12 Essential Mad Men Episodes (and 4 More For True Fans)

With the fifth season premiere of Mad Men in sight, if you need to catch up on past seasons, or are new to the show (but don't have time to watch all 52 episodes), here are my suggestions for three "must see" episodes from each of the first four seasons and a few "honorable mentions" if you want to drill a little deeper:

Season One

Babylon (Episode Six)

Why it's important:  Peggy's nascent copywriting skills emerge as she coins the iconic term "basket of kisses" after she and a group of secretaries complete a sampling of Belle Jolie lipstick colors.  Roger and Joan's affair is revealed.  We witness the first flashback to Dick Whitman's childhood and experience the birth of his younger brother Adam. Betty recalls her first kiss, with a Jewish boy she describes as "gloomy." The first cracks in Don's relationship with Midge emerge as he discovers she is also involved with a beatnik in the Village. 

The Hobo Code (Episode Eight)

Why it's important:  The distillation of Don's hardscrabble upbringing is explained - he's a "whore child" whose father is a "dishonest man."  Meanwhile, his step-mother is a god-fearing Christian who barely acknowledges him.  Pete and Peggy continue their affair and Peggy's copy for Belle Jolie is approved by the client, resulting in her being invited into Don's office for a celebratory drink. Sal acknowledges his homosexuality to one of the Belle Jolie directors, but declines his invitation to the man's hotel room. Don realizes that Midge loves another man but signs over a $2500 bonus check to her as he leaves. This episode also has a classic "Draperism" - "There is no big lie. There is no system. The universe is indifferent" and a famous line from his stepmother (in describing life): "it's fat in the middle, open on both ends and hard all the way through." No wonder the poor kid changed his identity.

Nixon v. Kennedy (Episode Twelve)

Why it's important:  Pete attempts to blackmail Don into making him head of accounts by threatening to tell Bert Cooper about Don's desertion from the Korean War.  Don displays what will become a pattern throughout the show and decides to flee, asking Rachel Mencken to leave with him to Los Angeles.  She demurs, and Don refuses to give into Pete's request.  Pete divulges Don's secret to Bert Cooper, who shows no interest in it and gives Don permission to fire Pete (which he does not do).  A flashback shows us the incident that resulted in Dick Whitman switching dog tags with a deceased Don Draper and assuming his identity.

Honorable Mention - The Wheel (Episode Thirteen)

Why it's important:  Contains perhaps the single most famous scene in the history of the show, the "Kodak Carousal" pitch.  If you want to skip the rest of this episode, just go on YouTube and watch that three minute scene, it's classic.  Otherwise, Peggy is both promoted to junior copywriter and gives birth to Pete's child (which also explained her noticeable weight gain during the season).  Don finds out that Adam committed suicide after Don snubbed him and, in the season's final scenes, the writers juxtapose Don's imagined life where the family spends Thanksgiving together, with his actual life, where he blew off Betty and her family and returns to an empty home.

Season Two

The Gold Violin (Episode Seven)

Why it's important: Jimmy Barrett tells Betty that Don and Bobbi have been having an affair. A flashback introduces Anna Draper and we learn that Don was once a used car salesman.  After purchasing a new Cadillac, Betty vomits in it on the way home from the party celebrating Jimmy's new TV show. Sal's wife feels unloved and unwanted by Sal when Ken Cosgrove visits for dinner. Roger intervenes in a personnel dispute when Joan fires Jane after discovering she snuck into Bert's office after hours.  This episode is a pivot point in the Draper marriage - from here on out, Betty will never again fully trust him and the disintegration of their marriage picks up substantial speed.  It also lays the foundation for Roger's eventual marriage to Jane. 

The Mountain King (Episode Twelve)

Why it's important:  Having escaped New York and left Pete at a convention in California, Don visits Anna and vents his frustration at ruining his marriage, expressing regret for the first time over his actions.  Don's self-awareness is bracing, he describes his attempts to claw his way into his own life and fear that he is alone in the world.  His visit to Anna is also interspersed with flashbacks to their relationship at the time Don met Betty. Meanwhile, Sterling Cooper agrees to be acquired by Putnam, Powell & Lowe, allowing Duck Phillips to angle himself into what he thinks will be operational control over Sterling Cooper.  Most disturbingly, Joan is sexually assaulted by her fiancé Greg in Don's office after hours. 

Meditations in an Emergency (Episode Thirteen)

Why it's important:  Don comes back and although he doesn't admit his infidelity, apologizes to Betty for being "disrespectful" toward her. Betty learns she is pregnant (the result of a one off liaison with Don while they visited her ill father) and, after engaging in some revenge sex with a guy she picks up at a bar, allows Don to come home. At the meeting to discuss the new direction of Sterling Cooper as a part of PPL, Duck tries to assert his authority, but is cut off at the knees when Don threatens to quit. This episode also has what is probably the second most famous scene in show history - an intimate and powerful scene between Peggy and Pete that takes place against the backdrop of the Cuban Missile Crisis and risk of nuclear war where Peggy tells Pete that he got her pregnant and that she gave the baby up for adoption.  A haunting image of Pete, alone in the office with a rifle in his hands, is followed by an equally difficult scene of Don and Betty at the Draper family table, awkwardly coming to grips with the fact that they are again going to be parents. 

Honorable Mention - The New Girl (Episode Five)

Why it's important:  Don and Bobbi get into a bad car accident and Peggy comes to their rescue.  Peggy's willingness to house Bobbi while she recovers and keep Don's secret is a key building block in their deepening bond.  Bobbi also imparts some words of wisdom to Peggy about how to succeed as a woman in the business world.  The character of Jane Siegel is introduced as a replacement for Joan as Don's secretary. 

Season Three

My Old Kentucky Home (Episode Three)

Why it's important:  Betty meets Henry Francis at a "Derby Day" party thrown by Roger and Jane Sterling. Don meets Conrad Hilton at the same party and they bond over their similarly trying upbringings and distaste for "old money" types who throw lavish parties for themselves.  This episode also underscores the deepening stratification in the office, where Pete, Ken and Harry are now closer to upper management, while Peggy, Kinsey and Smitty are working over the weekend to prepare copy.  At the office, they get high with one of Kinsey's college buddies. 

Seven Twenty-Three (Episode Seven)

Why it's important:  It does what great Mad Men episodes do - it explores the inner conflict and turmoil characters experience.  Here, the story is told almost entirely in flashback, beginning at the end result of what unfolds during the rest of the episode. Peggy is wooed by Duck Phillips to join him at Gray.  She declines, but ends up sleeping with him and feels guilty about it afterward.  Betty continues her flirtation with Henry, and purchases a "fainting couch" that she places in the middle of her family room, masturbating on it while thinking of Henry. Hilton won't sign with Sterling Cooper unless Don has a contract, which he initially refuses to sign.  During a drunken late night drive, he picks up a couple who drug and rob him.  He signs the contract after Bert, leveraging his knowledge of Don's secret past, reminds him that signing really means nothing because after all, "who's really signing" the contract? 

Shut the Door. Have a Seat. (Episode Thirteen)

Why it's important:  This episode is all about death and renewal.  The death of Sterling Cooper as we had come to know it over the first three seasons of Mad Men, as Don, Roger, Bert and Lane conspire to flee and start their own agency ahead of the impending merger with McCann.  The completion of Don's backstory, as we witness, along with young Dick Whitman, Archibald Whitman's death from a horse's kick to the head as he prepares to sell his wheat at market for next to nothing in an attempt to save his farm.  We see renewal in the recruitment of Pete and Peggy to the new agency, Joan's return to handle logistics and office management, and in the episode's closing shot, where Don, having ok'd Betty's temporary move to Reno to secure a divorce (with Henry and Baby Gene in tow) looks out to the open hotel room at The Pierre, where the new Sterling Cooper Draper Pryce Advertising Agency is busy at work. 

Honorable Mention - The Gypsy and the Hobo (Episode Eleven)

Why it's important:  Simply put, it's the worst day of Don Draper's life.  It's the day when he is confronted by his wife not about his infidelity, but about his manufactured past. The long scene between Betty and Don is as devastating and gut wrenching as you would expect, but once he's caught, Don does not try to hide his past and explains it with a poignancy that will be explained in Season Four, when he tells Anna that once Betty knew who he really was, she wanted nothing to do with him.  

Season Four

I wrote a full season recap for Season Four:
(http://scarylawyerguy.blogspot.com/2011/10/tomorrowland.html), but suggest these episodes if you're interested:

The Rejected (Episode Four)

Why it's important:  Pregnant with meaning and subtext, the writers reward long-time viewers with a great storyline around Trudy's pregnancy and the unspoken past affair between Pete and Peggy.  More broadly, it explores the theme of youth in the 1960s and Peggy's place in it, being hit on by a gay woman and kissing a man she meets at a house party.  Pete flexes his account management muscles by pressuring Trudy's father to agree to give SCDP more of Vick's Chemical Company's advertising business.  Don's secretary Allison is brought to tears during a focus group convened by Dr. Miller when elliptically referring to Don and quits. The end of this episode contains an amazing tracking shot as Peggy and her crew of young friends are entering the elevator outside the office and she catches Pete's eye as he stands with the older executives from Vick's Chemical.  Their glance is knowing and poignant, a mutual recognition that something that passed between them will never be again. 

The Suitcase (Episode Seven)

Why it's important:  One of the five best episodes of the entire series and one of the three most important, The Suitcase takes place on Peggy's 26th birthday, which, instead of celebrating at dinner with her boyfriend and family, she spends alternately fighting with, tending for and sharing personal information with Don, who won't let her leave work because he cannot stand to be alone to call California and hear what he already knows is true - his rock, his ballast, the "only person who ever understood" him has died - Anna Draper. The episode's denouement occurs in the wee hours of the morning, when Don sees the ghost of Anna Draper in his office, she nods approvingly at the passing of his oversight to Peggy Olsen and heads to the great beyond.  

The Beautiful Girls (Episode Nine)

Why it's important:  Strong social commentary on the plight of women in the mid-1960 and a harbinger of the struggles ahead.  Sally runs away from home and lands in Don's office, Dr. Faye shows she cannot be a mother figure (but Megan does - to great effect later in the season), Peggy finds a socialist rabble rouser to be pushy and aggressive, but also naive and paternalistic, and Joan ends up getting impregnated by Roger after a heat of the moment liaison that follows their being mugged on the streets of New York City. Oh, and the silent shot of Joan, Peggy and Dr. Faye in the elevator at the end of the episode, each lost in their own disappointment, is priceless.

Honorable Mention - Tomorrowland (Episode Thirteen)  

Why it's important:  It tees up Season 5.  Don uses Anna's engagement ring to ask Megan to marry him.  Betty whines about wanting a new life and Henry basically tells her to "grow up." Peggy lands a new account just when SCDP is on the ropes and gets lost in the undertow of Don's engagement (Joan is not impressed).