Honesty flies the ship here. It can either be from the whole truth, or the kernel. You could go for something over-the-top and funny that's total bullshit, but comes from an honest escalated state. The hard part about humor, if you're deadly serious about it as I am is being non-derivative. Taking into account how many pathetic sex jokes you see at stand-up routines across the country, most people, including an inordinate amount of stand-up comics save the top 2-3% are actually even remotely funny by honest standards.
You approach obviously depends on your audience - I'm extremely partial to John Mulaney as a favorite because he's a phenomenal storyteller who knows how to use emphasis to turn an ordinary story into a shocker that's bound to get a laugh. He's also a word-player, which works extremely well with tonal inflection. How you shape and say your lines is five times more important than what you're actually saying.
Working from rage and loneliness, while counterintuitive can be hysterical if you're willing to pay the price in confidence, but bear in mind that adhering strictly to this method can trap you in a cycle of self-destructive approval seeking. There is a lot of deep self-inquiry that goes into great humor.
The funniest thing I've heard as of late came to me through my awakening experience. The name I was born with means the house built for the love and grace of the gods, and Greco-Norse mythology has always been my interest. On top of that, both my parents are doctors (sworn by the hippocratic oath) so I'm a magnet for these entities during my shadow work. I've learned to befriend and familiarize myself with several.
One day I was contemplating the path of my life, most particularly how I'd like to die - dark humor has always been a favorite of mine, and if I can get roasted, even better. Since spaghettification by black hole seems unlikely unless an alien race with superior technology comes to visit us, I figured the most spectacular way to go would be to get a blood eagle on top of Mount Olympus. When I talked to Zeus about it, you know what he said?
"Get your fat ass outside and exercise because nobody wants to see your saggy tits on top of my mountain."
Ouch.
As a post-note, I can unpack this A LOT because this is my area of study, from absurdist philosophy to general wisecracking. Likely more so than Leo (in this area), because art is all I focus on. On top of that, I learned from a young age that being funny enough allows you to get away with everything. Tension, timing and awareness are the elements always at play among others. But I'll wait for a response before I go further.