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Besides all the good tips above, make sure you’re not taking the work seriously and being way too responsible with the brief. This will kill the fun. It’s better to go too far and then pull back a little if needed than the other way around.
1000000% this
Take a stand up class. Learn the rhythms. And watch sketch comedy
Be startling. I think the most important thing about comedy is the surprise of the punchline. Whatever your setup may be, always push the expected outcome as far in another direction as you possibly can.
Yeah, what CD1 said. Especially the being a student of comedy sketch shows and comedians. Also, advertising in the 90’s and early aughts was much more focused on the funny, so revisiting CA’s from those decades can’t hurt if you want to get industry specific.
Highly recommend taking a improv class. You don’t have to be funny but it helps to make funny friends ❤️
And what if we all show up and nobody's the funny one?
When you find work you think is funny, literally transcribe it and analyze it. You’ll start to see patterns you can apply to your own work. Also, if you throw something out and it makes you laugh but it’s “too stupid” or off brief, explore it a little more.
Figure out what’s stupid or annoying and instead of being irritated, see why it’s funny.
Consume high quality (well-written) humor. Monty Python. Douglas Adams. John Hodgman. David Sedaris. If you find that you enjoy this kind of thing then you will consume more and get a feeling for it.