Mad Men: A Guide to Catching Up Before Season Five

Photo: AMC

Mad Men’s fifth season premieres March 25, which seems like a long time from now — unless you’re a newbie who needs to belatedly catch up on the entire series, in which case it is just enough time to do so. There are 52 episodes of Mad Men, and believe us when we say that you will inevitably want to watch more than one in a sitting. Pace yourself! Just like we did for Breaking Bad, here’s your Mad Men marathon training schedule. This guide is geared towards first-time viewers, but is also a perfectly effective schedule for those who want to relive the glory in anticipation of Don Draper et al.’s return. The show is on Instant Netflix, iTunes, Amazon, and DVD.

February 8
Episodes 1 and 2, “Smoke Gets in Your Eyes” and “Ladies Room”

Hard truth: Mad Men starts a little slowly. The first few episodes are really good, but they only hint at how good the show later gets; if these two episodes don’t grab you beyond “that was a pretty decent period drama,” don’t give up.

February 9
Episodes 3 and 4, “Marriage of Figaro” and “New Amsterdam”

This gets into the “mystery” of who Don Draper “really” is. Don’t worry about trying to Lost-style solve it based on clues in the show: Just pay attention to how different Don is depending on whom he’s talking to. Peggy, Pete, Rachel Menken, Midge, Betty: Everyone gets a slightly different Don. Of note: The actor who plays Glen is Mad Men creator Matthew Weiner’s son.

February 10
Episodes 5 and 6, “Five G” and “Babylon”

Things are heating up: Don’s excruciating back story comes to light, and he utters the line “I have a life. And it only goes in one direction. Forward.” Is this true of everyone else on the show? Something to think about! In “Babylon,” we get to know Peggy and Joan a little bit more, and each reveals an important truth about what motivates her: Peggy’s deeply afraid of being ignored or ordinary, and Joan’s afraid of being one-upped. More to think about!

February 12
Episodes 7 and 8, “Red in the Face,” “The Hobo Code”

For most viewers, this is when Mad Men turned from good to great. One thing this show does better and more than other shows is that it develops every character in the cast: “Red in the Face” is Roger’s big debut, and “The Hobo Code” gives us insight to Sal, Peggy, and Pete, too. Enjoy Rachel Menken while you can.

February 13
Episode 9, “Shoot”

One of the big themes of season one is perception: How do we see ourselves? How do other people see us? What’s a healthy attitude to have about your appearance? Betty becomes the embodiment of the various, insidious pressures women face — to be beautiful, to be content, to be the right kind of ambitious, to parent, to nurture, to subvert one’s own wants. The closing moments of this episode are Betty’s finest hour (and are visually perfect).

February 14
It’s Valentine’s Day! Do something.

February 15
Episode 10, “Long Weekend”

Ah, sex. This is the episode where things get particularly naughty, but we also get to see sex-as-catalyst in a few different ways here: what happens when you lust after someone you can’t have, the dangers of getting someone you shouldn’t have, and the frightening intimacy that comes from being with someone you genuinely care about.

February 17
Episodes 11 and 12, “Indian Summer” and “Nixon vs. Kennedy”

If you’re not fully on board for Mad Men now, just stop. (But how could that be possible?) These two episodes are all about our concepts of time. In “Indian Summer,” everything seems to be happening at the wrong time (like … an Indian summer), while “Nixon” creates a clear notch in everyone’s timeline: Things were one way before, but they are a new way now. Keep an eye on Harry here; he makes the same mistakes the people around him make, but he’s the only one who ever seems to feel bad about it.

February 18
Episode 13, “The Wheel”

Have tissues ready. Have many, many tissues ready. This is about as good a season finale as any show’s ever had: Don gives the greatest pitch of his career, Peggy gets some shocking (shocking! holy crap, shocking) news, and Betty confesses how lonely she is. What happens when we get what we’re supposed to want, but it doesn’t feel like enough?

February 19
Episode 14, “For Those Who Think Young”

Season two! Don reads the book Meditations in an Emergency in this episode, and it reappears later in the season. Go ahead and get yourself a copy. Also notice how Betty thinks really young — as in, does Betty sometimes just seem like a child, like Don says?

February 20
Episode 15, “Flight 1”

Families: Everybody’s got one. Pete’s is terrible, and Peggy’s is pretty brutal, too, but they respond to it in completely different ways. (Though both seek approval from Don, their stern father figure. Hm.)

February 21
Episode 16, “The Benefactor”

Do you like rough manual sex? Then this will be your favorite episode of this show.

February 23
Episodes 17, 18, and 19, “Three Sundays,” “The New Girl,” and “Maidenform”

Three episodes is a lot at once, but these are three terrific ones. Colin Hanks’ naive, guitar-playing priest lets us see a new side of Peggy — and it’s a side that Don would be really proud of, as she demonstrates in “The New Girl.” “Maidenform” centers on a bra pitch — Are you a Jackie or a Marilyn — but it’s not really about cup size. Even Don gets rattled by how quick people are to label one another. “Does it make you feel better to think that I’m like you?” he asks Bobbi Barrett. Well…isn’t he?

February 26
Episode 20, “The Gold Violin”

We’ve had episodes about sex, lust, perception, grief, and now, jealousy. Sal’s jealous of Ken, Betty’s jealous of Bobbie, Joan’s jealous of Jane, Don’s jealous of people who have a firm and real past.

February 28
Episodes 21 and 22, “A Night to Remember” and “Six Month Leave”

What do we sacrifice to “get ahead?” In “Night,” Betty thinks Don’s stepped on her one too many times, and in “Six Month Leave,” Peggy’s afraid that her success only comes from Freddy’s downfall. Both of them look to Don for guidance, which is almost never a good sign.

February 29
Episodes 23 and 24, “The Inheritance” and “The Jet Set”

These are two of the weaker episodes of the show, but don’t skip them completely: “Inheritance” has a scene where Don and Betty don’t say anything, but each take off their clothes, and just the sounds of the unzipping and ruffling create an incredibly tragic moment. “The Jet Set” isn’t great, but the closing moments are essential. Happy leap year!

March 1
Episode 25, “The Mountain King”

Poor Joan. Poor, poor Joan. There’s some Dick Whitman back story here too, but mostly…poor Joan.

March 2
Episode 26, “Meditations in an Emergency”

Did you read the book like we said? Peggy’s monologue to Pete perfectly flips their power dynamic from “Red in the Face,” and it’s one of Elisabeth Moss’s shining moments on the show.

March 4
Episode 27, “Out of Town”

Season 3, here we come. Don and Sal travel to Baltimore, but a lot of our central characters often feel like they’re from, well, out of town: Don’s an impostor in a lot of ways, and Sal is too; Pete chronically does not fit in, and Bert’s a wonderfully strange guy. This episode introduces new CFO Lane Pryce, who’s similarly out of his element.

March 5
Episodes 28 and 29, “Love Among the Ruins” and “My Old Kentucky Home”

The more familiar you are with the opening moments of Bye Bye Birdie, the better “Love Among the Ruins” will play. Pay special attention to Sally in “My Old Kentucky Home.” Someone should.

March 7
Episodes 30, 31, and 32, “The Arrangements,” “The Fog,” and “Guy Walks Into an Advertising Agency”

“You have everything, and so much of it,” Peggy tells Don in “The Fog.” It’s a jolt, and a solid moment where the show acknowledges how other people look at him not just with admiration or jealousy but also with a little bit of pity, knowing that he doesn’t know what he (seems to) have. “The Arrangements” is a sad, raw look at loss, and “The Fog” is a major departure for the show, by going too far into a dream sequence, but “Guy” turns out to be the most audacious episode of the series. Who said Mad Men wouldn’t do physical gags?

March 8
Episodes 33 and 34, “Seven Twenty Three” and “Souvenir”

Peggy! And…a new suitor! It’s surprising, but it’s hard not to be happy for her, at least a little bit. Betty and Don try to be new suitors themselves in “Souvenir,” and while of course it’s emotionally poisonous, it’s one of the most aesthetically pleasing scenes.

March 10
Episode 35, “Wee Small Hours”

Watch for Don’s reaction (or lack thereof!) to hearing “I Have a Dream.”

March 11
Episodes 36 and 37, “The Color Blue” and “They Gypsy and the Hobo”

Betty’s ongoing misery in her marriage comes to a head, and she confronts it as only she can: denial, and then explosive rage. “The Gypsy and the Hobo” echoes back to season one’s “The Hobo Code,” not just in the obvious hobo-presence sense, but also in the way Don chooses to articulate his personal history.

March 12
Episodes 38 and 39, “The Grown-Ups” and “Shut the Door. Have a Seat”

If season three had some weak spots — “The Fog” maybe — then “Shut the Door. Have a Seat” makes up for them.

March 14
Episode 40, “Public Relations”

Season four, now: the home stretch. “Who is Don Draper?” the episode asks. Literally, someone asks that question.

March 15
Episode 41, “Christmas Comes But Once a Year”

Say hello to Dr. Faye, season four’s best new character. (Except for Mrs. Blankenship, maybe.) This episode starts exploring the art of wooing, and how there’s no such thing as a guaranteed response: Don’s neighbor is a nurse, which he would hate but she loves; Peggy’s boyfriend assumes she’s a virgin, which she doesn’t correct him on; weird kid Glen starts chasing Sally, and his weird ways are weirdly compelling to her. Why do we like what we like?

March 16
Episode 42, “The Good News”

California-set episodes are divisive: Some people love the fresher, brighter side of Don, while others feel the story is maybe a little tangential to the central ideas of the show. The good news in this episode is that both sides are right!

March 18
Episodes 43, 44, and 45, “The Rejected,” “The Chrysanthemum and the Sword,” and “Waldorf Stories”

Don, the guy who can’t be known. Dr. Faye, the woman who can figure anyone out. Are these two a pair, or what? Peggy gets in more than her fair share of zingers in these three episodes, demonstrating not just her level of confidence, but the new level of respect the people around her now afford her. The poignant imagery of Peggy on the scooter in “Chrysanthemum” is topped only by the disorienting sight of Don sporting some seriously wide lapels in a flashback.

March 19
Episode 46, “The Suitcase”

This is arguably the best episode of Mad Men, and one of the best hours of TV in living memory. Congratulations, you have now seen it!

March 20
Episode 47, “The Summer Man”

This episode includes a very controversial voice-over from Don, which we hear mostly while he swims. Whatever water symbolism you’re thinking about — baptism? cleansing? drowning? — is applicable.

March 21
Episodes 48 and 49, “The Beautiful Girls” and “Hands and Knees”

Sally Draper is one of the more interesting kid characters on TV, and a huge part of that is due to how good Kiernan Shipka is. She’s not cloying or precious at all, and there’s a real intense darkness to Sally — which is rare to see articulated in a little girl. “Hands and Knees” illuminates why Sally might feel hopeless: Is she going to grow up to be like Joan (abused, ignored, sad) or Dr. Faye (a doctor, ignored, sad)? Or Betty (crazy, ignored, sad)?

March 22
Episodes 50 and 51, “Chinese Wall” and “Blowing Smoke”

Self-sabotage is the name of the game in “Chinese Wall.” Don’s an old pro at it, but Roger, Joan, Peggy, Peggy’s new boyfriend, Megan, Faye, and Pete all take turns on this episode setting themselves up for failure. “Blowing Smoke” digs deeper into the idea of failing, bringing back a long-forgotten character and showing Don and his partners in a real moment of professional crisis.

March 24
Episode 52, “Tomorrowland”

This is it: the season four finale. Other season finales offered a lot of closure or served as an exclamation point on the season as a whole. Not so here. “Tomorrowland” is very much about, er, tomorrow, the future, hopes, dreams, abandoning the past, etc., and what better place to do that than Disneyland?

Mad Men: A Guide to Catching Up Before Season Five