The 20 Best Mad Men Episodes Ranked

Set against the backdrop of a 1960s America in which real, historical events are thematically relevant to our characters' arcs, Matthew Weiner's period drama "Mad Men" centers around a New York City advertising agency. More significantly, by following the lives of these (sometimes truly despicable) advertising executives, the show successfully interrogates the decade's social issues while simultaneously tracing rising feminism and shifting cultural ideals.

What propels "Mad Men" from good to award-winning is its impeccable use of dramatic irony — basically, the audience is always more aware than the characters — to present a rich portrait of the times, in which the old ways of '50s era Americana are starting to become archaic in an ever-evolving world. It pits a more progressive (but uncertain) future against outdated (and often bigoted) traditions of the past, and here we find the show's powerful narrative spine. We see the characters' hypocrisy reflected as they struggle with the images they present to the world and their own personal truths. Everything from authority to the illusion of identity is a performance, and our lead protagonist — the charming Donald Draper, who's hiding a dark past — is the series' biggest pretender.

And so, in celebration of this AMC drama's legacy, we've compiled a list of the show's 20 best episodes, ranked from good to great.

The narrative of "The Grown-Ups" traces the aftermath of a devastating national tragedy. Upon learning of President John F. Kennedy's assassination, our characters react in various ways. Roger's (John Slattery) daughter Margaret (Elizabeth Rice) is distraught over what the news means for her impending wedding. Kennedy's death throws Betty, who's still reeling from all she's learned about her husband's past, into fits of tears. Don, on the other hand, appears completely unaffected — emotionless, even. Compared to the reactions of others (their grief, sorrow, pain, and fear), Don comes across as eerily detached, which doesn't go unnoticed. On top of that, many of our characters — including the wedding guests who do still show up for the nuptials — glue themselves to the television screens, fixated on the news, essentially acting out the equivalent of modern-day doom-scrolling. 

But what's most impressive here, and what really makes this one of the show's best episodes, is that we find ourselves truly sympathizing with Pete Campbell, who we so often love to hate. And, for the earlier entries of "Mad Men," that's quite the narrative accomplishment.

In the summer of 1969, as the decade comes to a close, the advertising agency is faced with losing its coveted Chevy account, and the enigmatic Bob Benson (James Wolk) is offered an enticing opportunity with Buick. Envisioning an effective way to be seen as a "good family man," while also providing Joan and her son with security and stability, Bob uses this potential new job as an excuse to propose marriage. And, as Pete fights with Trudy over trying — and failing — to visit his daughter, Peggy prepares for a Burger Chef pitch by visiting several of the company's locations. Even after impressing her colleagues with her work, though, Pete would rather have Don close the deal.

It may not be as hard-hitting or emotionally compelling as other entries on this list, but by emphasizing the tension dwelling within our characters — and by bringing that disconnect between their core truths and their public images to the forefront of the narrative — "The Strategy" engages, quite effectively, with its overarching theme of identity.

Matt Zoller Seitz of Vulture believes the last two episodes of the first season fit together perfectly, claiming they "flow into each other, speak to each other, mirror each other. They are fully loaded, very different and yet complementary picture wheels." But where the penultimate episode depicts the power struggle between Don and Pete, "The Wheel" sees our characters, in the aftermath of election night and various poor decisions, coping with disappointment, disillusionment, guilt, fear, and nostalgia.

After Francine's confession regarding her own husband's infidelity, Betty ponders Don's faithfulness, and even considers peeking at the phone bill for answers. While she doesn't uncover an affair, she does discover a different — and still devastating — truth. A guilt-ridden Don discovers a devastating truth, too, when he tries to reach out to his younger brother Adam. Meanwhile, Pete uses familial ties to land a big account, and a newly-promoted Peggy (Elisabeth Moss), still unaware of her pregnancy, gets the biggest shock of her life.

The episode's most notable moment comes at the end, as Don pitches "the wheel" (a new slide projector) by presenting a slideshow of the life he's shared with Betty. In all these photos, he and Betty appear genuinely happy, but juxtaposed against the pair's tense, secret-filled marriage, the images are jarring, highlighting the tension between fantasy and reality, and foreshadowing the inevitable end of a relationship.

"Signal 30" was well-received by critics, with Emily St. James of The A.V. Club calling this mid-season 5 installment "transfixing and incredible ... a beautiful hour of television, full of powerful moments."

The episode opens with Pete sitting through a mandatory driver's education course and trying to get cozy with one of the college-bound attendees. Right away, we know this is going to be a Campbell-centric narrative, and right away, we're invested. From there, we see him in the throes of bitter jealousy, making a fool of himself. During the dinner party he and his wife Trudy (Alison Brie) are hosting, he discovers that his colleague and frequent rival, Ken Cosgrove, moonlights (quite successfully) as a science fiction writer. This exacerbates the tension between the person Pete is and the person he tries to be, ultimately culminating in quite the identity crisis.

According to Paste Magazine's Bonnie Stiernberg, while he's "easy to dismiss, [Pete is] one of the most complex, underrated characters on TV." As much as we may not really like Pete (he can be a despicable person, after all), he still manages to mesmerize us with a surprising amount of depth. As a result, we do, on occasion, find ourselves empathetic toward him.

Time's James Poniewozik declares this Season 3 entry a "sufficiently stunningly bloody episode to make up for several episodes of smoke exhalations and brooding looks." And, readers, he's not wrong. While it may not be "Sopranos"-level bloody, for a workplace period drama set in a tidy corporate New York advertising agency, it's practically a bloodbath.

Here, around Independence Day weekend in the summer of 1963, Ken Cosgrove (Aaron Staton) brings his riding lawn mower (let's call it Chekhov's Landscaping) into the office as the Sterling Cooper employees prepare for a visit from their British owners, who are in town to reassign and replace Lane Pryce (Jared Harris). Unfortunately, the potential new guy's arrival coincides with the office's farewell party for Joan, who, banking on her husband getting accepted into a medical residency program in the city, has formally resigned. At the party, things get ... well, unexpectedly gruesome.

The Season 6 finale, "In Care Of," is the only episode from its season to earn a place in the show's top 20. The narrative follows an increasingly unhinged Donald Draper: After spending the night in jail because of his brawl with a preacher, Don sets his sights on moving to California for a much-needed fresh start. His potential role as a West Coast representative for the company is also a great opportunity for Megan's acting career. It is L.A., after all. A successful pitch to Hershey's Chocolate is Don's way into this dream life, but things don't go as planned. Meanwhile, Pete and Bob butt heads in the professional world: After Pete blames Bob for his mother's presumed death, Bob finds a way to sabotage Pete's relationship with Chevy, securing the account for himself.

This episode is significant in that our lead protagonist sheds some of that Donald Draper armor, revealing an awful, heartbreaking truth about his past as the son of a sex worker to his colleagues. The honesty even extends to his children here, as we see him, in a moment of true change, willing to be vulnerable while actively working to overcome his identity crisis.

With its narrative focus on three relationships (Betty and Don, Joan and Greg, and Roger and Jane), Slant's Emily VanDerWerff argues that, thematically, this Season 3 entry is all about intimacy and uncertainty brought by a union built on a foundation of lies. Joan continues to clash with her physically and sexually abusive husband and his poor life decisions (like joining the army after an unsuccessful foray into psychiatry), while Roger has a surprising realization about his new wife, Jane.

By this point, we've watched nearly three seasons of ratcheting marital tension between Don and Betty, exacerbated by Don's dishonesty and infidelity, and by Betty's depression and loneliness. Here, we see this unhappy housewife finally confronting her ever-absent husband about all of his lies, and Don finally revealing his well-guarded secrets to the woman with whom he's shared the past several years of his life. This long-awaited scene does not disappoint. Both January Jones and Jon Hamm mesmerize in their perspective roles — Jones as the stunned Betty and Hamm as the vulnerable Don — as the characters sit across from each other at the kitchen table and have a real, honest, and ridiculously overdue conversation.

The A.V. Club's Emily St. James compares "The Other Woman" to one of the best "Sopranos" episodes: "Employee of the Month." But whereas "Employee of the Month" depicts the aftermath of a violent sexual assault and Dr. Melfi's moral battle as she debates asking Tony Soprano for an unethical favor, "The Other Woman" lays bare an unsavory truth about the male gaze and the constant objectification of women. It's everywhere — even in the workplace.

Here, Pete sees a chance to secure the sought-after Jaguar account when Herb Bennet, the head of the dealers' association, expresses interest in a night with Joan Harris (Christina Hendricks). When Pete first asks Joan to sleep with Herb, her initial reaction is one of appropriate shock and scorn, but that soon changes. What's particularly upsetting — and telling — about this storyline is that the men of the office, sans Don, don't see anything wrong with pimping out their female colleague for a business opportunity. Embezzler Lane even gives her advice on how to handle her incoming money.

"The Other Woman" is not shy with its cultural criticisms, and throughout the episode, we wonder if this is really who these male characters are. Ultimately, the unsettling narrative forces us to confront ugly realities about the world, namely the way some men objectify women for their own means, making it a tough but incredibly compelling watch.

In "Waterloo," which takes place in the middle of the show's final season and is set against the backdrop of Neil Armstrong's moon landing, Jim Cutler (Harry Hamlin) is out for Don's blood. Figuratively, of course. Even though these media-entrenched characters are often despicable in their own right (remember how we mentioned earlier that they're a reflection of the American hypocrisy of the time?), no one really gets whacked on "Mad Men." Aside from that lawnmower incident. That said, this narrative does feature the sudden loss of a character who's been with us since the beginning.

Citing Don's breach of contract, Jim tries to get him booted from the company, but Roger, Bert, and even Pete come to his aid. During this debacle, Megan points out that this would be a wonderful time for Don to finally move to the sunny West Coast, but he's determined to hold onto the career he's made as Donald Draper. Still, as a result of his currently murky professional status, he encourages Peggy to lead the Burger Chef pitch.

With its rich exploration of identity, "Waterloo" more than earns its place as the crème de la crème of "Mad Men." Don's hallucination of Bert singing "The Best Things in Life Are Free" while dancing with a group of secretaries is just the cherry on top!

The A.V. Club's Emily St. James believes "The Suitcase" is "one of the best episodes the show has ever done," and The Writers Guild Foundation describes it as "a great example of two unlikely characters opening up with each other and finding a weird, unexpected solace."

Using the looming deadline for an important Samsonite ad as an excuse to avoid returning an ominous phone call, Donald Draper throws himself into his work. Not wanting to be alone, he tries to compel Peggy Olson to join his impromptu all-nighter. And, despite already having plans (it is her birthday, after all), Peggy does, her decision coming at the cost of her boyfriend Mark.

This mid-season 4 entry examines the richly-layered (and always refreshingly platonic) bond between two of our main characters. National Post's Sadaf Ahsan attributes the success of the story to the fact that our "characters [are] laid so bare" here, and it's true. While not significant to the overall arc of "Mad Men," this storyline is vital in terms of character development.

In putting the entire narrative focus on Don and Peggy, the episode offers two carefully-crafted character studies, giving us a vivid sense of how these co-workers have shaped — and will continue to shape — each other's lives.