As part of their ongoing analysis of the well-defined, flawed characters of Mad Men, Debra Minoff and Susannah McCullough of ScreenPrism take a look at the stalled, privileged existence of Roger Sterling. At the beginning of the series, Roger is the ultimate playboy with the world at his feet. Yet as the years pass into the 1960s, Roger’s small-mindedness, sense of entitlement and inability to let go of the past ultimately left him stuck in the same place, while others who had to work for their success moved onward and even past him. It was only when he put away these childish things, that he allowed himself to finally be loved.
It’s symbolic that Roger’s endpoint is a lot less grand than Don’s, yet it’s satisfying perhaps because of its smallness Roger needs to stop teasing youth or some grand important purpose and focus instead on the simple human satisfaction of feeling love. …It’s easy to envy Rogers lifestyle but in the end we see that we might be better off for not having all that he has.