Sterling Cooparound: Celebrating the Supporting Characters of ‘Mad Men’


Don Draper gets enough virtual ink. Mad Men is his show. But it also belongs to the sprawling ensemble that surrounds him, because they’re the best cast of supporting characters on television. Let’s celebrate them, and some of the moments that make us love them so much, before we dive back in for the stretch run on Sunday night. Enjoy. And if we skipped one of your favorites, well, we’re sorry. We’ll make it up to you in Season 8.

Peggy Olson

Steven Hyden: Peggy Olson is my favorite. I’m not referring just to Mad Men or TV characters in general. I’m saying she’s my favorite, period. I care about Peggy. I feel I know her like she’s a real-life person. Obviously, this is a testament to the acting of Elisabeth Moss and to the show’s writers. But, honestly, I don’t care about those people nearly as much. Elisabeth Moss only looks like Peggy Olson. Elisabeth Moss didn’t rise from secretary to copy chief at SCDP while enduring one of the unluckiest love lives of the Love Generation. She didn’t soothe Don, con Roger, housebreak Stan, seduce Duck Phillips, or mentally destroy Ted Chaough. That’s all Peggy, though it’s not why I love her.

How do you sum up a person who’s been a part of your life for eight years? Picking one Peggy moment that stands out from the rest is impossible, because that’s not how you think about people you know. The people you know exist in your memory in a million tiny fragments, like this:

And this:

And this:

And this:

And definitely this:

Matthew Weiner, I respect that you don’t want to do a Peggy Olson spinoff. BUT SERIOUSLY, DO A PEGGY OLSON SPINOFF, WEINER.

Roger Sterling

Chris Ryan: Here are two clips of Roger Sterling paying people cash out of his pocket so that they will do what he tells them to do.

It’s been said that Roger Sterling is Mad Men’s comic relief, but I think it’s more that Roger knows that life is a joke. Whether he’s on LSD, drowning in vodka, on top of the world, bottoming out, on the outside looking in, or looking at Joan, Roger Sterling knows that life’s cruelty, its ups and downs, its highs and lows, are just setups and punch lines for some cosmic joke. In a show that’s so much about codes — hobo and otherwise — Roger has found a way of living that suits him. It’s not that he doesn’t get melancholy or ambitious. Daughters disappear, wives leave, lifelong loves remain out of touching distance, but somehow he seems comfortable. Money is just money. And there’s nothing that can’t be fixed by something else. Is this heartbreaking? I don’t know. He’s not without his passions.

He was an adman.

Joan Holloway

Molly Lambert: Joan Holloway taught me how to be a woman. When Mad Men started, I was about the same age as Peggy Olson (I still am), and like Peggy, I immediately looked to Joan as a model of what adult working womanhood was supposed to look like. It seemed to involve a lot of cute but uncomfortable clothes and high heels. And most important, a certain cool demeanor — a wry, slightly detached, seen-it-all attitude that I remember worshipping in cool female seniors in high school, and then again in college as a lowly freshman. Joan provides some really terrible advice on Peggy’s love life, but when she and Peggy are on good terms, she gives indispensably good advice about how to exist as a woman in the workplace without wanting to murder the world for being the way it is. It’s not always possible! I am now 31, the age Joan was in Season 2 when her driver’s license was hung on the office corkboard to humiliate her for being an unmarried secretary. I don’t know that I feel any more mature seven seasons of Mad Men later, but I’ve certainly nailed the detached, wry, seen-it-all attitude part. And from Joan I have learned a lot about how to maintain your dignity and keep it moving. 1 One of my favorite Joan moments was in Season 6, when she took her friend to the Electric Circus to get weird for the night. Joan’s life may not always be as glamorous (or even as barely tolerable) as she wishes, but she rolls with whatever is happening and sometimes even gets to be the goddess she certainly is. Thanks for everything, Joanie.

Pete Campbell

Juliet Litman: Mad Men is a show about anxiety — anxiety about changing times and keeping up, anxiety about moving on to subsequent phases of life, anxiety about having missed out, anxiety about having enough money, anxiety about being found out. The latter is the tension that motivated the early seasons of the show. In Season 1, this was a show about a man with a secret who was desperate to keep it as such. Enter Pete Campbell. Pete was Don’s primary antagonist in the early days — the irritating, bitch-faced accounts guy desperate to expose Don, even if he didn’t quite know what information he hoped to reveal. If you were on Team Draper, it was difficult to like Pete. He threatened to shake the foundational myth upon which we thought this show was built. Couple that threat with his odious treatment of Peggy and of his charming wife Trudy, and you have a bona fide villain. Season 1 Pete Campbell was not a good guy. He personified a narrow-minded archetype that is odious by 21st-century standards.

But just as time neutralizes many perceived threats, the evolution of the show nullified any harm that Pete could cause. And then he became fun. At the end of Season 2, Peggy finally reveals that she gave their child up for adoption, telling him, “I could have had you in my life forever if I wanted to.” It was a devastating moment, confirming Peggy’s imminent rise and Pete’s shattered view of himself. He never recovered from the revelation that a woman had affirmatively decided not to be connected to him. That moment in particular was not fun, but it wounded Pete in a way that has allowed Vincent Kartheiser to play him with some levity. Pete will never be the alpha at work and he will never be happy at home, and so all of his machinations and movements are subject to a black humor. His relationship with Beth Dawes ended in Sylvia Plath–esque sadness, but even that coupling had its moments of comedy. As evidenced by his liaison with the Californian real estate agent, Pete can’t have a proper affair without some high jinks — even when he’s single! I relish his quips in meetings, his directness with Don, and his everyday indignation over matters small and large.

Most of all, I can’t believe the conniving jerk from Season 1 commands any sympathy. But that’s the wonder of Mad Men. Even the villains are subject to the cruel progression of time. While we’ve watched Don and Roger stave off obsolescence over several seasons, it came to Pete early. He never fought it. He has dwelled in it, and it has been a joy to watch.

Betty Francis (née Draper)

Dan Fierman: When I had my first child, I turned to my grandmother. She was in her mid-eighties at the time, or just a touch older than Betty would be today. Her advice was as simple as it was useful: “It’s all bullshit. What the books say you should do now, they’ll say just the opposite in 20 years.”

That is worth remembering when considering Betty the Mother. She’s a horror, obviously. But she’s not a monster. She’s muddling through the best she can, a walking lesson on how there is no playbook to life, even for someone as privileged — in every conceivable way — as she is. If Mad Men is ultimately about the way that history moves inexorably forward and how the choice to stay left behind is a hugely destructive one, it’s hard not to view Betty as the most tragic figure in the series. She arrived on the show already an object of nostalgia. She seems likely to leave alone in a big empty house, surrounded by everything she thought she wanted and nothing she needs.

Also: Dude. That fat suit. Still not cool, Weiner.

Lane Pryce

Alex Pappademas: Each June 3, I wear a T-bone steak as a “big Texas belt buckle,” and no true fan of Mad Men will ever need ask why. I still miss Jared Harris’s flawless line readings, and I still miss Lane Pryce, who was never innocent, but had a capacity for shame, and was therefore as doomed as the ’67 Mets. He may have had Mad Men’s most legitimately tragic arc. He shows up in Season 3 to count beans on behalf of Sterling Cooper’s new British owners, but becomes the inside man who allows the new agency to come about by firing Roger, Bert, and Don. In return, they take him on as a partner, which means he gets to be the sole voice of reason at a fledgling firm otherwise composed entirely of irresponsible jerks (and one weird old guy who’s into Ayn Rand). On the plus side, Lane also gets to spend the next few years living a pretty respectable version of the mid-’60s American dream: He dates a Playboy Bunny, gets drunk at a Godzilla movie with Don Draper, and punches Pete Campbell in his stupid face. “I’ve been here 10 months,” Lane tells his wife, “and nobody’s ever asked me where I went to school.” Eventually, we found out why that climate of class mobility and self-reinvention appealed: The life Lane had left behind in England included a nightmare of a father who later showed up to beat him with a cane, as well as mounting debts.

This being Mad Men, he couldn’t fully escape from any of it. Lane casting off British restraint like a too-tight waistcoat and embracing groovy freedom like some transplant dandy around whom the mid-’60s Tom Wolfe might have spun 90,000 words of go-baby-go sociology would have been fun to watch, because Jared Harris is. But it would also have undercut everything this show has to say about work (seldom portrayed as a site for positive self-actualization) and America (doesn’t love you back). Lane makes an awkward pass at Joan Holloway, for whom he has pined; she rebuffs him so gently, it breaks your heart a little. Then, a few episodes later, he betrays her — when Pete suggests paying Joan to sleep with a client to help them land the Jaguar account, it’s Lane, thinking like a CFO, who suggests bribing her with a percentage of the company instead of cash. He needs them to get the business because he needs the money; he never gets it. I’m convinced that his death is more about Joan than it is about money — not for nothing does he try to do it behind the wheel of an E-Type first. And I’m convinced that if Season 7 leaves us looking back and thinking about where things began to fall apart for Sterling Cooper & Partners, Jaguar is where we’ll look. Lane may have died by hanging, but he was killed by a car.

Kenny Cosgrove

David Cho: I want to take a second and just give a shout-out to the winningest and nicest Mad Men character: Ken “Kenny” Cosgrove. I fully realize that a show full of Kens would probably be insanely boring and not unlike the USA television show Suits. I’ve never seen Suits but assume its premise is guys who are winners and wear suits, which is exactly what Ken Cosgrove is.

In case you don’t believe me, here is a small sampling of Ken’s greatness:

• Beat out Pete for the head-of-accounts job at the OG Sterling Cooper
• Got published in The Atlantic (the real magazine, lest you think it was the Atlantic Wire)
• Eventually married Alex Mack, on whom he then proceeds to not cheat
• Stood up to his bosses and won their respect when they asked him to leverage his wife and marriage for the company
• Wrote dope science fiction under the pen name “Ben Hargrove”
• Came up with the dope pen name “Ben Hargrove”
• Got to wear an eye patch
• Overall good dancer (see above)

Even Ken’s mistakes are big successes for the company! Don’t forget that as Putnam, Powell & Lowe was about to put in some handsome British dude to run Sterling Cooper, Ken brought in a John Deere that would later cut off the handsome British dude’s foot, leaving the company under the rule of Lane Pryce (R.I.P.). Without Ken, there would be no Chevy, no Sterling Cooper & Partners, and no crazy riches for everyone involved. YOU’RE WELCOME, GUYS.

Harry Crane

Dave Schilling: For every bribe, there must be a man or woman shameless enough to take it. For every Roger Sterling — immovable, unflappable, and perpetually confident — there’s a Harry Crane. Harry, oh Harry. The video Chris Ryan chose above, of Roger bribing Harry, is from “A Little Kiss,” the fifth-season premiere. What led up to the aforementioned transaction was Harry verbalizing his fantasy of passionate lovemaking with Megan Draper to Stan in the break room. In this scene, Harry shows off his command of French, which is notable because in my hypothetical, never-to-be-published self-help book, The Harry Crane Guide to Success in Business and the Bedroom, Rule No. 234 is “Learn a foreign language, then mangle it.”

Harry Crane is such a shameless pervert, such an untrustworthy weasel, that even Pete Campbell doesn’t have time for him. Don hates him. Jim Cutler hates him. Megan hates him. Look, everyone hates Harry Crane. Maybe his only friend in the entire seven seasons of Mad Men is Paul Kinsey, who, by the way, is also a complete asshole. Harry Crane is a complete garbage-mouth idiot, but besides Peggy, he’s also the character who has changed the most since the pilot. To be more specific, he’s gotten shittier. As he’s grown more awful, his clothes have gotten louder and more obnoxious to match his personality. Where once he dressed like a typical 1950s office drone, he subsequently morphed into some sort of Paul Lynde Hollywood huckster with an ascot for every occasion. Harry’s the type of guy who will fit right in in the 1980s — his white blazer sleeves rolled up to his elbows, with a vial of cocaine in his glove compartment. I pray that the final episode of Mad Men will see the Rise of Crane completed, allowing Harry to take his rightful place on the writing staff of Growing Pains.

Stan Rizzo

Holly Anderson: I could no sooner choose a favorite Stan moment than select a favorite star in the heavens, but this is up there. Look at him, taking knives in the arm with all the geniality of a toked-up St. Bernard.

It wasn’t as readily apparent back when he was the beardless, boorish thorn in Peggy’s walkin’ boot, but the hiring of Stan Rizzo was the onboarding of a much-needed audience surrogate for Mad Men. Stan is laughing at the dude quoting Tecumseh in a client meeting when nobody else feels he can. Stan is capable of telling Don how full of shit he is, at just the moment when we all want to climb through our television screens and do the same, and in the same manner you yourself would do (via a sick sandwich burn). Stan is the one person you can count on to always be telling everyone exactly what they need to hear, which is usually something like this. Stan, in the place where you stand. [Freeze frame, soothing jingle.]

Stan may be the only character in this contraption we can confidently say will go on to lead a rich, fulfilling life and die naked and smiling on a beach somewhere. That may be in like three weeks, or in 70 years. He’ll be fine either way. Stan everlasting.

Bob Benson

Mark Lisanti: It’s not often that Mad Men, a show that delights in frustrating the wilder expectations of its viewers, delivers exactly the resolution to a mystery that we were all hoping for. But by the time the end credits rolled on the 12th episode of Season 6, “The Quality of Mercy,” we had the answer to the Benson enigma we’d all craved: He was, in fact, the time-traveling bastard spy son of Peggy Olson, sent to keep an eye on the dealings of an up-and-coming ad agency. Incredible! The Internet had never been right about any television-related conspiracy theory before, and here it hit the suspicious nail right on its innocuously coiffed head, emboldening a new wave of subreddit sleuths to follow their every hypothesis to its inevitably correct conclusion. The Yellow King never saw ’em coming. Not great, Bob.

Just one episode prior, our then-still-inscrutable Mr. Benson tipped his hand in heartbreaking fashion to Pete, as you would be able to see more clearly in the above YouTube clip had some yahoo not curdled the impossible tension of the moment with a gag soundtrack cue. It still hurts to watch. Bob Benson. Beloit. Wharton. Sudden emotional exposure. Web of lies, about to quickly unravel. He’s brought two identities, just in case you forgot yours.

Glen Bishop

Katie Baker: “Why does everything turn out crappy?” a mustachioed Glen Bishop asks Don Draper in an elevator after a day of playing hooky in the big city with little Sally goes awry. “Everything you wanna do, everything you think’s gonna make you happy just turns to crap.” Don points out that Glen is too young to be saying such things, but that’s just it: In his young life, Glen has absorbed his parents’ divorce, been a bathroom voyeur and a petty vandal, caused a maternal meltdown thanks to a cherished lock of hair, and been shipped off to a fancy boarding school where older jerks pissed on his lax gear. When Glen talks about crappy, he knows whereof he speaks.

The word usually used to describe Glen isn’t crappy, though — it is creepy; there’s even a (terrible, spammy) Twitter account called @CreepyGlen. But it’s his bumbling beginnings that have made Glen both a fascinating character and an awfully believable one. Those opaque phone calls with Sally, those Holden Caulfield comparisons (the actor who plays Glen, Matthew Weiner’s son Marten, even has the middle name Holden), those half-assed games of Hockrosscer in the dorm hallways — such is the life of the misunderstood teen. But it’s often the misunderstood ones who ultimately come out on top.

Glen and Don’s elevator scene ends with Don asking Glen what he’d do if he could do anything; it transitions to the two of them in the car back to Hotchkiss, Glen smiling wide behind the wheel. Even the happy moments in the poor kid’s life are illegal. But later in the series, when Sally sneaks him and his handsy friend “Rolo” into a Miss Porter’s School bedroom, it’s no longer Glen who’s the creep. He’s the de facto grown-up, the guy who takes care of things, the dude you can trust with your worst. Those dickish older jocks who bullied him are the ones who will go off to college and be in for a rude awakening. Not Glen. You can’t crush a spirit that has already been broken, after all.

Filed Under: TV, Mad Men, Matthew Weiner, Jared Harris, James Wolk, January Jones, AMC, Jay Ferguson, Rich Sommer, Patrick Fischler, Martin Holden Weiner, Mark Moses, Christina Hendricks, Vincent Kartheiser, Aaron Staton