10 Best Don Draper Episodes of 'Mad Men,' Ranked

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Jon Hamm as Don Draper in Mad Men sitting in a chair in his office with a cigarette in his hand. Image via AMC

Michael Block is a 14 time GLAM Award nominated writer, producer, and host of the podcast Block Talk. Throughout his time in the entertainment industry, he has worked on and off Broadway as a stage manager, written several produced plays, critiqued hundreds of theatrical performances, drag and cabaret shows, and has produced events randing from drag competitoons to variety concerts! 
On Block Talk, he interviews nightlife personalities, covers the wide world of entertainment through features, ranking episodes, and recaps ALL of Drag Race, as well as Dragula and Survivor. He has interviewed hundreds of RuGirls that span the globe at DragCon NYC, DragCon LA, and DragCon UK. 
In his free time, he makes one-of-a-kind jewelry and gift baskets with his mom. He is a proud member of the LGBTQ+ community. 

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One of the greatest television series of the 21st century is AMC's extraordinary period piece, Mad Men. Following the men and women in 1960s New York who occupied the glamorous yet morally complex world of Madison Avenue advertising. Exploring themes of identity, sexism, racism, consumerism, and the cultural shifts of the era, the series became a wonderful character-driven vehicle for a brilliant cast.

With a large ensemble, Mad Men was led by the incomparable Jon Hamm as Don Draper. An intricately complicated man, Hamm's character was the beating heart of the series. With a hidden past and a love for creation, Don Draper was one of the greatest characters in dramatic television. Over seven seasons and 92 episodes, Don played a key role in the larger operation. With many essential episodes throughout the series, these episodes stand out as the character's absolute best. Whether it was a momentous workplace event or a personal setback, these episodes were crucial to Don's rich journey. From pilot to finale, Don Draper was Mad Men.

10 "Shut the Door. Have a Seat."

Season 3, Episode 13

Jon Hamm as Don Drapper sitting and smiling in the 'Mad Men' episode "Shut the Door, Have a Seat." Image via AMC

Let's begin our Don Draper journey with the Season 3 episode, "Shut the Door. Have a Seat." Inspired by a line spoken in the episode and repeated in similar phrases throughout, the episode brings life-changing news to a variety of characters. Easily one of the most significant episodes of the series, the primary plot focuses on the key players at Sterling Cooper—Don, Roger Sterling (John Slattery), and Bert (Robert Morse)— convincing Lane Pryce (Jared Harris) to join them in leaving the firm to create their own. And along with them, they'd be taking the Lucky Strike account. With a litany of firings, including Lane's infamous, "I suppose you're fired," the episode marks a significant turning point in the story as the new company sets up the next chapter of Mad Men. The episode comes at a perfect time for the series, but truly elevates where Don goes next in his life.

With fast-paced dialogue and wonderful character development, "Shut the Door. Have a Seat" establishes the enduring bond among the core group. It serves as a reminder that these individuals are not just there for work; they have a vested interest in one another's personal lives as a means toward success. It gives our characters the chance to let their guards down for a grander purpose. For Don, the series was about his identity crisis and ability to forge a new life. The new firm allows him to start anew. The episode sees everyone rise to the occasion, becoming their best selves. It's the thrill of a fresh start. In proper poetic form, Betty Draper (January Jones) pulls the trigger on their divorce, allowing yet another new beginning to emerge for Don, despite his fight to hold onto something truly broken. At work, Don's in power. At home, he's lost the charge to Betty. It's a brilliant juxtaposition that reminds us it's impossible for Don to have it all at once. Now, as far as he and Peggy Olson (Elisabeth Moss) are concerned, his pitch to get her to join along is not a typical Don Draper business pitch; it's from the heart.

9 "Tomorrowland"

Season 4, Episode 13

January Jones as Betty talking to Jon Hamm as Don Drapper in the 'Mad Men' episode "Tomorrowland." Image via AMC

My, how a single season can mark a significant change for our characters. Such was the case for the Season 4 finale, "Tomorrowland." This episode watches as Don proposes to his secretary, Megan Calvet (Jessica Paré), after a trip to California with his kids. After a successful trip, Don ends up proposing to Megan, thus ending things with his girlfriend, Faye Miller (Cara Buono), over the phone. As Don's impulses lead him toward a new future, he's pulled back into his past when he returns to his old home for a poignant scene with Betty after her fight with Henry Francis (Christopher Stanley) over firing their nanny, Carla (Deborah Lacey). A wickedly profound portrait of Don Draper in a single episode, "Tomorrowland" continues to show Don as he strives for what he believes is stability in his life. Only, are his decisions truly leading him there?

Don had always wanted freedom, and when it came to women, his freedom was often too loose. Maybe it was a look at the time, but his womanizing was a flaw. During the season, after his separation from Betty, Don found a new woman, or two. The brutal blow from the previous finale was Betty's reminder that he'll always just be their children's father and nothing else to her. This proposal puts Don back on a mission for himself. A proposal isn't just for him, it's for him and his children. Knowing they took to Megan, she had to be the option for their tomorrow. The title is a clear reference to the main characters' desire to find a new tomorrow. Don is still struggling to find stability, but rash decisions continue to be his downfall. Yet, fearing he might be pulled back into his past, he was alone in the empty house with Betty, who gave him a key to their new place in Rye, which served as the conclusion to that chapter. It was a poignant and beautiful moment in Mad Men.

8 "The Jet Set"

Season 2, Episode 11

Jon Hamm in a car with a passenger in the 'Mad Men' episode "The Jet Set." Image via AMC

If there is one thing about Don Draper, it is that he sometimes enjoys marching to the beat of his own drum. Such was the case for Season 2's "The Jet Set." The episode watches Don as he abandons a business trip in Los Angeles to join a wealthy group of carefree nomads. A stark contrast to the hustle and bustle of life in New York, Don's responsibility-free romp in the sun serves as a tease for a hedonistic lifestyle. An existential episode for Don, "The Jet Set," forces him to explore what he really wants in life: to escape to a world of pure bliss or to realize that his greater purpose lies in a world of work and responsibility.

The episode is a brilliant juxtaposition of its visuals. Mad Men is known for its stark, clean lines and muted color palette. Alongside his new friends, Don sheds the mundane for a color-soaked world of wonderment. Part of why Don is pulled away is the fact that the nuclear war pitch at the aerospace conference became triggering. He's become entirely disillusioned by the end-of-the-world mentality of the time. His desire to jet set with the bohemians was all an illusion, though. He is tempted by Joy (Laura Ramsey), who has a perfectly fitting name. In the end, Don feels out of place, which is ironic since that was his initial basis in the world of advertising. "The Jet Set" serves as a stark contrast to the series, but it is integral for Don to know that his place is at the firm.

7 "The Suitcase"

Season 4, Episode 7

Elisabeth Moss as Peggy and Jon Hamm as Don asleep on the couch in the 'Mad Men' episode, "The Suitcase." Image via AMC

This episode is not only one of Don's best, but it's also one of Peggy's best. Let's discuss. "The Suitcase" follows the all-night work session between Don and Peggy, who bond while working on the Samsonite campaign. But beyond the work, the Season 4 episodes allow the pair to explore deep-rooted personal crises: Don's grief over Anna Draper's (Melinda Page Hamilton) death and Peggy's breakup with her boyfriend, Mark Kerney (Blake Bischoff). Set against the Muhammad Ali-Sonny Liston fight, "The Suitcase" is an episode in which emotional baggage comes to light as Peggy and Don's relationship continues to evolve into something profound.

"The Suitcase" is a wonderful episode that shows how work and play go hand in hand. That is, how personal lives can intersect and affect the work at hand. With the Samsonite deadline looming, the pressure is on, but both Don and Peggy understand they cannot simply remove their grief from the equation. Knowing bad news out of California about his stolen identity's wife is hanging over him, Don becomes belligerent. Knowing how she was forced to work and that she missed Mark's birthday dinner, which led to the breakup, Peggy becomes confrontational. With two emotional forces coming at one another, it reflects wonderfully against the boxing match. Yet, in the end, their different yet shared experiences of grief unite them through vulnerability, allowing for the breakthrough on the campaign to occur. Peggy and Don's ability to open up to one another in this manner marks a significant shift. The performances of Olson and Hamm are extraordinary, filled with emotional depth. "The Suitcase" is essential Mad Men viewing.

6 "In Care Of"

Season 6, Episode 13

Jon Hamm as Don Drapper shows his kids his old home on 'Mad Men,' episode "In Care Of." Image via AMC

The Season 6 finale was a rough one for Don Draper. "In Care Of" watches as his professional and personal lives implode. It all begins with Don and his career-defining moment with the Hershey's pitch. Abandoning the original pitch, Don opts to share a personal story about his traumatic childhood, revealing that he would steal Hershey bars as a child from the brothel where he grew up. The sudden pivot forces the company's hand, indefinitely suspending him, essentially firing him with no place to go. Meanwhile, after Sally Draper (Kiernan Shipka) is suspended from school for drinking, Don's frustration as a parent comes to a head. Hoping to ditch everything and escape to California with Megan, she decides to leave him. With everything seemingly ripped away, Don decides to share his past with Sally as they end up at his childhood home. Setting up a potential new beginning for Don in the show's final season, "In Care Of" showcases Don at his lowest only to know rock bottom isn't forever.

Mad Men has always been a narrative about honesty and integrity, where lies seem to be the best-case scenario for stability. Instead, Don grapples with the concept of radical honesty, which is incompatible with his advertising world, but important for maintaining relationships at home. Don has sought out the concept of the American Dream, but it's simply caused him ruin. In a universe where selling fantasies brings in money, Don no longer sees that as his final journey. He is ready to confront his past and bring change into his life, once and for all. We knew that Mad Men would lead Don to his moment, but how it was executed was brilliant. For Sally, it's a coming-of-age moment. For Don, seeing his daughter accept her future allowed him to own his past. A complete and utter game-changing episode.

5 "The Gypsy and the Hobo"

Season 3, Episode 11

Jon Hamm as Don Draper in a hat looking ahead in the 'Mad Men' episode "The Gypsy and the Hobo." Image via AMC

The truth always finds a way to come out eventually. We knew about Don's true identity, but Betty didn't. That was until the pivotal Season 3 episode, "The Gypsy and the Hobo." After Betty discovers the mystery of "Dick Whitman" in a shoebox, Don is forced to reveal everything. The major revelation forces Don's hand, leading him to decide that honesty is the best policy. Despite her complete shock, Betty decides in that moment not to abandon Don. The transformative conversation gives Don a glimmer of hope that their marriage has a future. Mad Men is a series about truth and deception through the guise of identity. This episode finally showcases the potential fallout when the past catches up with Don.

Don Draper is the ultimate showman, so when he reveals his story about identity theft and the struggles he endured during childhood, it was up to Betty to determine whether or not she was being sold a fantasy once again. Don reveals the truth about his mother and the reason he took on the identity of the real Don Draper, but it all culminates in discussing his half-brother, Adam Whitman's (Jay Paulson), suicide as a result of pushing him away to keep his own security safe and salvage a reputation. Don truly was shocked to learn that Betty ever loved him. There was a glimmer of hope at that moment for Don. But, for Don, that's always short-lived, as he's a man of his own vices.

4 "Waterloo"

Season 7, Episode 7

Jon Hamm as Don Draper sits between two colleagues at a meeting in Mad Men episode Waterloo. Image via AMC

There's always something magical about a mid-season finale. During the pre-binge full-season drop, our water cooler moments come in the mid-season finale episodes that help establish the back half of the season. In the case of Mad Men, "Waterloo" helped audiences gear up for the show's ultimate conclusion. With Don Draper 2.0 in full effect, the seventh season saw Don live his truths, even if it went against the firm. Fearing he will lose his job at Sterling Cooper & Partners, Don proposes moving out west with Megan, but she declines, signaling the end of the marriage. Meanwhile, Cutler is more than eager to fire Don for breach of contract. Don ultimately thwarts Cutler's ploy, with the support of Roger, Bert, and Pete Campbell (Vincent Kartheiser). But that water cooler moment arrives as the live broadcast of the first Moon landing captures the attention of the nation, just as Bert passes away in his sleep, causing Don's status in the firm to be uncertain. A new deal is made, and the firm's future changes as the episode ends, with Peggy revealing that they won the Burger Chef account.

A fantastical episode with so much going on, including a closing musical number of "The Best Things in Life Are Free" as performed by Bert and a chorus of secretaries, "Waterloo" became an instantly iconic episode. Don has experienced grief often, and it tends to be tied to brutal moments in his career. Losing Bert, his one tried-and-true champion, signaled the end of an era for Don. He may not have been fired, but with the new setup at the firm, Don's forced to embrace the end of the beginning with the moon landing as a backdrop. For those who like things to be a bit surreal at times, Don's hallucination of Bert was spectacular to watch because it paints a happy image of his mentor.

3 "Smoke Gets In Your Eyes"

Season 1, Episode 1

Jon Hamm as Don Draper talking to someone off-screen in an office in the pilot of 'Mad Men.' Image via AMC

"Smoke Gets In Your Eyes" was where it all started. In the pilot episode of Mad Men, we meet the core characters of our favorite series. We begin with genius advertising executive Don meeting his new secretary, the initially meekish Peggy Olson, at Sterling Cooper. Working on a campaign to reassure their biggest client, Lucky Strikes, Don must work his magic to keep the client happy in the face of an ever-changing climate that shows medical research claims smoking is harmful. Pete almost botches the entire relationship with the client, but Don steps in with an epiphany with a tagline that saves the day. But on the side, Don cheats on his wife, Betty, with anyone in his path, including his girlfriend, Midge Daniels (Rosemarie DeWitt), and Rachel Menken (Maggie Siff), a consultant for a department store. Though she is part of his work and pleasure worlds, their inability to see eye to eye in the pitch meeting creates tension that could blow up with their wealthy client. While they eventually make up, she tells him she knows what it's like to be an outsider, implying that Don may be keeping something from everyone, including viewers.

A well-structured and captivating pilot, "Smoke Gets In Your Eyes" serves as an exceptional world-building episode that puts Don at the center of the action. Don is immediately captivating and charismatic. Though the reveal about Betty and his children doesn't come until the end, Don shows how mystifying he truly is. Until we learn that he is not an entirely great man, we believe the fantasy. And that's essentially the premise of Don's presence on Mad Men. The pilot pulled you in, but Mad Men kept getting better over time. Without this crucial episode, the journey of Don Draper could not have begun.

2 "The Wheel"

Season 1, Episode 13

The men with the projector in the 'Mad Men' episode 'The Wheel.' Image via AMC

Season 1 started off strong. It ended even better. In the season finale, "The Wheel," the firm works alongside Kodak on their new invention: the slide projector. As Don, under the watch of the new Head of Accounts, Duck Phillips (Mark Moses), works on a pitch, he uses photos his half-brother sent him as inspiration, only to learn that he had died by suicide by hanging himself. Utterly struck, Don changes his entire pitch, inspiring him to create a new Kodak Carousel presentation centered on the "power of nostalgia." The spiel is deeply impactful, moving Harry Crane (Rich Sommer) to tears, and Kodak instantly signs on. With jubilation in the air, Don promotes Peggy to Junior Copywriter before heading home to surprise his family for the holiday. Unfortunately, after Betty discovered through the phone bill that Don had been checking up on her therapy sessions, she took the kids, leaving Don in a dark and empty home, the exact opposite image seen in the final moments of the pilot.

The Season 1 finale is a wonderful indication of Don's journey throughout the season. It also helps to dictate where his future might head. What's ever-present about Don Draper on Mad Men, his ability to shape a fantasy by innately understanding others, is why Don is such a remarkable character. Flawed, yet remarkable. For a show about advertising, it's important to see Don shine, and, up until this point, this was his crowning moment. Though the best is about to come in our final entry. "The Wheel" represents what the series is based on. Like the pitch to Kodak, the theme of nostalgia gives audiences the same sense of nostalgia while watching the period piece. The retro tone may be foreign to some viewers, but Mad Men makes you feel as if you had experienced it.

1 "Person to Person"

Season 7, Episode 14

Jon Hamm as Don Draper sitting at a beach retreat in the series finale of Mad Men. Image via AMC

The series finale of Mad Men is near flawless. And I think most Mad Men fans would agree that we all sang out in unity that the show capped off in glorious fashion. To kick off the episode, Don learns that Betty has been diagnosed with cancer, urging her to let the children live with him. She rejects this, reminding him of the instability in his life. Looking for solace, he meets with Anna Draper's niece, Stephanie (Caity Lotz), who whisks him off to an oceanside spiritual retreat. Though it does not go off swimmingly as Stephanie is criticized in group therapy for abandoning her child, Don makes a call back to Peggy, who implores him to return as she's confident McCann Erickson would rehire him. Before making a decision, he opts to confess to many of his wrongdoings over the phone. Don explores group therapy himself, in which a speech by another attendee causes Don to break down crying, learning about his pain over feeling overlooked and unloved. The episode ends with one last pitch: the infamous 1971 "Hilltop" Coca-Cola television ad playing atop Don meditating at the retreat, with a smile coming to his face.

In the world of the series, it's implied that this infamous campaign was the final idea from Don. The moment, in essence, shows that Don has found his ultimate peace and inspiration by creating the "real thing" for Coke, unifying the world with love, just as he sought peace for himself. A genuinely sweet send-off for the seven-season series, culminating in inner comfort for Don, is how the show should have concluded. Whether you find the ending corny or not, it was the right way to complete Don's overall arc.

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Mad Men

Release Date 2007 - 2015-00-00

Network AMC

Directors Michael Uppendahl, Jennifer Getzinger, Scott Hornbacher, Matthew Weiner, Lesli Linka Glatter, Tim Hunter, John Slattery, Alan Taylor, Andrew Bernstein, Jon Hamm, Barbet Schroeder, Daisy von Scherler Mayer, Ed Bianchi, Jared Harris, Matt Shakman, Lynn Shelton
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