Mad Men is a critically acclaimed drama series that takes viewers on a captivating journey through the bustling world of 1960s New York City. At its heart is the enigmatic Don Draper (Jon Hamm), the creative director of a prestigious advertising agency, Sterling Cooper. During its entire broadcast, the series has produced numerous exceptional episodes that will undoubtedly have a lasting influence on the realm of television.
However, there are certain episodes that truly stand out, thanks to captivating character arcs and writing that consistently elevates the series, capturing its signature tone while taking viewers on an emotional rollercoaster ride to another level.
10 “In Care Of”
Season 6, Episode 13 (2013)
IMDb Rating: 9.1/10
In this episode, Don finds himself amidst the collapse of both his personal and professional life, prompting him to prepare for a shift in his surroundings. Meanwhile, Pete’s (Vincent Kartheiser) life is unraveling, all thanks to Bob Benson’s (James Wolk) interference. In the meantime, Ted (Kevin Rahm) and Peggy (Elisabeth Moss) reach their own conclusions regarding their personal relationship, particularly after engaging in a series of flirtatious and elusive sexual encounters.
This episode stands out as one of the exceptional ones, as it portrays Don and Pete’s decline while highlighting Peggy’s ascent, culminating in a powerful image of her gazing out of the corner office window. Furthermore, the season concludes with Bob Benson carving turkey, comfortably situated in the heart of the Holloway household. Undoubtedly, he emerges as the season’s primary victor, though his ultimate motives remain as enigmatic as ever.
9 “Far Away Places”
Season 5, Episode 6 (2012)
IMDb Rating: 9.1/10
Viewers witness the same day unfold from the perspectives of three individuals: Peggy, Roger (John Slattery), and Don. An incident during the Heinz pitch meeting prompts Peggy to reflect on both her career at SCDP and her relationship with Abe (Charlie Hofheimer) in her personal life. During a second incident on Don and Megan’s outing, Megan (Jessica Paré) starts to question whether she can balance a professional and personal life with Don or if she even desires any connection with him. During Roger and Jane’s (Peyton List) outing, a third incident unfolds at a party with Jane’s friends where an LSD trip can severely impact their marriage in a disastrous manner.
Both the writers and the characters of Mad Men were all about attempting new things in this episode. Some earlier attempts—some more successful than others—involved orange sherbet, LSD, and giving the show a Rashomon-style makeover.
8 “Guy Walks Into an Advertising Agency”
Season 3, Episode 6 (2009)
IMDb Rating: 9.1/10
The bosses arrive from London to restructure Sterling Cooper, and to ensure a more seamless visit, Bertram (Robert Morse) urges Don and Roger to resolve their conflicts and differences. However, when the Director and Chairman make their entrance, accompanied by the young and dynamic Guy Mackendrick (Jamie Thomas King), it is Guy who delivers a surprising announcement to the entire team. It turns out to be a day full of events for Guy in the office. Meanwhile, as Joan (Christina Hendricks) gets ready to depart from her job, her husband shares some unsettling news with her.
This episode of Mad Men was perhaps the most action-packed, filled with dark comedy, and baffling moments to date. Furthermore, the episode concludes on a heartwarming note as Don reassures Sally (Kiernan Shipka) about her poorly named baby brother, insisting, “We don’t know yet who he’s going to be.” This line holds profound significance and invites various interpretations.
7 “The Gypsy and the Hobo”
Season 3, Episode 11 (2009)
IMDb Rating: 9.2/10
In this episode, two women from Roger’s past resurface. The first is Annabelle Mathis (Mary Page Keller), a former lover from two decades ago. She now runs a business called Caldicott Farms, which specializes in supplying horse meat for dog food. The second is Joan, who reaches out to Roger seeking assistance in finding a high-paying job, given her husband Greg’s (Sam Page) uncertain professional circumstances. The episode also marks a pivotal moment in the series, as Don finally reveals his true identity to Betty (January Jones).
It’s evident that this episode was intentionally designed as a triptych, featuring three powerful women from distinct perspectives, showing the strength of Mad Men in empowering women. Furthermore, the episode also highlights Jon Hamm’s exceptional acting prowess as he brilliantly breathes life into the character of Don, rendering him with remarkable realism and power.
6 “Person to Person”
Season 7, Episode 14 (2015)
IMDb Rating: 9.3/10
The series finale sees Don’s journey culminate in California with Anna’s (Melinda Page Hamilton) niece, Stephanie (Caitlin Marie Lotz), where he reflects on what lies ahead in his future. In the meantime, Roger opts to wed Megan’s mother, Marie (Julia Ormond). Joan presents a business proposal to Peggy, who is gradually embracing her emotions for Stan (Jay R. Ferguson).
Mad Men, despite its expertise in portraying existential despair, has consistently featured a remarkable sense of humor. Furthermore, the episode’s shift in the genre was somewhat predictable. While fans have been engrossed in pondering the deeper significance of Don’s carpet stains, the show has covertly crafted one of the most gratifying romantic comedies of our era. Additionally, the episode serves as a highly satisfying finale, effectively bringing to a close the magnificent seven-season journey of the show while preserving its original tone and enduring beauty from the very beginning.
5 “Commissions and Fees”
Season 5, Episode 12 (2012)
IMDb Rating: 9.4/10
The episode sees Don discover Lane’s (Jared Harris) forged check, leading to the complete unraveling of Lane’s world. Meanwhile, the Francises are organizing a weekend ski trip, but Sally is reluctant to join them. Frustrated, Betty resolves that if Sally continues to be troublesome, she will send her to stay with Don and Megan, regardless of Don and Megan’s preferences. Hence, Sally’s stay with the Drapers only exacerbates the tension in their relationship as they continue to lead their separate lives during her visit.
The episode is regaining its composure as it approaches the season’s finale. After briefly delving into melodrama with storylines involving Pete and Beth Dawes (Alexis Bledel), Harry (Rich Sommer) and Paul Kinsey (Michael Gladis), the show has shifted back to its darker and more intricately woven narratives, focusing on unexpected consequences and their underlying causes.
4 “The Other Woman”
Season 5, Episode 11 (2012)
IMDb Rating: 9.4/10
Pete requests that Joan make an unthinkable sacrifice to aid in securing the Jaguar account, a decision that challenges her integrity in pursuit of a larger objective. Meanwhile, Peggy contemplates the idea that it might be the appropriate moment to seek employment elsewhere. Thus, Freddy Rumsen (Joel Murray) provides her with encouragement and assists in spreading the word about her job search. Megan is thrilled to receive a call-back for a stage play, but Don is just beginning to grasp the implications of this development.
The episode is clearly designed as a “message” episode, and the message it conveys is far from subtle: Regardless of women’s efforts to achieve equality, there will always be a tendency for men to objectify women to some extent, as this is ingrained in the way men perceive them.
3 “Waterloo”
Season 7, Episode 7 (2014)
IMDb Rating: 9.5/10
The Apollo 11 space mission is underway, casting a shadow over the lives of those connected to Sterling Cooper. Don and Peggy are gearing up for a pitch to Burger Chef, scheduled for the day after the historic Apollo Moon Landing. Meanwhile, an internal power struggle within the firm, involving Sterling and Cutler, leaves Don’s future uncertain and in jeopardy. The Francis family has house guests in the form of Betty’s college friend, Carolyn Glaspie (Kellie Martin). Sally takes advantage of their visit to explore and test her emerging sexuality.
“Waterloo” served as a remarkable conclusion to an outstanding half-season, and despite the divorce and death, it offered an unusually optimistic tone. It carried a sense of momentousness that could have easily served as a finale, yet it left ample room for further exploration.
2 “The Suitcase”
Season 4, Episode 7 (2010)
IMDb Rating: 9.7/10
In the episode which takes place on 25 May 1965, Don purposely postpones returning an important call from California because he anticipates it will bring bad news about Anna. Instead, he occupies himself by compelling Peggy to forgo her birthday dinner and work an all-nighter with him for a client. The evening turns out to be the first genuinely intimate moment the two have shared since Don visited Peggy in the hospital after she gave birth.
It’s a brilliant episode, quite possibly the best fans have witnessed in Mad Men, with its dialogue effortlessly shifting between moments of tragedy and sharp, dark humor. The fact that it’s also the most structurally straightforward and minimal episode of the season so far may not be a coincidence. “The Suitcase” becomes even more poignant and captivating by choosing to focus almost entirely on Don and Peggy, who happen to be Mad Men’s most complex and compelling characters.
1 “Shut the Door. Have a Seat”
Season 3, Episode 13 (2009)
IMDb Rating: 9.7/10
Don’s life crumbles as he receives news from Connie (Chelcie Ross) about the sale of Sterling Cooper, which results in the loss of the Hilton account. Upon sharing the news with Roger and Bertram, the three of them decide to strategize for their respective professional futures. Meanwhile, at home, Betty has requested a divorce from Don, a decision he is unwilling to agree to. However, with the guidance of a divorce lawyer, Betty has devised a strategy that will make it challenging for Don to deny her request.
The season 3 finale was undeniably outstanding. In a series known for its often contemplative and understated moments, this episode was a whirlwind hour of television that utilized every second of screen time, ultimately delivering a game-changing twist that left the series dramatically transformed by its conclusion.
