The challenge in "Key Episode"ing Mad Men is that it's basically the go-to example of a modern show which is structured like a series of novels (seasons) divided into chapters (episodes). Each episode of Mad Men contains arc advancement, and the episodes must be watched sequentially in order to be fully understood. Rather than watching an episode here or there, the best thing to do is just to start watching, give it until episode 5 or so, and see if you're hooked. If so, keep going in order.
That said, I like a challenge, so let's do this thing.
(Note: this article was written in 2012, after four seasons had aired.)
Key Episodes
The show just entered its fifth season as of this writing, so I'll be focusing on seasons 1-4. My goal here is to pick episodes that reveal important secrets or contain iconic scenes which will enable you to understand references. Note: I should probably note this for all of my entries, but if you haven't seen the show, the descriptions here might spoil you somewhat. I try to talk around the major plot points.
1.5 "5G": This is where the series really started to pick up for me, and it's really where the main plot starts. (If you haven't seen previous episodes, it will feel like you missed something. Don't worry, you didn't.) Don's tidily compartmentalized life is challenged when a man from his past comes into town. This is also get a good introduction to slimy Pete Campbell (Vincent Kartheiser) as he attempts to whore out his wife to one-up rival exec Ken (Aaron Staton)'s writing career. "5G" features what I believe to be the first truly captivating scene of the series (the final sequence), as well as the first legitimately entertaining one, in which Peggy (Elisabeth Moss) confides to Joan (Christina Hendricks) that she suspects Don is having an affair because he comes back to the office "all greasy and calm."
It is also acceptable to start with 1.4, in which we get our first look at the intricacies of Sterling Cooper office politics, but it's a little too heavy on the Pete Campbell for my tastes. In my experience, episodes 1.1 through 1.3 tend to dissuade new viewers; they're slow, sometimes heavy-handed, set-up-y mood pieces which are mostly only interesting after you are already a fan.
1.12 "Nixon vs. Kennedy": Against the backdrop of the nailbiter of a presidential race--which Don casts as "silver spoon" (Kennedy) vs. "self-made man" (Nixon)--Pete attempts to blackmail Don. Maintaing his cool on the outside, Don privately freaks out. In a powerful series of flashbacks, we learn the details that the season has been hinting at.
1.13 "The Wheel": If you've ever seen a Mad Men parody (such as the one they did on SNL), it's probably based on this episode, which contains Don's most inspired (and over-the-top) nostalgic ad pitch. In other news, Betty (January Jones) begins to suspect Don of cheating, Pete gets Trudy's (Alison Brie) father's business and HOLY SHIT PEGGY WHAT.
3.6 "Guy Walks Into An Advertising Agency": Sterling Cooper employees clash with the presumptuous Brits from the new parent company, leading to HOLY HELL WHAT THE CRAP.
3.13 "Shut the Door. Have A Seat.": In my favorite ever most exciting episode, the core team, assured the company is about to be sold, scrambles around trying to steal clients from a sinking ship so that they can start a new agency.
Bonus Episodes
Reiterating the caveat that if you like the show it will make more sense to watch them all in order, etc.
1.1 "Smoke Gets In Your Eyes": I'm not a big fan of the early episodes, which lean a little heavily on the "It's not like there's some magic machine that makes exact copies of things" factor, but the pilot is solid, and features some nice pulled-out-of-his-ass pitch magic from Don.
1.6 "Babylon": The A-plot for this one is reflections on the meaning of being Jewish, while in ongoing storyline news, Freddie (Joel Murray) discovers Peggy's knack for a turn of phrase during a focus group on lipstick, and she is offered copywriting work.
1.8 "The Hobo Code": This episode has everything. Don gets high with his bohemian girlfriend and flashes back to his not-so-glamorous past. Sal (Bryan Batt) is hit on by a man. Peggy's first copy is pitched, and Don sells it by pulling out bizarre nonsequiturs about kabuki and Jesus. Pete is insufferable.
2.2 "American Airlines": Pete's father dies in a car crash and he just keeps on sellin'.
2.4 "Three Sundays": Told in three Sundays: Sterling Cooper employees work overtime; Peggy resists the cute new pastor's imploring to confide in him; Don refuses to spank his son and confesses to Betty that he was abused as child.
2.8 "A Night to Remember": This is the episode where Joan (Christina Hendricks) briefly gets a fulfilling job.
2.12 "The Mountain King": Don, on a weird spiritual trip to California, visits a woman who knew him in his Secret Past. Meanwhile, back home, Joan's failure of a fiance is a terrible person.
2.13 "Meditations in an Emergency": Various people tell other people about babies they had, will have, are having, etc.
3.1 "Out of Town": Don and Sal bond on a business trip on which they both (try to) get laid. Back home, a British company is taking over Sterling Cooper, restructuring and forcing Pete and Ken (Aaron Staton) to compete for the same job, which Ken finds exhilarating and Pete predictably finds lemonsourbitchfacey.
3.9 "Wee Small Hours": Sal is fired for not taking one for the team when a major client hits on him.
3.11 "The Gypsy and the Hobo": Betty forces Don to tell her his secrets. Joan's failure of a husband joins the Army.
4.6 "Waldorf Stories": Peggy is upset when Don wins an award for her work. Don appears to be slipping when, drunk after the ceremony, pitches a lame idea he inadvertently stole. Peggy trades banter with the sexist new art guy.
4.7 "The Suitcase": Don and Peggy stay way late at the office, Don because he has nowhere else to go, Peggy because (though she complains) there's nowhere else she'd rather be. After elements of their personal lives blow up around them, they go to a diner together in one of the most genuinely friendly scenes in the show.
4.12 "Blowing Smoke": The new company's imminent failure leads Don to take some creative steps.
4.13 "Tomorrowland": Don brings his new secretary Megan (Jessica Pare) to Disneyland with him to help take care of his kids and while there, they WAIT I WASN'T EXPECTING THAT PART.
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