Weekly Best Of: The Top Ten Best Episodes of Mad Men

In honor of this Sunday’s finale, and by way of introducing a new weekly feature, Tangled Up in Wires is proud to give you our humble selections for the Ten Best Episodes of Mad Men (in chronological order):

5G – The first hours of Mad Men are compelling, but it’s “5G” where the show takes its first big turn. This is the episode where Adam Whitman shows up, box of sepia photographs in hand, looking for his brother. Instead, he finds an empty shell who wants to throw money at him and make him disappear, lest Adam destroy the careful construction that is “Don Draper.”  “5G” is the first episode to really explore why Don is the way he is, a point helped along by the part of the episode where Don misses a family photo shoot to see Midge instead. So much of what this show has done in its three seasons starts here and the scene where Don tries to pay off Adam is one of Jon Hamm’s finer moments.

The Hobo Code – If Dick Whitman is the hobo, then Don Draper is the dishonest man, one of the markings that young Dick learns from a visiting drifter in “The Hobo Code’s” centerpiece flashback. I don’t think it’s quite that simple, but this episode provides a pretty decent cypher for reading Don/Dick’s inner turmoil, self-loathing, and constant desire to run. Most people remember this episode for the flashback, which is a great example of this show at its most deliberate and thoughtful, each word loaded with meaning. They also remember the killer ending, where Don tells the Beatniks “YOU can’t go out,” before putting on his coat and walking past a police officer despite reeking of marijuana. And, of course, this is the episode where Salvatore became more than just a jokey, background character, as one of the lipstick executives comes on to him.

Indian Summer – Adam’s appearance at the start of the episode gives a brief moment of hope – the chance for reconciliation still exists – before “Indian Summer” cruelly snuffs it, and Adam, out. Meanwhile, Don is finally made a partner, but his secret gets out, as a spurned Pete finds the box of photographs, in one of the show’s best cliffhangers. This episode also gave us the first appearance of the Relaxisizer, hinting at the coming clash between the buttoned-down Eisenhower years and the sexual revolution coming just around the corner, while also giving Peggy her big breakthrough.

The Wheel – By the end of season one, we knew Mad Men was good. But until “The Wheel” no one knew just how good this show could be. Pete finally uses his connections to get the Clearasil account, Betty checks her husband’s phone bill looking for evidence of an affair and finds something far worse,  Don, ever the caring father and husband, doesn’t want to spend Thanksgiving with his family, and Peggy’s stomach hurts. No moment in this episode is wasted, no note missed. “I can’t talk to anyone – I’m so sad,” Betty tells Glen when she sees him at the supermarket in a line that could have been said by any one of the main characters. “Please tell me I’ll be okay.” If that’s not enough of a tear-jerker there’s Don’s now legendary pitch to Kodak, which reduces Harry to a sobbing mess and convinces the executives to cancel their other meetings. Don - the ultimate ad man – sells himself on the everyday joys of fatherhood and marriage, making the final gut-punch of an ending, it’s too late for him to manufacture that kind of life, hurt that much more.

Three Sundays – Set over the course a few weeks in early April and focusing on three parents struggling with the responsibility of adulthood, “Three Sundays” is an episode that one could spend hours unpacking and still only scratch the surface. Betty’s desire for stricter parenting causes Don to have to face what a bastard his own father was. Meanwhile, Roger looks at Margaret’s future life with her fiance while his own marriage continues its decline. But, of course, the real standout of this episode is Peggy, who deals with resentment from both the other secretaries and her own sister, while still coming to terms with giving up her child. Colin Hanks’ last line - ”For the little one” - is so ambiguous and loaded that it makes for a powerful conclusion. All that, plus the depressing end to the American Airlines saga and Sally Draper taking her first steps to adulthood by downing a cocktail make for one of the finest episodes the show has produced.

The Jet Set – It starts off normal enough. Don and Pete fly to L.A. to seek out new accounts and glad hand executives. They’re a little awkward in their new environment, but nothing too far out of the ordinary. Then Don goes to a presentation on rocketry, and military folk boast about their ability to bring about armaggedon. It’s enough to make a man want to run off with a strange, seductive woman and spend a day or two in a mansion that she apparently lives in with some other people. Who are they? Why are they so weird? What’s the deal with those kids? “The Jet Set” never answers those questions, leaving the possibilities frighteningly vague. Still the point is clear: Don Draper, this is your future. You can either run from your responsibilities and live a life of coupled luxury and alienation or you can own them. I’ve never been more scared, more engrossed, more swallowed whole by an hour of television quite like I was by “The Jet Set.”

Mediations in an Emergency – Mad Men’s weakest attribute is the way it can sometimes use its period setting a bit too winkingly. You can only see a character talk about health and science while smoking a cigarette so many times before it starts to feel a little tired. However, season two’s finale “Mediations in an Emergency” owns the time period and makes for an appropriately epic conclusion to one of the finest seasons in TV history. With the backdrop of the Cuban Missile Crisis and the threat of total annihilation hanging over everyone’s heads, our cast of characters soldiers on with their mess of personal crises. Pete, inspired by Don’s (insincere) words of encouragement, warns him of Duck’s plans to take over Sterling-Cooper, leading to theincredibly satisfying showdown in the meeting with Putnam, Powell, and Lowe. Meanwhile, Peggy comes clean to Pete about the child, after a season of him sweating over his fertility and her questioning putting her career abover her personal life. And then there’s Betty, who reacts to the news of her pregnency with the Don Draper Trifecta: cigarettes, alcohol, and casual sex with a stranger – all while your spouse is watching the kids. Betty and Don’s role reversal, and the final shot of them looking extremely unhappy, is one of the show’s emotional and thematic highpoints.

My Old Kentucky Home – What do you remember the most about this episode? Was it the intrguing introduction of Conrad Hilton, or Connie as he’s known in that episode? Or the more sinister introduction of Betty’s future beau, Henry? Was it Jane making a drunken scene and sighing “I really should have eaten something?”  How about Sally Draper, actually doing a little growing up (not coincidentally, it happens when both her parents are gone)? Was it the bizarre sight of Joan and Greg’s dinner party and the masochistic way it built tension while completely avoiding the elephant in the room? Or Peggy, declaring to Kinsey and his poser friends that she wants to smoke marijuana and her spine-tingling last lines to her secretary? Of course not. This is the episode that featured Roger Sterling performing a song in blackface at a country club, oblivious and unashamed, the very picture of disgusting, unrestrained priviledge.

Guy Walks Into an Advertising Agency – Stop me if you’ve heard this one before. The head of the secretary pool’s last day is interrupted by some visitors from the parent company across the pond. What are they there for? Is it, as the partners assert, to take a look at the American genius who is the heart of the ad agency and the key to the Hilton fortune? Could a move to Paris London be in his future? No, actually; it’s to introduce the charismatic British whiz-kid who is going to restructure the agency and move it into the 1960s. So bye-bye, old manager (who gets a lovely stuffed snake and two tickets to India), and hello brave new world, filled with caviar and children all that is good. Then a secretary runs over his foot with a lawn mower. A raucous, tense hour with one of the most bizarre twists in the show’s history, “Guy Walks Into an Advertising Agency” is the episode that officially put to rest any notion of a third-year lull for Mad Men and set-up the rest of the season without changing the status quo.

The Gypsy and the Hobo – Okay, that last line has all the subtlety of the end of Doubt. But, come on. This episode features far and away Jon Hamm’s best performance, as you can actually see the confident veneer of Don Draper melt off  his face, exposing the scared hobo inside. But I’m getting ahead of myself. The true vision of Matt Weiner’s feminist nightmare becomes clear when Betty talks to her father’s lawyer about divorcing her husband, who has been lying to her from the day they met and living under a false name and, oh yeah, has another wife. But he is a good provider and Betty has no other options but to ride it out. So she confronts him and, in a long sequence filled with the tension that comes from knowing that Don’s latest, possibly psycho conquest is sitting 50 feet away in the car outside, Don tells Betty everything. Add to that the Roger Sterling origin story and the incredibly satisfying vase smash we were all waiting for (as well as Greg’s Serlingesque ironic punishment) and you’ve got an absolutely killer episode.