the bud, shaken to his senses by his dear friend Anna’s death. The episode opens with Don journaling about his earnest attempt at self-improvement, humbling himself as his swimming sessions cast doubt over the physical fitness he has until now taken for granted.

Don reflects: “People tell you who they are, but we ignore it because we want them to be who we want them to be.” It makes sense that Don is engaging in a moment of introspection after his rock bottom and major personal loss, as well as his attempts to date - but, like many Don Draper quotes, it is a double-edged sword.

The frequent dual meanings in Mad Men are what make it such brilliant screenwriting.

Don is right about the willful belief in the facade that is present in many relationships in the show’s setting, but it’s also a massive projection of his own identity crisis and feeling unseen by other people. The frequent dual meanings in Mad Men are what make it such brilliant screenwriting.

8 “What You Call Love Was Invented By Guys Like Me…”

Mad Men Season 1, Episode 1, “Smoke Gets In Your Eyes”

Don’s cynical dialogue in the dinner scene with Rachel Menken packed one hell of a punch. This meeting is the clear highlight of Mad Men's series premiere because Don has met his match in Rachel, who sees right through his elaborately built facade. By trying to exert superiority over Rachel by scoffing at her romantic nature, he only hints at what is revealed later - that Don hasn’t had much love in his life at all, and that’s why it is unrelatable for him.

Don claims:

“The reason you haven't felt it is because it doesn't exist. What you call love was invented by guys like me, to sell nylons. You're born alone and you die alone and this world just drops a bunch of rules on top of you to make you forget those facts - but I never forget.”

Just these few lines encapsulate why Mad Men is a different kind of period drama - one which both engages in and subverts the 1960s status quo. Don Draper has to play the rules of the game to get to where he is, but his upbringing and his secret identity instill in him a profound sense of loneliness and alienation that disconnects him from others. This carries right through the finale, so to establish it so succinctly is seriously impressive.

7 “The Universe Is Indifferent.”

Mad Men Season 1, Episode 8, “The Hobo Code”

“The Hobo Code” is one of the best episodes of Mad Men season 1, pulling back the curtain on poor Dick Whitman’s childhood experiences. Simultaneously, Don is spending time with Midge and her beatnik friends smoking pot and listening to the end-of-record crackle. Don presents two sides of himself in this first season - the sentimental creative and the nihilist. If he presented the latter to Rachel Menken in the pilot, he emphasizes it further here. Don leaves his audience deflated with this speech:

“Well, I hate to break it to you, but there is no big lie. There is no system. The universe is indifferent.”

This cold statement is only further enhanced by Don being able to walk out of the foggy apartment with impunity while police are in the building, simply because he is complying with that same system, an accepted gentleman. This quote is great because it sums up the decidedly cynical view toward beatniks and hippies in Mad Men - it is a tough pill to swallow for Don that he is perceived as privileged because, unbeknownst to most, he grew up anything but.

6 “If I Collected More Than A Dollar, She'd Buy Me A Hershey Bar…”

Mad Men Season 6, Episode 13, “In Care Of”

Don’s major meltdown in a pivotal meeting with Hershey's is a striking moment in Mad Men. The timing of this is crucial - previously, Don has met a new low with a couple of terrifying Mad Men episodes, culminating in Sally walking in on his affair with (or “comforting”) Sylvia Rosen. This familial crisis comes to a head just when Don is about to move to LA for a fresh start with Megan, but first has to do his Hershey's pitch. It is an unprecedented disaster.

After telling a fake story of what he would have liked his childhood to be like, Don takes it upon himself to tell the executives the hard truth:

“I was an orphan. I grew up in Pennsylvania in a whorehouse [...] If I collected more than a dollar she bought me a Hershey Bar. And I would eat it alone in my room with great ceremony, feeling like a normal kid. It said sweet on the package - it was the only sweet thing in my life.”

Don's quote is so striking because of its contrast to the all-American ideal he previously painted for his hungry audience. This moment of authenticity is a self-detonation for Don - he had already won them over, but seemingly reached his breaking point living a lie. The incredulity of his colleagues and the clients, thinking it’s a stunt, echoes Don’s earlier comments about wanting to believe in a facade and not the ugly truth.

5 “Listen To Me - Get Out Of Here And Move Forward.”

Mad Men Season 2, Episode 5, “The New Girl”

Don’s candid advice to his protégé in a Peggy-centric episode is memorable for its signature duality. The aptly-titled episode “The New Girl” sees Peggy given advice from Bobbie Barrett about how to be a professional woman in a man’s world. Peggy isn’t the fresh-faced secretary anymore, but people still automatically assume she slept with Don to become a copywriter - the episode emphasizes the contrary, that Peggy and Don have an unspoken platonic bond that reverberates throughout the series.

The episode features flashbacks to Peggy lying in the hospital after giving birth, with Don visiting and saying:

“Get out of here and move forward. This never happened. It will shock you how much it never happened.”

Moving forward is not only about Peggy’s renewal, seizing her moment, and focusing on her career, but is also a projection of Don’s relentless locomotion. Don previously rejected his brother in Mad Men season 1, saying his life only goes “in one direction - forward”. Ironically, the path of destruction he carves is informed by the past he has not made peace with. However, Draper's advice to Peggy here is irable and heartfelt - he doesn’t judge Peggy for what has happened, but knows her potential and wants her to succeed. It is a light among Don’s more disappointing moments in Mad Men.

4 “It’s Easy To Give Up Something When You’re Satisfied.”

Mad Men Season 6, Episode 7, “Man With A Plan”

Don Draper is known for his inspirational quotes about universal life experiences and, of course, copy - but this quote, like all the best Mad Men quotes, speaks volumes about his vulnerability behind the creative powerhouse. When his affair with Sylvia reaches a breaking point and he cannot fathom being rejected by her, he quips: “It’s easy to give up something when you’re satisfied.”

Draper is in the business of communicating a need for consumption, which relies on the customer never being satisfied...

Sylvia then retorts, “It's easy to give up something when you're ashamed," the hurt and disgust clear on her face, with a fantastic performance by Linda Cardellini. This quote is brilliant, firstly because it speaks to Don’s familiarity with the topic. Draper is in the business of communicating a need for consumption, which relies on the customer never being satisfied. Further, he has his own addiction issues with alcoholism and extra-marital affairs.

Don's insistence on believing that Sylvia is simply fickle is telling. He had previously imposed a sexual power play on Sylvia to cultivate a dynamic where she needed him, as emphasized by his love of the “nothing else will do” line - instead, he made her feel humiliated and revolted, realizing it was his fantasy playing out and not hers.

3 “I Don't Want To Wake Up Pregnant.”

Mad Men Season 1, Episode 1, “Smoke Gets In Your Eyes”

This line from Don Draper to Pete Campbell in Mad Men's series premiere might seem like a throwaway line, but it is actually very clever. Pete is clearly sucking up to Don in this scene, and Don tells him to take it down a notch with this satisfyingly quippy one-liner that puts him in his place. However, on a rewatch, it’s even better when you consider that in this same episode, Pete started a brief affair with Peggy, who became pregnant with Pete’s child. It is just one example of how densely packed Mad Men’s premiere is with foreshadowing.

2 “People Want To Be Told What To Do…”

Mad Men Season 1, Episode 6, “Babylon”

Another commonly-touted inspirational copywriting quote of Don’s is “People want to be told what to do so badly that they'll listen to anyone”. However, while an advertising agency is an important part of the show, parroting Don’s seemingly sage advice is unintentionally ironic, since so many of his truths established in Mad Men season 1 fall apart. In this example, Don is trying to highlight that the public will buy anything to soothe them.

This is especially potent given the turbulent socio-historical setting of Mad Men, whose cast of characters feel a lack of control throughout the series. However, Don learns throughout his arc that transactional relationships are not sustainable. This is further highlighted with his infamous “THAT’S WHAT THE MONEY'S FOR” row with Peggy in Mad Men season 4. It demonstrates how even Don's most seemingly straightforward statements carry complexity, hinting at the lessons he has yet to learn and the eventual crumbling of his carefully constructed worldview.

1 “We’re Flawed Because We Want So Much More.”

Mad Men Season 4, Episode 8, “The Summer Man”

In a pivotal Mad Men season 4 episode, Don utters a line that underscores a core human truth - we often desire what remains just out of reach. This sentiment speaks to our inherent dissatisfaction. No matter what we acquire, we're rarely content. Don's pattern of wanting something intensely only to discard it once obtained highlights this struggle. His journey ultimately points toward the necessity of living in the present and appreciating what he has, rather than perpetually seeking more.

At its core, Mad Men is about Don.

As with many quotes in Mad Men, Don’s wording here mirrors other dialogue throughout the series. In Mad Men season 6, he accuses Sylvia of this exact behavior. While it may be partly true and there was no morally superior party in that affair, it is also a projection, highlighting that at its core, Mad Men is about Don. Indeed, one reason why Jon Hamm found the final Mad Men season difficult was because it came full circle to Don’s sense of isolation and dissatisfaction despite having, in Peggy’s words, “Everything, and so much of it”.