5 Essential Mad Men Episodes Everybody Should Watch At Least Once

People always talk about "The Sopranos" and "Breaking Bad" when it comes to great examples of prestige television, but frankly, I don't think people talk about "Mad Men" enough. Created by Matthew Weiner — who cut his teeth as a writer on "The Sopranos" before creating his own series — "Mad Men" is a searing, stunning portrait of life in New York City in the 1960s through the eyes of ad executive Don Draper, played perfectly by a then-unknown actor named Jon Hamm. (Since his time playing Don, Hamm has fully admitted he never thought going to book such a big role and was on the verge of quitting acting; the rest, thankfully, is history.) 

When we first meet Don, he works in Manhattan every day at the firm Sterling Cooper, headed by his colleague Roger Sterling (a wry, hilarious John Slattery) and the older advertising tycoon Bert Cooper (Robert Morse, who passed away in 2022). As the show continues, the firm changes, Don's personal life goes through some serious ups and downs, and years pass, giving modern audiences a unique insight into this fascinating American era.

Whether you've never watched "Mad Men" or you're trying to rewatch it on either HBO Max or AMC+, there's a lot of "Mad Men" to watch — 7 seasons and 92 episodes, to be precise. Though there were some heartbreaking cuts to winnow it down to five — including "The Gypsy and the Hobo," "The Wheel," and "Guy Walks Into an Advertising Agency," just to name a few — there five episodes are absolutely essential to watch when it comes to "Mad Men."

Julie Andrews once taught me that the beginning is a "very good place to start," and I've never forgotten it. But in all seriousness, you do need to start with the pilot, "Smoke Gets In Your Eyes," to fully understand "Mad Men." Not every show kicks off with a super-strong pilot, but "Mad Men" sets the stage immediately, introducing us to Don Draper in his preferred habitat — a dark, smoky bar — and watching as he lightly interrogates an employee about what kind of cigarettes he smokes. The reason for this becomes apparent later in a beautiful bit of setup and payoff, when, faced with new guidelines from doctors regarding the "health benefits" of cigarettes which mean ad agencies can no longer claim they're good for you, Don comes up with a perfect pitch for Lucky Strike cigarettes, his brand of choice: "It's toasted." 

Elsewhere, we meet new Sterling Cooper secretary Peggy Olson (Elisabeth Moss, then best known for "The West Wing"), her defacto mentor Joan Holloway (the smirking, brilliant Christina Hendricks), the squirrelly junior account executive Pete Campbell (a perfectly smarmy Vincent Kartheiser), and one of Don's important new clients, department store mogul Rachel Menken (Maggie Ziff). There's also, incredibly, a big twist in this pilot. Though we first see Don with his free-spirited girlfriend Midge Daniels (Rosemarie DeWitt), in the final moments of the episode he heads home to the suburbs, kisses his beautiful wife Betty Draper (January Jones), and goes to check on his two sleeping children. While this sort of infidelity was widespread in the 1960s, it's still incredible that Matthew Weiner saves this reveal for the very end.

Season 3 of "Mad Men" is home to so many incredibly vital episodes — including the aforementioned "The Gypsy and the Hobo," where Don reveals to Betty that his real name is Dick Whitman, and "Guy Walks Into an Advertising Agency," where a client gets his foot chopped off by a lawnmower. But if we're only prioritizing one episode, it has to be the season finale, "Shut the Door. Have a Seat."

Why? Because not only does this episode officially kick off Don and Betty's divorce — in the wake of the reveal that Don, née Dick Whitman, stole dog tags from the real Don Draper's corpse in the Korean War, as well as his litany of infidelities — but it also dissolves Sterling Cooper for something new. As "Shut the Door. Have a Seat." opens, we learn, along with the characters, that a fictional version of the real-life advertising firm McCann Erickson is completing a major acquisition that includes Sterling Cooper, sending our favorite ad men (and women) scrambling. By now, Peggy is a copy writer, and though she feels constantly let down by Don, he ultimately puts his ego aside and begs her to work for him by saying that if she refuses, he "will spend the rest of [his] life trying to hire [her.]"

Peggy and Don team up with Bert Cooper, Roger Sterling, the underappreciated Pete, and their newer colleague Lane Pryce (Jared Harris). Alongside Joan and a few others, they raid the Sterling Cooper offices in the dead of night before the sale officially goes through, before celebrating their hard-fought victory ... and their new firm. "Shut the Door. Have a Seat." isn't just a perfect "Mad Men" episode; it's a bona fide masterpiece.

One of the greatest TV episodes in the history of medium, the season 4 episode "The Suitcase" is "Mad Men" at its very best — which is particularly remarkable when you consider that it really only focuses on Peggy Olson and Don Draper. With the rest of the new firm (named Sterling Cooper Draper Pryce, after its four founders) tuning into the 1965 fight between Muhammad Ali and Sonny Liston, Peggy, who's supposed to be going on a date with her boyfriend, ends up stuck at the office with Don thanks to an approaching deadline for a pitch for Samsonite. 

Yes, "The Suitcase" is the episode that features one of the most famous lines in all of "Mad Men" — Don screaming "That's what the money is for!" at an aggrieved Peggy after she tells him he never thanks her for her work. But it's also an unbelievable two-hander starring two of television's greatest performers. The two work, argue, make up, work, argue, and make up all over again. When Jon Hamm lets Don's careful façade crumble in front of Peggy for the very first time in their platonic relationship, both characters level up. The fact that the episode concludes with Don waking up to learn that his only true friend, the real Don Draper's widow, Anna Draper (Melinda Page Hamilton), is dead is a testament to the greatness of "Mad Men" as a whole. On a lesser show, Anna's death would get its own episode and put Don through a melodramatic ringer. In "The Suitcase," it's just one of many things that happens to him during an awful day at work.

There are a lot of great "Mad Men" episodes in season 5, but we're skipping ahead to season 6 for its finale "In Care Of," largely because it unpacks the contradiction that is Don Draper to great effect. With Sterling Cooper Draper Pryce set to split its employees between New York and California, Don finds himself at a personal crossroads. After spending a full night in jail for beating up a preacher, he tells his young second wife and former secretary Megan Draper (Jessica Paré) that they should consider moving across the country to help bolster her acting career and let him start over on the West Coast. Elsewhere, Pete finds out his mother fell off a cruise ship and has been declared missing, and Peggy finds herself torn between two men — but again, the focus here is Don.

Still in New York, Don comes up with a pitch for Hershey's Chocolate that's unbelievable for a few reasons. First, he makes up a gorgeous, idyllic version of his childhood that the audience knows with all certainly never happened (Don grew up in a brothel). Then, changing gears, Don tells the company members about his real upbringing in a house of ill repute, where his enjoyment of Hershey's products depended on how much money he stole from the clients that visited said brothel. Don is forcibly asked to take a leave of absence, but this revelation changes him outside of work. The episode ends with him taking his children Sally, Bobby, and Gene Draper (Kiernan Shipka, Mason Vale Cotton, and twins Evan Londo and Ryder Londo) to the actual brothel where he grew up, finally coming to terms with his past.

Not every TV show sticks the landing with its series finale, but the "Mad Men" finale, "Person to Person," definitely does. With Don estranged from his family, "Person to Person" sees him try to mend fences with Sally, who's struggling under the weight of the revelation that her mother Betty is dying from terminal cancer. He's also in California, running away from anyone and everyone. Despite a dramatic phone call with Peggy where Don confesses a variety of misdeeds, which leaves her incredibly concerned and begging for him to come back to New York, Don goes to a wellness retreat with Anna Draper's niece, Stephanie (Caity Lotz). During a group therapy session at said retreat, he fully breaks down.

So is Don Draper "cured" of his bad behavior? Yes and no, and also, maybe. We watch all of the other characters find some semblance of peace — Roger goes to Paris with his new wife Marie Calvet (Julia Ormond), Sally reunites with her brothers, and Peggy finds love. We eventually revisit Don, who's meditating on a mountaintop in California before allowing himself the tiniest smirk. Then, in an incredible masterstroke by Matthew Weiner, the 1971 "Hilltop" ad for Coca-Cola — the one that hopes to buy the world a Coke — plays, not-so-subtly indicating that Don used his new enlightenment to sell soda. 

This is, frankly, the only way that "Mad Men" could have ended, marrying Don's craven devotion to capitalism with his attempts to find inner peace. Though people might debate it, the "Mad Men" finale is perfect.

"Mad Men" is streaming now on AMC+ and HBO Max.