Top 10 Mad Men Season 1 Characters

Ranking the Top 10 Mad Men Season 1 Characters

Ever since the beginning, Mad Men was a show filled with rich characterization and fantastic performances. And even though everyone in the ensemble is a horrible person, we still love the Sterling Cooper gang no matter what. Here are the definitive Top 10 Mad Men Season 1 characters:

10. Joan Holloway

Joan Holloway is the most buxom TV character since Jessica Rabbit. Even though she starts the series as vain and arrogant, she’s the human embodiment of Mad Men‘s seductive style. Sure, Joan has terrible taste in men (Paul Kinsey, Roger Sterling, the ugly professor from “Long Weekend,” etc.), and sure, Joan is incredibly shallow and materialistic (when Peggy is being harassed by male co-workers, Joan’s advice is to “enjoy it while it lasts”), but at least Joan is true to herself. She’s just trying to make it in a man’s world, and if that means being the office bimbo will help her get ahead, then so be it. In her own way, she’s just as charismatic as Don Draper.

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9. Freddy Rumsen

Everyone loves alcoholic copywriters! Freddy is a breath of fresh air when compared to the sexist and misogynistic frat-boy antics of Pete Campbell, Harry Crane, and Ken Cosgrove. Even though he gets piss drunk at the office (season 2 spoiler) and is a little sexist himself (“old-fashioned,” is what we’ll call him for now), Freddy is one of Sterling Cooper’s most upstanding employees. He’s also the first to notice and foster Peggy Olson’s talent for copywriting, which lands her a job on the Belle Jolie account. Let’s raise a glass (Freddy’s recipe for a screwdriver: 5 parts vodka, 2 parts orange juice) to Mr. Rumsen, the most respectable worker in the office.

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8. Trudy Campbell

Despite only appearing in a few episodes, Trudy Campbell is the nicest, sweetest and most loving character in all of Mad Men. She’s a perfectly loyal wife. That’s why it’s so heartbreaking that she’s married to Pete Campbell, the biggest piece of shit in New York City (which places him high in the running for biggest pieces of shit worldwide). What’ll it take for them to get divorced? Well, she doesn’t leave him when he tries to pimp her out in order to get a short story published. And she’s not aware that he conceived a bastard child on the night before their wedding. Through it all, Trudy remains doe-eyed and faithful.

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7. Betty Draper

For the first eight episodes of the series, Betty Draper was the stereotypical TV housewife. Married to an adulterous husband, she has boring friends, boring hobbies, and goes to therapy. One day, Betty finally snaps — she kills a bunch of pigeons and instantly becomes one of Mad Men’s most interesting characters. After that, Betty’s tragic existence becomes much more relatable. The tragedy, of course, is that she’s entirely dependent on Don despite his numerous affairs. Her closest confidante is the weird, horny nine-year-old boy who lives down the street (which is a big reason why she doesn’t crack the Top 5, unfortunately).

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6. Peter Campbell

Pete Campbell is a sniveling WASP who expects everything to be handed to him. He craves approval at work and tries to blackmail his boss on more occasions than one. He consistently cheats on his wife and fathers a child out of wedlock. He came up with “direct marketing” — turns out it already existed — but he arrived at it independently. In short, Pete Campbell is the worst. But he’s also the character you love to hate. It helps that everyone else in the office hates him too. Luckily, Pete gets humiliated several times throughout the season, and each is more satisfying than the last.

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5. Rachel Menken

Menken’s department store comes to Sterling Cooper for a modern advertising makeover. Rachel Menken, the sexy Jewish heiress, falls in love with Don Draper’s old-school charisma. Likewise, Don is enamored by Rachel’s confidence and how she challenges his ideals. Soon enough, they begin a rapturous affair in which there are no secrets between them. But that means she eventually sees right through Don’s carefully crafted persona, and the romance ends abruptly and unceremoniously.

For Don, Rachel will forever be the one that got away. Ultimately, however, she was too good for him. He’ll spend the rest of the series trying to attain what he lost and spiraling deeper into existential crisis as a result. She was the most desirable woman on the series (other than Trudy Campbell, of course).

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4. Peggy Olson

Peggy starts at the bottom. In the first episode of the series, she begins a new job as Don’s secretary and then has sex with Pete Campbell. Although her on-again, off-again relationship with Pete is one of the more questionable decisions on the series, Peggy is by far the smartest and hardest-working employee at Sterling Cooper. By the season finale, she’s been promoted to junior copywriter (the first time since World War II that a woman has written copy at Sterling Cooper).

Peggy initially tried the Joan Holloway approach to climbing the corporate ladder, but she lacked the looks. Instead, she gets by on talent and diligence, which is how Don comes to be her business mentor. Peggy’s rise is one of the bright spots of Mad Men season 1, yet her unexpected pregnancy threatens to bring everything down at the end of the year.

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3. Roger Sterling

Roger Sterling is a smooth-talking ad man that loves to drink, smoke and sleep around — so basically a richer and older Don Draper. Unlike Don, however, Roger is (somewhat) at peace with who he is. He admits that “when a man gets to the point where his name is on the building, he can get an unnatural sense of entitlement.” However, he won’t readily admit that he’s old. That’s how he ends up puking in the office lobby after a 10-martini lunch, and how he ends up in the hospital after suffering a heart attack after having sex with a girl he picked up from the casting department.

Roger could easily be the main character of Mad Men, but then the series would lack its trademark introspection and have to just become a comedy instead. In fact, I’d love to see a TV show based around Roger’s antics. Even when he’s puking or almost dying, he’s always a fun time.

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2. Bertram Cooper

Simply put, Bert Cooper is badass. He’s the Madison Avenue version of Yoda, Gandalf and Dumbledore all wrapped into one— a wise old CEO that possesses infinite knowledge. Even though he doesn’t appear too often, he always makes the most of his screen time. A few Bert Cooper quotes that you should seriously consider getting tattooed on your arm:

• “New York City is a marvelous machine filled with a mesh of levers and gears and springs like a fine watch, wound tight, always ticking.”
• “Stop smoking so much, it’s a sign of weakness.”
• “Don’t waste your youth on age.”
• “The Japanese have a saying: a man is whatever room he is in.”
• “Mr. Campbell, who cares?”

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1. Donald Draper (a.k.a. Dick Whitman)

Women want him, and men want to be him (and vice versa). That’s because Don Draper’s appeal is universal. He’s not just an advertising executive; he’s a way of life. Even though he accidentally killed his sergeant in the Korean War, stole his identity by prying away the dog tag from his charred corpse, abandoned his family to start a new life, cheats on his beautiful wife every chance he gets and … well, I’m sure I’m forgetting some other major transgressions … but even though he does all these terrible things, he’s still the most magnetic, charismatic and downright interesting TV character of all time. Donald “Dick Whitman” Draper easily takes the top spot in these rankings — and it isn’t particularly close.

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