“The Jet Set” (Season Two, Episode Eleven)
Despite the show’s title referring to a New York address, “Mad Men” has never been able to resist the lure of the West Coast (indeed, with Megan and Pete now residing in L.A., it appears from the first episode of season seven that the show is officially bi-coastal). But that’s nothing to be feared: trips to California have been responsible for some of the most memorable episodes, not least with “The Jet Set,” the first time its characters headed cross-country. It sees Don and Pete in the City of Angels for an aeronautics convention, but in true Don fashion, he’s soon easily distracted, heading off for a drive, a party and some heat-stroke induced sex with the enigmatic Joy (Laura Ramsey). Directed beautifully by Phil Abraham (one of the show’s regular and best helmers), there’s a carefree, woozy feel to the Californian sequence that really gets to the heart of the appeal of Don’s dirty weekend (why he didn’t move over there several seasons ago truly puzzles us). But that plotline (and the killer cliffhanger, as he calls someone unknown and announces himself as Dick Whitman) are only one element in a stellar episode, that also sees Duck Phillips plotting for his British former employees to buy the agency, Roger impulsively proposing to much-younger lover Jane, and the rest of the office discovering that new hire Kurt is gay. Some of these picks include major events in the lifetime of the show, but some are just the series working at the top of its game, and this is one of those moments.
“Guy Walks Into An Advertising Agency” (Season Three, Episode Six)
Shocking moments of extreme violence have become a hallmark of cable drama, from “Oz” and “The Sopranos” to “Game Of Thrones” and “The Walking Dead,” but given the nature of the show, that’s not a well that “Mad Men” has gone to very often. The major exception comes near the conclusion of this episode, and the result is one of the most talked-about scenes in the history of the program, one that caps off an episode that’s superb throughout. Amid other plotlines — Sally, haunted by her grandfather’s death, is having trouble adjusting to her new baby brother, Joan’s scumbag husband has been passed over for promotion, Don meeting with Conrad Hilton — we see the arrival of British executives from PPL, to announce their reorganization. Lane, much to his displeasure, looks set to be transferred to Bombay, to be replaced by young hotshot Guy McKendrick (Jamie Thomas King). But at a celebration, a drunken typist at the helm of Ken Cosgrove’s new ride-on John Deere mower runs over his feet, virtually severing it, and suddenly the status quo is restored. It’s a brutal, shocking and darkly funny scene, and one very much in the spirit of the series in general: death and injury aren’t a result of preludes and build-up, as in so many other shows, but comes at random and sometimes in the silliest way possible. At the time, you can’t help but laugh (the joke-like phrasing of the title of the episode isn’t an accident), but it doesn’t laugh long: the callousness with which it’s announced that Guy’s career is over is shocking, and the way that Roger and co. joke about it is doubly so.
“Shut The Door. Have A Seat” (Season Three. Episode Thirteen)
In general, we’ve avoided picking out season finales here, even though the final episodes have a tendency to make sense of the season as a whole in a way that’s become deeply associated with the show. But we couldn’t possibly ignore “Shut The Door. Have A Seat,” which closes out the third season in a hugely satisfying manner, and remains the boldest and most impressive finale the show’s attempted to date. It’s always very exciting when a show rips up the status quo, and that’s exactly what happens here. With Sterling Cooper, and parent company PPL, up for sale again, to arch-rivals McCann Erickson, the future initially looks uncertain, until Don suggests a breakaway agency to Cooper, and then Sterling (Don making up with his friend, the pair having been on the outs for a while). As they convince Lane to fire them (in exchange for making him a partner in the new company), and lure away Pete, Peggy and other key personnel, it becomes the closest that “Mad Men” has ever come to becoming a caper movie — a plan so crazy that it... just... might... work. And work indeed it does, with the new agency, Sterling Cooper Draper Pryce (complete with an ass-kicking Joan, free of her husband now he’s gone to ‘Nam) starting to exist by the end of the episode. It’s fun, exciting stuff (and, when Don finally gives Peggy the credit she deserves and asks her to join him, even moving), but the professional triumph comes at the expense of the personal, as Don’s marriage finally implodes, and Betty heads to Reno with lover Henry in order to get a divorce. The scenes between Jon Hamm and January Jones here are bruising and powerful, and the one where they tell the kids that they’re separating is doubly so. The show’s handling of the JFK assassination itself, in previous episode “The Grown-Ups,” could have been better, but the seismic changes that take place in its aftermath probably couldn’t have been.
"The Suitcase" (Season Four, Episode Seven)
If there was an inevitability to this list, it was this one: “The Suitcase” has already become legend, considered almost as soon as it aired to be the show’s finest hour, and we’re damned if we can think of anything that’s surpassed it since (the cast were fans too: Jon Hamm told an interviewer “I’ve never ever worked on something and felt the way I felt after ['The Suitcase']." Something of a chamber piece (or ‘bottle episode,’ in TV terms), it focuses, to the exclusion of almost everything else, on what is almost inarguably the key relationship in the show: that between Don Draper and his protege/rival Peggy Olsen. Despite the two never striking up a romantic relationship (thank God), and their differences in later seasons, their friendship has been at the heart of the show throughout, and it gets its best-ever showcase in “The Suitcase.” Against the backdrop of the Sonny Liston/Muhammad Ali fight, Peggy is dumped by her boyfriend (not unhappily) and stays in the office to work on a pitch for Samsonite with Don. The pair have a tumultous evening of dinner and drinks, taking in an argument over Don failing to appreciate Peggy, the acknowledgment of her given-up child, a darkly hilarious appearance by Duck, who’s broken in an attempt to shit in Don’s office (he’s drunkenly stumbled into Roger’s instead), and the death of Don’s friend Anna (the real Don’s wife, and perhaps the closest thing, except for Peggy, he’s ever had to a friend). Both lead actors used it as their Emmy submission that year, and frankly, it’s rather staggering that they didn’t win -- their deft performances are the best they’ve ever given on the show, and a reminder that, just as Don and Peggy ultimately bring out the best in each other, Hamm and Elisabeth Moss are each other’s finest dance partners.