Like an honest Good Charity whose cause they believe in.
That way, you'll have done a nice thing in their name but they'll be a piece of shit for feeling bad about it when they find out what you did instead of giving them the money directly.
It's a gift so of course you let them have the tax receipt. That way sometime next year they'll end up getting 17% back of that as a refund on the taxes they had already paid.
Funny story, my uncle did something similar once as a gag gift for me and my siblings. He gave us each a wad of industrial shrink wrap (the kind used to wrap heavy machinery like boats for storage) with like $100 in coins inside. He had actually heat-gunned it to stick it all together. We had to spend the next day pulling it apart to get all the loonies and toonies out
A glitterbomb and a donation to something they really don’t like. A stripper of the gender they’re not interested in. If they’re italian, throw in a square-shaped pineapple pizza, too.
5x $20 lottery tickets. Most lottery tickets have a 1:3 - 1:5 win rate, so if you're lucky enough he might win literally nothing. Nothing else on this list gives the friend hope. Hope unfulfilled is the definition of cruelty.
A goldfish. Just the fish. Ask them to name it on the spot so they have to keep it. Now they need to rearrange their home to make space, and buy a tank and such for it.
Plus, it's cheap, so not much of a refund going on if they decide to just give it back.
If the friend is Chinese or East Asian, buy a black picture frame with a black and white picture of them already mounted. Or buy them a set of knives. Or give them money in a white envelope.
There was a company once specilized in delivering boxes full of the shit (meaning feces) of your choice to your chosen special person, it was called something like "shitexpress"
Assuming you are just a horrible person: Buy them gympie gympie leaves, toss them in a gift bag, and don't tell them what they are but that their present is in the leaves.