“Signal 30” (Season Five, Episode Five)
Every fan of the show will likely have a different favorite season, but for this writer, it’s the show’s fifth, as you might be able to guess from the three episodes that I’ve picked out from it for this list. Like many of the show’s finest hours, ‘Signal 30” is a focused character study that could have come from a literary short story rather than as part of an episodic TV drama, this time focusing on one of the show’s most divisive characters, Pete Campbell. After trying to fix a leaky faucet in his kitchen, Pete and Trudie (the always great, often undervalued Alison Brie) invite the Cosgroves and the Drapers for dinner, where Ken’s secret side-career as a sci-fi writer is exposed, and the faucet bursts, leading to Don essentially emasculating Pete by fixing it properly. Entertaining a client from Jaguar, Pete eventually cheats on his wife in a brothel (having abortedly flirted with a teenager in his drivers’ ed class), and is then challenged, hilariously and brilliantly, to a fight by Lane when the Jaguar client’s own extramarital excursions are exposed. Pete is a character almost unique in television history--he’s defined principally by his weakness, only dangerous because he has such a ruthless touch, and yet over six seasons, Vincent Kartheiser has managed to make him somehow sympathetic as well as just plain pathetic. Here in particular, he’s moving as he breaks down in the elevator to an unfeeling Don. Directed by John Slattery (who’s become one of the series’ most reliable hands), the script served as the last produced work by legendary “Dog Day Afternoon” and “Cool Hand Luke” screenwriter Frank Pierson, who was a consulting producer on this series -- he co-wrote the episode with creator Matthew Weiner, and passed away in July of 2012, three months after the episode aired, aged 86. You couldn’t ask for a better way to cap off an extraordinary career.
“Far Away Places” (Season Five, Episode Six)
As if to prove our point about Season Five, the very next episode after “Signal 30” proved to be pretty much another instant classic: “Far Away Places.” Following Peggy, Roger and Don over a single day in a cunning tripartite structure that warps time cunningly and unexpectedly, it might still stand as the structurally boldest moment of a series that’s never been afraid to break from formula (or, really, never quite established a formula). Peggy argues with boyfriend Abe, has an unsuccessful pitch with Heinz when she’s abandoned by Don, gives a stranger a handjob in a screening of “Born Free,” and discovers that new recruit Michael Ginsberg was born in a concentration camp. Roger, meanwhile, meets Timothy Leary at a dinner party, tries LSD with his wife Jane, and has a warm and candid conversation with her in which they decide to end their marriage (though Jane seems to regret it in the morning). Meanwhile, Don takes Megan out for the day to a hotel in Plattsburgh, which turns into a fight, which turns into Don leaving her in a parking lot, nearly ending their marriage before a passionate reconciliation. It’s the show’s take on “Pulp Fiction” et al, and gloriously done; each mini-episode has a slightly different feel and tone, but with a thematic and visual consistency to unite them (thanks, one suspects, to director Scott Hornbacher, and a moment now to acknowledge how remarkable the direction on the show is, given that most of its helmers are relatively little-known, at least for now). Best of all is a closing shot of Don in his office that, one suspects, could make a fitting final image to the series as a whole (at least on some YouTube supercut or something...)
“Commissions And Fees” (Season Five, Episode Twelve)
“Mad Men” is not a show, broadly speaking, where things happen. Obviously things do happen, but they’re low-key, internalized things (as anyone who’s ever watched one of the hilariously un-revealing ‘next week on “Mad Men”’ promos will know)--the show is one of slow-burn dealing with plot across a season that a show like, say, “Scandal” would get through in a single episode. But occasionally, a major event hits the show, as it does in “Commissions And Fees,” and it’s one of the many reasons we picked the episode out over so many of the other good options in the transcendent closing section of season five. Focusing principally on Jared Harris’ Brit-in-exile Lane Price, it’s the last time we see the character, because it opens with his mild embezzlement being discovered by Don, who fires him, and ends with him committing suicide in his office. Lane’s downfall, a combination of pride, financial mismanagement, and a reluctance to ask for help, had been brewing for a while, but most viewers hadn’t dreamed that he’d go as far as he does here. Then again, the knife twists on him for a while, not least in the moment when his wife (Embeth Davidtz) reveals that she’s bought him a Jaguar that they simply can’t afford. There’s a dark humor laced throughout (the Jag, previously deemed as ‘unreliable’ by others, fails when he tries to gas himself in it), but it doesn’t lessen the power as his body is discovered, glimpsed through the high window of his office: this is TV death done as upsettingly and suddenly as it happens in real life. There’s a loose cycle-of-life feel to the episode (Sally gets her first period, much to her terror), but it’s Lane’s death that lingers over the episode, and much of the series that’s followed since.
“The Crash” (Season Six, Episode Eight)
“Mad Men” is a show about the 1960s, but it’s really only recently become about the Sixties -- what we think of culturally as the 60s is exemplified mainly by 1967 onwards, and much of the show has dealt with the awkward transition from the world of 1950s suburbia to a more dangerous, counter-cultural time (see Roger Sterling post-orgy in the seventh season premiere). As such, drugs have been a late arrival on the show (see the acid trip in “Far Away Places,” but it’s always done them well, and that’s particularly true of the uppers-fuelled “The Crash,” the most experimental and weirdest moment of the underrated Season Six. The new merged company are facing severe overwork, and so Jim Cutler (Harry Hamlin) brings in his doctor to give the staffers a shot of vitamins and amphetamines to get them through a long weekend of completing work for Chevrolet. It’s the most formally experimental thing the series has ever attempted (props to director Michael Uppendahl for an excellent job here), walking a fine line and never making clear what’s a hallucination and what isn’t--it could be everything, or nothing, or somewhere in between. Even Sally, who’s emphatically not on drugs, has a very curious encounter when she comes across an intruder who claims to be Don’s adoptive mother. The episode proved highly divisive when it aired, with some finding it empty and pretentious, but further rewatches have made clear that it’s anything but. It’s simply great that a show like “Mad Men” can take a risk like this six years in, and we hope there are more to come like it across the final season.
Honorable Mentions: Of course, there's plenty more where that came from if you're looking for further "Mad Men" greatness. In season one, we're particularly fond of "5G," in which we meet Dick Whitman's brother, and finale "The Wheel," with the famous 'carousel' speech. Season two brought "Flight 1," which sees the death of Pete's father in a plane crash, "Six Month Leave," featuring the firing of Freddie Rumsen, and "The Inheritance," the haunting trip to see Betty's father.
In season three, opener "Out Of Town" sees Don and Sal head to Baltimore, while "The Gypsy And The Hobo" is another excellent Don-centric episode. Season four has the excellent "The Good News," as Don and Lane get hammered together and bond, the stunning "The Crysanthemum And The Sword," and "Blowing Smoke," featuring the return of Rosemarie DeWitt's Midge. Season five begins with the two-hour "A Little Kiss," and the devastating "The Other Woman," as Joan is pimped out to the Jaguar executive in exchange for a partnership. Meanwhile, season six's most memorable episodes include "Collaborators," in which Trudie finally kicks Pete out, the Martin Luther King-featuring "The Flood," "Man With A Plan," as Don's relationship with Sylvia becomes dominant, and the always-welcome trip to L.A. in "A Tale Of Two Cities," plus the finale "In Care Of," as Don finally has the meltdown that's been so overdue.