The 10 Saddest Things About Roger Sterling, Ranked

Though not always the most likable person, Mad Men's Roger Sterling is a complicated character, and he's endured no small amount of tragedy.

While Mad Men is often heralded as one of those "great TV dramas," it's also very, very funny. Most of the humor is derived from Roger Sterling, the namesake of Sterling Cooper (and later Sterling Cooper Draper Pryce). Roger is always quick with a witty retort, a scathing—but often hilarious—personal attack, or a snarky bit of condescension or sarcasm. In short, he doesn't tend to take things seriously, and it shows in his public demeanor.

But, most of that is for show. Inside, Roger is a horribly pained and borderline tragic figure filled with sympathetic issues.

10 His Horrible Health

It's hard to feel too sorry for Roger in regards to his physical health, as it is largely his own doing. His poor health is a major aspect of season one, as he suffers two heart attacks throughout the course of the season. This, despite being relatively young; John Slattery was 45 when the first season aired in 2007.

It's never explicitly mentioned, but Roger's poor health is largely attributed to his drinking and lazy lifestyle. The former proves particularly dangerous, as Roger is never without a hard drink in his hands.

9 Lingering Pain From The War

Roger's overt racism is one of his worst traits. In one case, he intentionally sabotages a business meeting with Honda simply because he doesn't like the Japanese. However, the show treats Roger's racism with a degree of complexity; he's not evil for the sake of being evil.

Roger, like millions of other men, had a horrible experience in World War II and brought home some nasty outlooks on life. One of them was a horrible view of the Japanese, whom he believes ruined his life and threatened the very existence of the United States.

8 Constantly Having To Entertain

Roger is a very entertaining man. Unfortunately, this aspect of his personality is often "pimped" by the company, much to the chagrin of Roger himself. Roger is the man who takes clients to dinner, the one who takes them to shows, and the one burdened with keeping them entertained and happy.

In many ways, he is the very face of Sterling Cooper. However, this does a number on Roger. He doesn't particularly enjoy entertaining, and the constant influx of alcohol eventually does a number on his health. In one instance, he even gives Lane Pryce advice on how to dilute his alcohol during a business dinner, something about which Roger obviously—and somewhat tragically—has a lot of knowledge.

7 Alcoholic

It's quite obvious that Roger is an alcoholic. While he never gets as sloppy as Don, Roger is certainly a lover of the drink. He drinks during business meetings, lunches, and dinners, he drinks at home, and he drinks whenever he enters Don's office—which is quite often.

While he may be more of a functioning alcoholic than Don, other characters still take notice. The worst part is that Roger takes pride in his drinking, telling Don, "my generation, we drink because it’s good. Because it feels better than unbuttoning your collar. Because we deserve it."

6 Always Wanting To Fit In

One of the saddest things about Roger is his constant attempts to fit in. Roger is a naturally charismatic man, so, luckily, fitting in never seems to be a problem. The issue at the heart of Roger's vulnerability is his unending loneliness, and, wishing to alleviate said loneliness, he often tries fitting in—both at work and on the wider cultural spectrum.

Despite being one of the oldest members at the firm, Roger is one of the first to embrace the counterculture. Does he do it because he genuinely enjoys it, or does he do it because that's what everyone else was doing?

5 Feelings Of Being Useless

Of a similar issue is Roger's buried feelings of inadequacy. Despite being the face and name of Sterling Cooper and SCDP, Sterling is constantly overshadowed by those around him. Don is the brains of the firm and often gets all the credit.

Pryce helped start the firm with his capital. Pete brings in all the business. Harry is forward-thinking with his devotion to the media. Peggy rises the corporate ladder to become Don's equal. Roger, meanwhile, is simply coasting on his name and inheritance, and it often leaves him feeling useless and unwanted at the firm.

4 Estranged From His Family

Despite being a charismatic and likable figure at work, Roger isn't particularly well-liked or respected by his immediate family. He and ex-wife Mona get along well enough, but it's clear that she sees him through a lens of pity. Sadder is Roger's complete detachment from his daughter, Margaret.

Margaret sees Roger as little more than an infinite wallet, and, even when Roger tries bonding with her through family heirlooms, she seems more interested in his money than his family history. She eventually abandons him altogether to live on a hippie commune.

3 Inability To Find Love

One of the most tragic traits about Roger is his complete inability to find love. His marriages to Mona and Jane don't work for various reasons, and the flimsy relationship he shares with Margaret eventually falls apart. One of the only people he feels a genuine connection with is Joan, but he's not allowed to have her. Luckily, Roger eventually finds love, peace, and contentment with Megan's mother—and Don's ex-mother-in-law—Marie Calvet.

2 Mortality

As one of the oldest members of the firm, Roger eventually faces the prospect of mortality, and it scares him. This is beautifully rendered in the sixth season premiere, titled "The Doorway." Roger learns that his mother has died, and, while he puts on an air of casual acceptance, it hurts him dearly.

The pain is further exacerbated when he learns that the building's shoe shiner has also passed away and left Roger a shoe shining kit, as he was the only person to inquire about his life. Perhaps seeing his own lonely self in the shoeshine man, Roger openly weeps over the prospect of death.

1 Utter Loneliness

Above all else, Roger is just an utterly lonely man. His relationships never seem to work, the woman he pines after remains at a distance—despite working in the same building—and his work doesn't offer any sense of happiness or feelings of accomplishment.

As such, Roger eventually turns to the counterculture and the sense of spiritual freedom that LSD provides. In one of season five's best scenes, Roger asks Marie "will you take LSD with me?" It speaks to numerous aspects of Roger's tragic character, and it is heartbreaking.

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