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Glad I read through other posts first. This was going to be my answer! On the original NES I never got close to beating Mike Tyson. I was only able to beat Super Macho Man twice, and promptly got destroyed by Tyson!
The Switch online version might be nice because (I think?) you can save? But on the original NES version, you had to start over and beat all 13 fights just to try again. It was brutal!
Probably a few of the bosses in Pokémon: Gale of Darkness. I remember the last, second last, and the guy dressed as a wizard being the most difficult for me.
That last one was so rough, esspecially since you are susposed to take all the shadow Pokémon, and all of the last guy's Pokémon are shadowed up. It was super hard. Since you basically just snatching up each of them one at a time.
But I will admit the Kongdom Heart's 2 bosses had me going crazy.