I fine-tuned the newly released OpenAI GPT-2 345M model on all dialogues (Season 1 to 9, around 3MB) of ‘The Office’ and the model starts to acquire some humour, at least when reading it through the lens of the specific characters.
Some of my favourites:

“Michael: What is the most important thing for a company? Is it the cash flow? Is it the inventory? Oh, it’s the closets? The closets are the best.”
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“Michael: All right, time for another round of questions. First, how old are you?”
“Phyllis: I’m 58. “
“Oscar: 58? “
“Kevin: Hey, hey, that’s old, right? Can I get a raise?”

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“Andy: This book’s worth more to me than any number of my books. I mean, I don’t care. One of them is a good book, the other is a bad book, and the next one is a joke. All right? So… my money’s on one of the two, or zero, as they say in French, so that’s fine. “

I published some more here and will add some after training the model for a bit longer:

–> https://twitter.com/fateful_by

Some things I already noticed:

• It got really dark at some points, e.g. “Darryl: I’m going to take a little piece of ice. I’m going to stab it into your skull.” or “Dwight: [in Andy’s car] You know, I’ve always wanted to be a detective. So, when I come back, I’m gonna sniff out leads. And if I catch a murderer, I’m gonna go blow my brains out. Now, I don’t know how that works. But I think I might be the best person to go out there and catch one of those serial killers. “
• Temperature setting above 0.7 gives some really crazy outputs, e.g. “Andy: Stanley Hudson! [throws tie to Dwight, who throws it back] Dwight: Sorry, I didn’t mean to upset you. Ralph knows best. [to Creed] What’s gay is who you know and what’s deb (back to Oscar) You can’t work here. You’re a too busy hand. [back to Toby] You were fired for stealing the pen, right? Toby: Yesss! Bring it on!“