Exploring dozens of choices until you come up with right punchline

10 Screenwriting Tips You Can Learn from The Breakfast Club offers this advice on dialogue.

There are very few movies as quotable as The Breakfast Club. Part of that is because Hughes was an insanely talented dialogue writer. But I’ve read some of Hughes’ unproduced scripts, and believe it or not, he doesn’t always come up with the goods. That tells me he worked extra hard on Club. One of the keys to coming up with great lines and sharp dialogue is to challenge yourself, to not go with the easy first choice, but to keep digging until you find something original. Your initial idea for a line may be “What an asshole.” But with a little work, you could come up with “That man…is a brownie hound.” Instead of “Nice outfit buddy,” how about exploring 20 more choices until you come up with, “Does Barry Manilow know that you raid his wardrobe?” Dialogue is about challenging yourself. It’s about not taking the easy way out. Clearly, Hughes practiced this philosophy in Club.

Reminds me of coming up with punchlines. How you have to come up with 20 choices before you get that perfect line. I wrestle with that a lot. The first thing that occurs to me feels like the irght choice but a lot of times it's too obvious. Once I really push is when things get weirder/surprising/funnier.

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