Mad Men is one of those shows where everybody gets a killer line from time to time. It’s a series about people who are quick-witted, and their ability to read a room is how they turn a failed ad pitch into gold. Only one character has proven time and again an inability to read the room, and a profound skill for making those around him feel instantly sick and tired of him. That is none other than Vincent Kartheiser’s Pete Campbell.

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When the show begins, Pete starts as a smarmy accounts executive who can’t shut up to save his life, a main antagonist of sorts to Don and the rest of the Mad Men gang, second only to cigarettes. As the seasons go on, Pete is slowly turned into a walking punchline.

10 Unwelcome Comments

From the moment we are introduced to Pete, we already know what everyone at the Sterling Cooper Advertising Agency thinks about him. Don, introducing Pete to his new secretary, Peggy, shows us everything we need to know about the guy. Pete wastes no time in offering unsolicited comments about Peggy’s body, and she makes it clear that his comments are unwelcome.

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Pete doubles down, saying, “If you pull your waist in a little bit you might look like a woman.” This moment serves as an appetizer for the many Pete-isms yet to come. Don apologizes, saying, “Sorry about Mr. Campbell here, he left his manners back at the fraternity house.”

9 None of His Business

At the office one evening, a package arrives for Don Draper. It’s from his long-lost brother, who wanted to convince Don to welcome him back into his life. Accidentally having the package dropped into his lap, Pete takes it home and rifles through the materials, learning that Don is not who he claims to be. Ever the opportunist, Pete tries to advance his position at Sterling Cooper by blackmailing Don. The plan backfires spectacularly, as Bertram Cooper, one-half of Sterling Cooper, couldn’t care less about the situation.

8 Pete The Writer

When Pete finds out that his friend and coworker Kenneth Cosgrove has had a story published in The Atlantic, it instills the idea that he too should be published. After all, why should anyone else have anything nice to call their own? Knowing that his wife Trudy has a connection with The New Yorker, an old friend named Charlie Fiddich, he proceeds to put her in a bad position. Sure, Charlie will publish the story, but Trudy has to be willing to have an affair. When Trudy rebuffs Charlie’s advances, Pete’s story is thrown to Boy’s Life, a major blow to his ego. When Trudy tells Pete about what happened, he scolds her for keeping him from greatness.

7 Chip ‘N Dip (They Got Two)

As a wedding gift, Pete and Trudy receive a “chip and dip” (they got two) from one of Trudy’s extended families. Knowing that they can use the money for their newlywed expenses, Trudy sends Pete to the department store to return it for the list value of $22. Meeting the clerk, Pete tries to put the moves on her, to which she is none too charmed to be receiving his attention. Having failed to impress her, Pete presses harder for the refund but is told that the best that they can do is to give him a store credit. Pete accepts and promptly buys a gun for the same price. Trudy is understandably furious at the impulse decision.

6 Starting a Family

At least one of the Campbells is eager to start a family. Trudy brings Pete to the doctor to test the viability of his sperm. Pete, reticent, to say the least, goes along with her plan. When he finds out that his men can “leap tall buildings in a single bound,” he turns to Trudy and says that the problem is her.

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Pete, not one for knowing how to console, then tells Trudy to go see a doctor and allow him to do whatever it is that he does. The scene is all-time awkward moment that shows just how out of touch Pete can be.

5 Poor Freddy

When Freddy Rumsen is a little too drunk one day at Sterling Cooper – a place where that sort of behavior is usually a good thing – he ends up urinating on himself. The rumor spreads like wildfire through the office and ends with Freddy being swiftly dealt with. When Peggy finds out that Freddy has been put on an open-ended six-month leave, she traces the story’s leak to Pete, who told Roger about it. When Don finds the men standing around doing impressions of Freddy, he scolds them, saying, “Sure, it’s just a man’s name.” Pete got to share his story, but at what cost?

4 The Easy Life

On the night of his bachelor party, Pete sleeps with Peggy. the two of them have an incredibly brief and uncomfortable affair, and then Pete does everything he can to alienate her. Throughout the rest of the first season, we see Peggy go through her private pain as she experiences this unwanted pregnancy. After she’s given birth, we see that the baby is being cared for by her mother and sister in their shared home. One day in the office, Pete talks about how hard it is being him, saying to Peggy, “You have it so easy.” It takes everything in Peggy’s power not to tell him about the child.

3 All Aboard

Pete begins an affair with Beth, the wife of Howard Dawes. When Beth is hospitalized for depression, Pete visits her and tries to sway her from her forthcoming electric shock therapy. Later, on the train, Pete bumps into Howard and the two get into a row. When Howard realizes the extent of Pete’s feelings for his wife, the argument becomes a full-blown fistfight. The train conductor tries to intervene and restore peace, but Pete is quick to turn his anger on the kindly conductor. Needless to say, Pete ends up being punched in the face and is thrown off of the train.

2 More Blackmail

During one of his many excursions to a brothel, Pete ends up bumping into his father-in-law, Tom Vogel. The two stare at each other briefly, exchanging an awkward hello. That seems to be the end of it, but Pete’s gears are already fast at work. When Freddy returns to the office, he brings Ponds Cold Cream along with him and wants Pete as far away from him as possible, which is understandable given how their relationship ended.

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Ponds has another condition: give up Clearasil. Pete holds the brothel encounter over his father-in-law, who brought Clearasil to the ad agency and makes him switch it out for Vicks Chemical. Of course, if Tom didn’t give Pete what he wanted, who knows how Pete would have paid him back.

1 Another Fistfight

When Pete and the gang take the head of Jaguar Cars, Edwin Baker, out for a night on the town, they decide to head to a brothel. There, Edwin proceeds to cheat on his wife, as do the other men except Don, who does that sort of thing elsewhere. When Edwin’s wife finds out, it costs the ad men the account. Lane Pryce, who more or less coordinated the entire deal, confronts Pete in the boardroom. Pete then throws a slur at Lane and the two of them decide to have it out in a fight. There’s a charming moment when we see the shocked reactions of Don and Roger as they see Pete sulk off to clean his bloodied nose. He had it coming.

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