Mad Men: The 10 Most Darkly Hilarious Scenes, Ranked

Mad Men is one of the all time greatest TV dramas. But some may forget just how funny the show could be. Mad Men often veered into comedy, and one could certainly make an argument that the show was more comedy-drama than straight drama. The characters had funny lines, there were some fantastic sight gags, and even a little bit of slapstick.

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That said, a lot of the show’s humor is based in dark comedy. Some fans don’t know whether to laugh or be shocked and appalled, but therein lies the genius of the show’s writing and directing.

10 The Lawnmower Accident

The lawnmower accident is perhaps the quintessential example of dark humor. Not just in Mad Men, but in general. When the British arrive at Sterling Cooper, Lois accidentally runs over the foot of Lane’s replacement with a riding lawnmower.

It shreds the man’s foot and sends blood splattering onto the windows and various nearby characters. It’s so shocking that it turns hilarious, especially when it comes to some of the later one-liners like “He’ll never play golf again!” and “Just when he got it in the door.”

9 Lane’s Jaguar

Lane's attempted suicide

After characters spoke about the unreliability of Jaguar cars all season, season five pays off the numerous discussions in the most brutal and darkly hilarious way possible. Lane Pryce attempts to suffocate himself in his new Jaguar car – only, the car won’t start.

Cue Lane pathetically holding on to a piece of his broken glasses while trying to fix the engine. Meanwhile, his car is simply sitting there in the parking lot with a giant hose running from its exhaust to the window.

8 The Crash

Cutler and Stan

The Crash is one of the most divisive episodes of Mad Men. Some people adore it, and others hate it, and it’s all for the exact same reason. The agency is visited by some type of doctor who gives the employees an “energy serum” – which is essentially just speed.

While it makes everyone extremely energetic and focused on their work, it also results in a range of bizarre occurrences like Don running through the halls and giving a rambling speech to his employees, Cutler and Stan chasing each other through the agency, and Ken tap-dancing while arguing with Don.

7 Ginsberg’s Meltdown

Michael Ginsberg was one of the greatest late additions to the series, as he didn’t appear until season five. Ginsberg snaps in the final season when a computer is brought into SCDP and takes over the creative lounge.

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Ginsberg grows paranoid and begins harboring resentment towards the computer, believing it to be brainwashing the employees. It culminates in Ginsberg’s mental decline, which sees him inappropriately coming on to Peggy and cutting off his own nipple. It’s mostly played for laughs, but it’s also incredibly shocking and upsetting to witness.

6 Miss Blankenship’s Death

Miss Blankenship

Don’s secretary Miss Blankenship was always played for laughs through her general incompetence. But things got even funnier upon her death. While obviously tragic, Blankenship’s death is largely played for laughs, and it begins with Peggy finding her “sleeping” in the chair.

The partners then try hiding her death from visiting business partners, which includes Pete and Joan wrapping her body in the chair and slowly wheeling her away while Ken and Don look on from the business meeting.

5 Pete And Bud Hate Their Mother

Bud discusses his mother

Pete and Bud make for a hilarious duo, with most of their comedic bickering stemming from their mutual hatred of their mother. In season two, the pair offhandedly joke about murdering their own mother, referencing Alfred Hitchcock’s Rope in the process – a movie about two men who seemingly pull off the perfect murder.

Later, they don’t seem to care about her mysterious cruise ship death or pursuing justice. Instead, they tell themselves that “she’s in the water with Father” and that “she loved the sea.”

4 Pete’s Constant Exasperation

Not great, Bob!

Throughout much of the series, Pete shows constant exasperation and isn’t afraid of flying off in a tantrum when things don’t go his way. Pete’s tantrums are often the source of some great comedy thanks to the writing and Vincent Kartheiser’s stellar performance.

Some of the greatest lines and scenes including the famous “Not great, Bob!” and “Hell’s bells, Trudy!” (complete with throwing an entire chicken off his apartment balcony), running too fast and falling down the stairs, and blowing up on Roger to the point that Roger simply hangs up on him.

3 Don Makes Roger Puke

Don is not a man to be messed with. After Roger flirts with Betty, Don gets him back by making him puke in front of some business partners. He takes Roger out to lunch and continuously feeds him martinis and oysters.

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He also pays off the elevator technician, forcing the out of shape Roger to climb 23 flights of stairs. His plan comes together in one of the show’s most disgusting visuals – with Roger hunched over the business partners, digested oyster and martinis spilling out of his mouth.

2 Roger Fires Burt

Roger fires Burt Peterson again

Roger takes delight in firing Burt Peterson, and his hatred results in one of the funniest scenes of the entire series. Much of the humor is derived from Roger’s total elation at firing Burt, which includes an ecstatic tone when saying “No, Burt, I’m letting you go again!”

But the scene also contains a ton of memorable one-liners from Roger, including “No one will ever say you weren’t funny, Bert!” (after Bert declares that his clients will leave with him) and “Probably doesn’t make a difference at this point, but no one fought for you.”

1 Peggy Blackmails Roger

Elisabeth Moss as Peggy Olson in Mad Men

The employees of SCDP certainly have a rapport, and that rapport involves blackmail. Roger comes to Peggy with some work and wants her to keep quiet about its origin. In return, he gives her $10.

However, Peggy wants more, and she essentially blackmails Roger into giving her money to ensure she keeps quiet. In the end, Roger ends up giving her $400 – just over $3,000 today.

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Updated: December 6, 2020 — 7:30 pm

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