Someone on the Internet has written fan fiction called "The Sins of the Fathers," imagining a romance between 30 Rock's Jack Donaghy (Alec Baldwin) and Mad Men's Sally Draper, making it not-gross by placing it in 1990, when they are both young Manhattan professionals. Jack and Don actually meet! It's kind of long and partially about psychiatry, so here are some choice selections for the discriminating Mad Men and 30 Rock fan.
"Sally turned out to be an English teacher at a Montessori school on the Upper West Side, but this slightly unpleasant revelation was not enough to make Jack reconsider."
"Of course, Gene was just a baby [when the divorce happened], but for Bobby and me it was ... See, my mother isn't what you would call a nurturing person."
"It would be great for you to sit down and talk with someone about that," she said, and just like that, he knew he was going to go to bed with Sally Draper."
"So this was Sally Draper at the moment of ecstasy, Jack thought as he lowered himself to his knees."
"By late July, the microwaves division had actually dropped 3% in overall market share. "So, what's the latest news, Jack?" Geiss asked — lightly, but unmistakably serious."
"Jeez," Sally said, her palms pressing into Jack's shoulders as she straddled his back. "I never met anyone so tense."
But listen, about this microwave thing. You should talk to my father."
"I thought you didn't talk to your father."
"I talk to him, I just don't — you know, talk to him. We're not close, but we're not estranged or anything. Anyway, he was in advertising for a long time, and I know it still interests him..."
"Oh my God," Jack said. "Your father isn't — "
"Don Draper," Sally said. "Oh no, don't tell me."
In response, Jack stood up, dusting off his pants, and pulled a book off one of the shelves lining the room. Zen and the Ad Man, by Don Draper. Copyright 1981, a little late for that kind of gender-specific language, which was one of the things Jack loved about it."
[Meeting Don Draper] "Jack shook his head, amazed. God, it was like watching the Harlem Globetrotters spinning basketballs on their fingers. You just couldn't look away."
So, Don ends up really helping Jack with microwave marketing, and then Don is diagnosed with lung cancer. :(
Fic: The Sins of the Fathers [lz1982 LiveJournal]