John's Favorite Shows #6: Mad Men

We’ve gotten a bit off-track, but I’m resuming our rundown of my favorite shows of all time by highlighting my ten favorite episodes of each.  If you’ve missed any of them, check out the links at the bottom of this post for all of the past roundups.

I did not purposefully take such a long gap between my favorite shows lists, but you’ll be forgiven if you don’t remember our last installment.

I will admit that at the moment I am the slightest bit sour on Mad Men, perhaps the best show currently on television.  The seventh season split was, most definitely, a bad idea.  I started watching this show during its second season (as I have pointed out before, it’s a rare day that I start watching a show in its first season, mostly due to my Pushing Daisies PTSD), but it was at the very beginning of the second season and what I love about the show is that it plays so well when you aren’t binge-watching it.  It paces perfectly with each week building to one giant revelation after another in the season finales, making you feel like you need to go back and watch every second once more.

And the show did a marvelous job this past season in the seven episodes that it gave us, finishing with two killer episodes before the mid-season break, but I do hate that they will have to risk all of that momentum as we head toward the finale.  Breaking Bad, in my opinion, has started an awful trend here that makes what is already a final few episodes to be savored feel more like a drag.  I hope that shows like The Walking Dead and Game of Thrones are paying attention-keep that giant, glorious final season together rather than spreading it apart.

Still, this is hardly the time nor place to complain about one of my all-time favorite shows, and so instead of dwelling on Matthew Weiner’s decisions, I’ll instead jump right into my favorite episodes.  Without further adieu…

10. “The Gypsy and the Hobo” (#3.11)

No one in the Mad Men universe commands more divided opinions than Betty Draper.  I sometimes wonder if it’s the fact that she’s playing a mundane, ordinary housewife (at least she is at the beginning of the series) or if it’s due to the actress behind the vacant stares (January Jones, who I maintain does a brilliant job in the series even though she has done nothing since in other performances to argue that she’s more than one-note).  Either way, the showdown was electric, with Don finally finding a conversation with Betty that he just couldn’t get his way out of, and that excellent ending, with Francine randomly asking “who are you supposed to be?” to Don.  After three seasons, Don’s world finally started to truly collapse, and January Jones got her finest hour on the show.

9. “The Beautiful Girls” (#4.9)

Mad Men as a title has always been a bit of a misnomer.  Really, this show’s most compelling characters have always been its women.  All of those women get to highlight this episode with wonderful abandon.  You have Peggy trying desperately to make a connection on a romantic level, failing miserably (Peggy is the quintessential failed work/life balance girl).  You have Joan, finally giving in to Roger’s pleas to rekindle their affair after both the betrayal of her husband rejoining the army and a mugging.  And of course you have poor, poor Sally, pushed to spend time with her father’s mistress and then, even worse, her gorgon of a mother (Betty was ruthless after that divorce).  This is a wonderful showcase for all of them, and proof that Mad Men can totally dominate, even if it’s not the midseason high or the finale.

8. “Nixon vs. Kennedy” (#1.12)

On a night of a deeply divided election (all season long we’ve been hearing about how Sterling Cooper is desperate to elect Richard Nixon, but we all know that that’s eight years from happening), we get to learn a whole lot more about Robert Morse’s enigmatic Bert Cooper.  I could focus this episode on the antics in the office (oh how some of these men have changed dramatically as this series has worn on, particularly Ken) or everyone goofing around over Paul’s script.  But really, this episode is on this list because of the showdown between Don and Pete, a longtime coming in this episode, as Pete tells Bert all about Don’s real-life as Dick Whitman (doesn’t that story seem eons ago at this point?), and Bert replies with, “this country was built and run by men with worse stores than whatever you’ve imagined here.”  It’s a telling moment for the man behind the curtain, and a sigh of relief for Don.

7. “Meditations in an Emergency” (#2.13)

Set in the backdrop of the Cuban Missile Crisis, we have two major stories continuing in the series.  The Draper marriage, never on particularly solid ground, gets thrown a sharp curve when Betty finds out that she’s pregnant.  She decides to stick it out with Don after he apologizes once again, and this is the last such reconciliation for the two, unless you count that quickie on the field trip a few seasons later.  On the flip side is a rough separation for Pete and Peggy, who may have been the love of his life but he didn’t see it at the time.  He admits that she’s the one, and then she, in the most direct, matter-of-fact, and desperate way possible, tells him that she had his baby, and that she gave it away.  Pete, so desperate for a son, had one, and will never get to know him.  Part of the genius of this series is that the son never returned and Pete never had one to make up for this emptiness (he said, hoping he’s right for the final episodes of the series)-this was our only moment of closure with one of the most important aspects of the first season.  Life moves on, and Pete and Peggy would never again be together.  And we continue to be shocked by how much it never happened.

6. “Waterloo” (#7.7)

Sometimes you get an episode that gives you something you’ve been desperate for the entire run of a series.  Ross and Rachel finally getting together, for example, or perhaps some sort of retribution for John Locke.  You need it, and after a rough few seasons, it was about damn time that something good happened to the people at the firm, with McCann Erickson offering to buy shares of the company, making all of the partners (Joan, Roger, Don, and the like) all wealthy beyond their dreams.  You also got some whimsy and hope in the episode, like Peggy’s successful play with Burger Chef and Roger gleefully pushing Harry out of the meeting, keeping the scummy Mr. Crane out of the lucrative deal.  Best of all was a wonderful sendoff of Robert Morse, singing “The Best Things in Life are Free” as we bid adieu to his character with the moon landing.  A blissful calm before the end.

5. “The Wheel” (#1.13)

The first season of the show was more mysterious, more plot-and-less character based.  We had Don hiding his affairs and his secret identity.  You had Peggy hiding her pregnancy and desperately trying to find her place in a man’s world.  And you also had Betty, confused about her role in adulthood, having those creepy conversations with Glen and wondering what to do with her failed marriage.  All of these come to a head in this episode, with Betty trying to find solace in her therapy, Peggy giving birth, and Don watching as his most lasting connection to Dick Whitman, his brother Adam, kills himself.  It’s a series of major moments, but all of them feel very earned-there was no rush here, and though none of these moments would seem as strong years later, they started a great train toward whom these characters would eventually become.

4. “The Strategy” (#7.6)

Don-and-Peggy episodes are the crème de la crème of the series, and even the most casual of fans get giddy when they come about.  Don and Peggy bouncing ideas off of each other, both of them questioning their lives over the course of the entire series is such a Mad Men genius moment.  Other shows tie together loose ends and focus on getting as much good as possible, but Mad Men is very much about the bitter, and is smart enough to know that these people have made serious, life-altering mistakes (much like we all do), and it’s deeply fulfilling to hear them discuss this.  The entire episode is a roller coast of excitement, though, from Joan getting a “marriage of convenience” proposal from Bob and Roger finally realizing a way that he can matter in his firm (and outmaneuver Harry and Jim), but nothing quite beats Don and Peggy (and Pete), eating in a Burger Chef, enjoying the spoils of their work.

3. “The Other Woman” (#5.11)

During the late aughts, when I would put together my lists of favorite TV shows of the year, Lost and Mad Men consistently were pitted against each other, and so I’ve long thought it funny that they coincidentally both have an episode entitled “The Other Woman.”  With all due respect to Juliet Burke, who was in the center of Lost’s episode, this is a considerably stronger installment in a series.  It also features one of the great moments of Christina Hendricks’ career (if she wasn’t going to win the Emmy that year…), as the entire firm tries desperately to land Jaguar, and we get perhaps the twistiest moments in the history of Mad Men (Weiner strives harshly for realism and no-spoilers in his series, an attitude I applaud, but rarely does he give the audience something that seems like a switcheroo).  The pinnacle of the episode is Don, trying to save perhaps his best true friend on the show, Joan (Peggy, let’s be honest, is more of a proxy daughter), from sleeping with Herb Rennet to land the account.  He arrives too late, and Joan becomes a partner in the firm, but at a terrible and degrading price.

If that weren’t enough, you get the final moments of the episode, with Peggy finally admitting that she’s had enough and is going to work for Ted.  In a deeply affecting scene, you have Don being at first dismissive of Peggy quitting, and then realizing that he’s lost her, not taking her hand to shake it but to kiss it.  Elisabeth Moss’s “don’t be a stranger” was a heart-breaking cap to a season-long fight.

2. “Shut the Door. Have a Seat.” (#3.13)

My favorite moment in this landmark, pinnacle episode is Don stating, “Joan, what a good idea.”  It’s the most matter-of-fact line in a series that finds so much in silence, and it was also the moment I remember watching (live) and thinking “yes, Joan-that’s everyone!”  This entire episode, though, after a season where so much suffering occurred at Sterling Cooper, was a wonderful splash of water for a show that could have risked becoming stale if it started to repeat itself, which it looked like it was about to do.  Instead, we had the entire gang quitting in the face of the McCann deal, and in an Ocean’s Eleven style heist, steal office supplies and clients away.  We also saw the dissolution of Betty Draper’s marriage to Don, as she jets off with Henry to get a divorce in Reno.  All-in-all, we were just as excited as Don when he showed up at his new apartment, suitcase in hand.  This was the start of something new.

1. “The Suitcase” (#4.7)

In the giant pantheon of Mad Men episodes, you’d be hard-pressed to find one more universally adored than “The Suitcase,” which comes as close as the series could to being a bottle episode (it focuses almost entirely on Peggy and Don, or people reflected in their eyes).  The result is mesmerizing and fascinating acting from both Elisabeth Moss and Jon Hamm, each feeling around two highly introverted characters.  We see them argue, air their dirty laundry, and weep over the failures of their relationships and their dreams.  We left this episode, almost exactly in the middle of the show, knowing much more about both of these haunted individuals, and would continually find ourselves coming back to the Suitcase, remembering how much an opened door can change your life.

And those are my favorite Mad Men episodes-there’s certainly a plethora of additional episodes to choose from-which are your favorites?  Who would you put at number one?  Share in the comments!

For more of my favorites: Girls, Pushing Daisies, How I Met Your Mother, Game of Thrones, The Office, Ally McBeal, Sex and the City, Desperate Housewives, South Park