I hear you, Zac!
A big part of what’s funny about “word entrepreneur” to me is that it makes fun of how lightly the word entrepreneur is thrown around nowadays. I talk about it in this post: https://medium.com/maison-with-a-pen-blog/the-internets-worst-business-advice-and-what-to-do-instead-746935479cea (it’s #6 on that list).
It may be a controversial opinion but this article spoke to me about the word entrepreneur: http://www.irishtimes.com/business/technology/overuse-of-word-entrepreneur-has-leached-it-of-all-meaning-1.2345780
So part of the jokes are anti-humor, yes. Part of the jokes are just being ridiculous and using toilet talk like cooter and boner. Which is a party in itself.
But a big part of it is making fun of the word entrepreneur, as if I’m saying I’m breaking incredible ground in language by smashing 2 words together. The joke is that I think I’m being smart and witty and an innovative linguist by creating new words for things—but they unwittingly become ridiculously dirty or offensive. That’s the contrast I was going for. So for me it’s really not about puns at all. It’s about the contrast; the fake puns are a way to get there.
It’s similar to the contrasts I drew in the LIT AF literary tweets. Smashing 2 things together like literary smarts + millennial slang = funny. To me, at least. Likewise the pretentiousness of the word entrepreneur is great for pairing with accidental toilet talk.
I don’t really understand what you’re saying about the pun reversal thing and working out the kinks because honestly those jokes made me laugh my ass off and did okay on Twitter so I’m pretty happy with them as is. I appreciate you sharing your thoughts, though :)
I‘m familiar with Swifties but I haven’t practiced much with them. I’m not a big pun person and that kind of humor just doesn’t do it for me. But I’m sure it’s still great writing practice. Thanks again, Zac!