A Literary Survey of “Mad Men” Fan Fiction

Mad Men takes place in a rich, fictional universe called the ‘60s. Kevin Nguyen takes a look at a few of fanfic’s best offerings.

“Ten Years and Change” by FanWriterWV

fanficDon Draper wakes up in the hospital after having been in a coma for ten years. He’s visited by all of his friends at Sterling Cooper. Peggy is successful. Sal is out and about. Betty has left Henry Francis, and ready to get back together with Don. In fact, everything has worked out for everyone. Except Pete Campbell, who has died under circumstances ambiguously referred to as the “accident.”

Three things that happen in the story that are left unexplained:

  • How Don fell into a coma
  • How Pete died
  • Why Paul Kinsey won a Hugo Award

“Portrait of a One Night Stand” by kasviel

The title of this one is funny: by “Portrait,” kasviel means 10,000 words, and by “One Night Stand,” he means a disturbing scene wherein Don beats Pete with a wooden paddle.

Pete watched the man rifle through his things, baffled and a bit concerned. “Then, what are you going to do?”

Don turned to him, holding his old fraternity paddle. Realization dawned on Pete’s face, having to compete with his perturbed expression. “You’re going to spank me.”

“Yes,” Don said certainly. “I’m going to spank you.”

After a long, brutal pummeling of his buttocks, Pete admits that he is love with Don, and receives a different long, brutal pummeling of his buttocks.

(Also worth noting that since Don never attended college, it’s inconsistent with the Mad Men universe that he would own a fraternity paddle.)

“Don and Betty: First Meeting” by gilmoregossiplover

This imagining of Don and Betty’s first encounter takes place at a photo shoot where Betty is modeling for an ad to be used by one of Sterling Cooper’s clients. Don introduces himself to Betty, but discovers that she already has a boyfriend, Tyler.

Don sends her flowers every day for the next week. Then he shows up at her apartment with a brand new fur coat. Betty explains that she has just dumped Tyler, and the two go out for coffee.


“Leave it to Beaver” by The Modren Man

In this 300-word piece, Betty contemplates whether she should stay with Don after discovering that he has been unfaithful by comparing her life to Leave it to Beaver (“June Cleaver’s husband doesn’t cheat on her.”). At the very least, this short story is about as romantic as Leave it to Beaver:

[Don] turns me around and stares me in the eye. He whispers “I love you,” pounding his lips on mine, bruising them in the process.

“The Plan” by Day Man

This M-rated gem is told from the perspective of Roger Sterling. It opens with:

I want to fuck Don Draper.

And shortly afterward:

Oh God, he’s wearing some cologne that is driving me nuts! He sits in front of my desk and puts a cigarette in his mouth. I wish my dick was that cigarette.

Before Don says:

Suck my cock Sterling.


I’m ready to fuck you.

And then some other stuff happens that I NEVER WANT TO THINK ABOUT AGAIN.

“The Adventures of the Sterling Cooper Kids: The Ghost of Sterling Sr. – Chapter 1” by Paranoid Emo Ranger

In what appears to be a cross between Mad Men and Scooby-Doo!, Peggy, Pete, Sal, Kinsey, and Cosgrove decide to stay late after work to see if there’s any truth behind the rumors that the ghost of Sterling Senior haunts the Sterling Cooper office.

I believe Paranoid Emo Ranger best captured Paul Kinsey out of any fanfic writer.

Paul looked at the picture of his girl Sheila and gobbled up the chips on his hand, she’s beautiful he said to himself and ate some more chips.

Also, there’s some carefully crafted suspense right at the end:

Ken was about to open his mouth when someone tapped him on the shoulder.


When he turned around it was a decapitated hand that floated around.

“Oh! Run! Get up from the carpet run!”

Unfortunately, the story ends there, as Paranoid Emo Ranger never completed anything after chapter one.

Kevin Nguyen is a founding editor of The Bygone Bureau. His only marketable skill is an above-average knowledge of European geography. He has been useless since the introduction of the atlas in 1477. Reach him by email or follow his Twitter account.