7 Seasons In, Roger Sterling Has Become the Hero of ‘Mad Men’

by Kolby Solinsky

Editor, White Cover Magazine

LINE - White Cover Magazine

I watched last week’s episode of Mad Men – the third of this seventh season, titled “Field Trip” – three times. I watched it when it aired, on Sunday. I had recorded it, so I watched it again on Monday. And then again, on Tuesday.

I couldn’t get enough. The redemption of Don Draper was glorious. Even when his colleagues were putting him through the ringer, he undid every bit of cruelty being thrown at him with a calm and poised “Okay”. Seeing Joan and Peggy and Bert now turned on the man who at once did so much for them, even if they fail to see it now, was delightful… because you knew they were about to get the last thing they wanted, a Draper facial, even if their lifeless eyes and toothy smiles lied to us as if to say, “Don’t worry. Rome is fine without Caesar.” Seeing the born-a-dinosauer Lew Avery knocked down a peg or two was perfect, as well. Lew is the caricature of every boss you’ve ever hated trying to excel under, the guy who tells you you’re working too hard and the job should take you longer but who then chides you for thinking about crossing the road before you do, all because he’s worried about how he can account for it as a part of your paid time.

And all of that was a main course to a perfect dessert, the sign-off song “If 6 Was 9” by Jimi Hendrix. It wasn’t unlike the ending scene of Season 4, Episode 1 with “Tobacco Road” by Nashville Teens – you had Don Draper finding himself after 60 minutes of internal confusion and external torture, and you had a violently strummed rock song serving as the mic drop once he did.

But after those three long-winded, self-indulgent paragraphs and this sentence, I haven’t even mentioned the real reason I loved that episode so much… Roger Sterling.

And last night’s entry – “The Monolith” – had the silver cougar pouncing once again.

Everyone around Roger Sterling is falling apart and has been for years. when Mad Men started – with “Smoke Gets In your Eyes” – we thought he would be the first to fall, but he hasn’t. He’s still eating his food while everyone else is passed out on the couch.

The latest casualty is his daughter Margaretand how did it take us male viewers so long to realize just how hot she was? – who joined some sort of religious cult in inner-state New York, as her mother Mona calls it. Margaret and her husband call it a commune. Either way, it’s pretty Manson-like, and it’s the exact sort of place you imagine when you think of the 60’s if you didn’t actually live through it – a decade when a few lost their way and vanished into a counter-culture that was stroked and yet rejected by the male-dominated, one-vision world they grew up in during the 50’s and 40’s.

Guys like Roger are ironically the reason Margaret’s commune and places like it exist… Roger smokes the dope, bangs the women, and swims in their California pools, but his age and his suits date him to a time 20 years prior, when men were men and everyone else fell in line.

Roger’s last words to his daughter – the “I’m sorry but you don’t get to do that” way he addressed her abandoning her son and her husband – are typical of how every older generation looks at the younger one, but in this case it’s founded in something very personal, as is everything Roger does.

Roger fought World War II, as you know if you’ve watched a second of the show. He paid his dues while others paid with their lives, and he gloriously came out of 1945 into a post-War America fueled by a desire to get it right from that point on. But they also had a belief, many of them, that they either owed something to the guys who didn’t make it home. When they poured one out for their homies, they actually had homies down there waiting for a sip. The rest of us? We should be privileged to not have that experience, but we shouldn’t fake it either, and Margaret does.

And, coming out of the War, we’ve learned that Roger had the money and the opportunity – his father founded Sterling Cooper with Bert and Roger hopped on the gravy train – to make it. But he also had the skill and he had the charm.

Roger is likeable in so many ways, his personality being the only reason any of them matter. While it’s easy to label someone like him a Trust Fund Baby, Roger has atoned for it with the way he views everything – and everyone – around him.

Could you really care if he was handed everything on a silver platter? It would go with his hair, anyway.

I’ve heard him called cruel and amoral. He’s not… conflicted and flawed, certainly. But who isn’t flawed?

He’s a chameleon, the guy who could somehow square the circle in his head and co-exist as the kind of person who once tried to torpedo a massive new deal with Honda just because they were Japanese (remember I mentioned he fought in World War II) but then also hopped on the LSD train, started wearing ascots, and (by the beginning of Season 7) is living a Free Love swinger’s lifestyle.

The first time we see him in 1969, he’s waking up in a dark apartment, just post-orgy. He then goes to bed at the end of that episode – titled “Time Zones” – with his new girl, who’s fondling another man on the other side of her.

This is a Roger Sterling who – at the beginning of Mad Men, dated to 1960 – was lying to himself about everything, from the dangers of cigarettes to a heart attack that very realistically could have wiped him out.

When we say “Rich White Male”… we’re talking about men like Roger Sterling, at least the one in 1960.

Remember that bit in Season 1, when Roger tried to hit on Don’s then-wife Betty? That was all because a couple cute women looked at Don in a bar and not at him. He was insanely jealous, permanently desperate to be a Draper.

It was that desperation that led to him divorcing his early wife Mona for the under-25 office-oggled Jane Sterling, and then he left her because, well, he was over it.

But now it’s all in the past and he and his ex-wife, Mona, get along better than almost every other married couple in the show. Their meetings don’t seem to be lined with tension, but actually a bit of sexuality and admiration.

“You’re a lioness,” he tells her at Margaret’s wedding in Season 3, the day after the Kennedy assassination. “Thank you for ignoring the urge to eat your cub.”

Everything Roger does is, surprisingly, driven by a sense of loyalty – and it’s so strong he seems to shock himself with it.

You could forgive the way he screwed around on his wives Jane and Mona because you knew he was actually madly in love with Joan, and he still is.

That bit humanizes the guy. It shows you he’s got a heart somewhere, and there’s really only one woman who’d drop anything – and any other woman – for. He just met her too late.

And in “Field Trip”, his loyalty to Don wasn’t just affirmed but it was signed in blood.

The at-first-glance flaky Roger told him to come back and then shoehorned him through the rest of his partners, Joan and Bert and whoever Harry Hamlin plays.

From Don’s point of view, Roger had carelessly told him to come to the office, failed to tell anyone else about it, arrived lated and drunk, and then just sort of winged it from there.

But from the viewer’s seat, you saw him brilliantly and vigorously campaign for Don – calling him a “genius” while he yelled at the top of his lungs, threatening the roundtable with the realization that, if Don didn’t return to Sterling Cooper, he’d most certainly be stealing clients from them from someone else’s business card very soon.

Roger has always been jealous of Don. He’s been upset with him, too – the on-occasion best friends barely made up by the end of Season 3, with Don pushing Roger to the curb after he left Mona for Jane – but it’s clear now how much Roger admires him.

And he admires his daughter, sorta, as well. And he admires his ex-wife. And Bert, too.

He’s gone easy on Peggy and mentored Pete, even though he was coaxing along the guy who wanted to replace everyone, Roger included. He humiliates Harry Crane with every chance he gets, but only behind his back. (I seriously think that’s a best case scenario, in Harry Crane’s case.)

Roger Sterling started out as the wise-cracking, old-but-he-doesn’t-know-it, grey-haired anti-hero of Mad Men. But, a decade into the show and with everything he knows – his family, his friends, and his country – awkwardly transitioning from prosperity to perhaps disaster, he’s still standing beside and above everything.

He’s the show’s version of the idea that you want to be the guy attending the party and supplying booze to the party and MC’ing the party, but you never want to be the one hosting the party. Make a profit, but don’t be responsible for the mess. And have fun doing it.

Roger Sterling isn’t an anti-hero anymore. He’s just a hero.