It’s stating the obvious to say that the point of Mad Men isn’t for viewers to like the characters — they all have their flaws, be they obvious (like one D. Draper) or more subtle (like pretty much everyone else). Still, there’s something infinitely affable about 1960s New York City’s foremost aging bon vivant and silver fox, Roger H. Sterling, Jr.
This, of course, is the whole point of Roger Sterling — his job is all about getting people to like him despite themselves. His ability to do it so effectively is what makes him such a killer account executive. He’s the consummate salesman, the smooth-talking, silver-tongued silver fox who charms women and media buyers alike. At the start of Mad Men, that’s all he is — he’s Don’s partner in crime (a status that’s rather undermined by making a pass at Don’s wife), and his most memorable contribution to Sterling Cooper is vomiting exuberantly after a long lunch that involves too many oysters and an ill-advised climb up the office stairs.
It’s not until his heart attack (one catalyzed by a threesome, let’s not forget) that we start to see Roger as more than a cardboard cutout. A brush with death reminds him of his own mortality, but it also makes him seem a whole lot more human to viewers. It’s a process that continues with the great unfolding of Mad Men‘s multi-season plot, as, just like everyone else, Roger accumulates ill-advised marriages and regrets and bottles of Smirnoff in roughly equal measures. He’s the sort of man you know you should dislike — he cheats on his wife, he’s a terrible father, he’s an unashamed capitalist with a penchant for casual racism. But you can’t, not really. Not completely. He’s too charming.
Roger’s greatest trick, though, is getting Roger Sterling to like himself. Despite himself. Because deep down, one suspects, it can’t be easy being Roger Sterling, Jr. He was born into his job, his destiny printed on the door of Sterling Cooper until such time as he came to claim it. It’s hard to imagine that not claiming it was never an option. In this respect, Roger is the anti-Don. If Don exemplifies the American dream of the self-made man, then Roger is the antithesis of that dream: he’s born with a silver spoon in his mouth, a man whose status is his birthright and whose success is never in doubt.
Indeed, the Roger/Don dynamic is one of the show’s most intriguing. It was Roger who discovered Don, back when the creative genius was selling fur coats for a living. Indeed, you might argue that it was Roger who created Don Draper, as much as Don created himself. Without Roger, there would have been no advertising, no awards, no mountains of cash. But at the same time, you might argue that it was Don who created Roger — it was Don’s genius that turned a small two-partner firm into a top 30 agency. And it was Don who talked Roger into going out on a limb to create Sterling Cooper Draper Pryce. The two of them need another, and it’s no accident that it was Roger who invited Don back into the fold and argued for his return.
Still, the message of that return is that things will never be like they were. There’s been too much damage done, too many bodies buried. The times are a-changing, both inside and outside the walls of Sterling Cooper and Partners, and it’s impossible to recreate the days of long lunches and unconstrained genius. No one can keep getting away with it forever. Except, maybe, Roger will.
It’s notable that of all Mad Men‘s lead characters, it’s Roger who most embraced the counterculture. The episode in Season 7 where he joins his daughter on a commune seems hilariously incongruous, and yet at the same time it’s also not surprising to see him sitting there peeling potatoes for the sake of a child he loves but never really knew how to raise. Similarly, his mind-expanding adventures on LSD, as well as being both endearing and hilarious, suggest an awareness of — or, at least a curiosity about — the fact that his work isn’t the be-all and end-all of his life.
This is a realization that’s been a long time coming to some of his contemporaries, if it’s come to them at all. It’s most likely come far too late to Don, whose decline appears inevitable and irrevocable. Roger, though, will probably continue as he’s always done — floating happily on the surface, drifting deftly out of the path of an oncoming storm the way that people will privilege always manage to do. You know you should probably hate him, and yet you can’t. He’s just too likable.