By Blake Baxter (@bbax2)
For five seasons, we, the obsessive viewers of Mad Men, saw the sometimes inscrutable, but always fascinating New York ad man Don Draper go through his share of highs and lows. In the early seasons — back in the early 1960’s — it seemed like despite his checkered past and myriad flaws, Don Draper pretty much always ended up on top. However, as the decade progressed, we began to see that Don’s talents and charms could only take him so far. Sure, they enabled him to attain an assortment of professional accolades and allowed him to effortlessly get into the pants of any woman of his choosing, but they couldn’t save him from his own damaging, selfish impulses; selfish impulses that continuously isolated him from everyone who once was, or could have ever been meaningful in his life.
In season six, we saw Don, as well as almost everyone around him save ex-wife Betty, struggle by making the same mistakes they’ve made in the past, only in different circumstances, in a much different time. The year 1968 was Don’s true nadir. Season six was the darkest of Mad Men‘s run thus far, and that is saying something for a show whose fifth season was essentially about how empty life can be, even at times when you have everything you ever wanted — be careful what you wish for, indeed! But among the doom and gloom was one effervescent (though artificial) ray of light in the form of Sterling Cooper Draper Pryce newcomer Bob Benson.
Okay, Bob may not have always been the most well-liked person in the office and and viewers may not have really ever known entirely what to make of him, or his intentions, but you have to appreciate everything he brought to the table over the course of the season. When we first met Bob, he appeared to be nothing more than your standard, brown-nosed ladder climber. In fact, even the generally good-natured Ken Cosgrove dismissed him as such and forcefully put him in his place. Many people who watched the show also dismissed him, writing him off as just a new face in a growing workplace that now extended to two different floors — no more significant than Danny Siegel. But Bob just kept popping up, consistently lighting up the screen — sometimes only for seconds at a time, in the background, bugging familiar faces. He constantly had a beaming smile on his handsome face and was always offering to help anyone and everyone. His coworkers, however, oftentimes neither wanted his help nor appreciated his uncanny kindness. Nevertheless, Bob never failed to be the most kind and persistent person in a sea of miserable bastards.
But after a while, cynicism began to creep in and viewers started to question his intentions. Could someone really be that genuinely nice in a place almost entirely void of human decency? Need coffee? Don’t worry, I always carry two. Visiting a whore house? I’ll take the bill. You’re sick? I’ll take you to the hospital and take care of you. Whatever you need. Something had to be up. Just what is this supposedly altruistic Bob Benson character really up to? Is he up to anything at all? Is he doing all this just to advance his career, or is there an ulterior motive?
Everyone had different moments of suspicion. Some thought the red flag was when Bob went out of his way to help Joan Harris because she is, after all, a partner and one the most powerful people in the agency. He’s just trying to get on her good side, or worse: win her affection for his own personal gain! Conversely, others hypothesized that series show runner Matthew Weiner’s intention was to make Bob Joan’s love interest all along. It wasn’t clear that something was truly amiss until he had a suspicious exchange with the perpetually troubled Pete Campbell. Pete’s brother hands off their hectoring, dementia-suffering mother to Pete to take care of, but Pete is already in over his head at work. Luckily for him, Bob generously offers the services of a live-in nurse named Manolo whom he knows because he nursed his father back to health. That’s all well and good, but if you have a good memory and listen closely, you will realize that Bob told Ken that his parents were dead at the beginning of the season. What is Bob Benson hiding?
At this point, the Bob Benson intrigue magnified from a minor mystery to a fever pitch. Is Bob Benson a journalist? Could he be a spy? Is he a sociopath? Could he be a liar and a good person, still? Boy, he sure likes Pete a lot. Could he be a homosexual?
More than ever, fans wanted to know what Bob Benson was all about. And, not only was he among the most compelling figures in an ensemble of television’s most fascinating characters, but he was also responsible for some of the most funny moments of the season. Bob’s ubiquitous presence resulted in multiple hilarious outbursts from various characters. When he intruded on an argument between Michael Ginsberg and Jim Cutler, Cutler screams “WHY ARE YOU ALWAYS DOWN HERE? GO BACK UPSTAIRS!” In the finale, when he cordially asks Pete how he’s doing: “NOT GREAT, BOB,” Pete angrily, albeit humorously replies. But though he gets under his colleagues’ and bosses’ skin, he leaves an impression. Bob increasingly makes appearances at meetings and pitches as the year progresses. By the end of the season, it isn’t surprising that he’s working on the biggest account in the whole agency, it’s logical.
Bob Benson seems to be making all the right moves until things go sour with his adored superior, Pete Campbell. Pete has suspicions that his demented mother has either fallen for Manolo, or that he is taking advantage of her in her fragile state. Bob Benson, however, asserts that Manolo has no such designs for his mother because he is a homosexual and then, with a passionate monologue and the slightest graze of the thigh, suggests that he might be one, too. Pete, repulsed, walks out in disgust, intending to destroy Bob Benson’s once-promising career. But when he starts digging into his past, he discovers, to his shock and horror, that Bob Benson isn’t who he says he is. In fact, Bob is just another ambitious chameleon, aspiring to acquire prominence and escape his impoverished roots like another alliteratively-initialed charmer that he knows all too well. And so, Pete changes his game plan. Instead of taking down Bob, he flaunts his newfound knowledge of the charlatan right in front of his face. For once, here, we see Bob drop the Mr. Nice Guy act and show and display a moving mixture of despair and disdain before Pete reveals that he isn’t going to expose him, because he’s learned that guys like him get to do as they please and he won’t be able to stop him. At least this time, though, he’ll have leverage when he works alongside him – or so he thinks.
In the season finale, Bob Benson gets the last laugh against Pete when the two of them are in Detroit working on the Chevy account. Pete jokes and flatters the car manufacturers because Pete does his homework and can schmooze with the best of them, but Bob has been paying attention and knows that Pete can barely drive. And so, like a spurned lover, Bob tauntingly coaxes Pete into test driving the luxurious 1968 Camaro, knowing that he’s doomed to crash it and cause as much damage to his career as he does to the car. Perhaps that’s what he wanted all along. But it’s also possible he didn’t mean any ill will towards anyone until Pete hurt his feelings. There’s also the disturbing news of Pete’s mother who has apparently run off and married Manolo before tragically falling off a cruise ship. Pete thinks Manolo is responsible, but can’t help but blame Bob, too. There are just so many variables.
Pete’s discovery revealed that Bob’s origins weren’t consistent with who he said he was, but Bob’s actions afterwards proved we still have a lot to learn about a man surrounded by mystery for much of season six. I, for one, can’t wait to find out more about one of the few bright spots of a season shrouded in darkness.
Blake Baxter is a native of Illinois and a 2013 graduate of Eureka College. He currently covers the Carolina Panthers for Football.com and previously covered college basketball for ESPN Louisville during the 2012-13 season. He has also written about sports, pop culture and politics for The College Fix, The Wine and Cheese Crowd and an assortment of newspapers. Blake works in the communication and marketing field for Technical Solutions & Services, but aspires to write full-time someday.