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Clearing the True Arena in Kirby: Planet Robobot with Mirror. (May have lost it on the final battle, but basically the whole way.) Chose it for power, not for challenge. Looked around Youtube for what others did. Does not recall seeing Mirror. Seemed kind of special.
Beating Nethack. Just...at all. Relied heavily on guides because of the insta-death possibilities. Felt good, nevertheless.
Defeating 7-star Hisuian Typhlosion with Luvdisc solo in a Tera Raid. How often does anyone accomplish anything with this Pokemon? Hits as hard physically as known powerhouses Sunkern, Budew, and Combee. Races a timer as well.
Beating Ness's Nightmare in Earthbound with no equipment. Probably made it harder than it should have been. Went in with 2 Bags of Dragonite instead of 3 (maybe?). Ran out of healing and PP when Ness's Nightmare ran dry on PP. Punched it down for the last bit of its health. Could have died to a 37.5% chance insta-kill at least twice.
Thought of some others. Tended to be more grindy than difficult.
When I did that charity challenge thing in FF V for my challenge one month, I ended up with an awful selection of jobs and not nearly enough time. I beat the game with literally like 5 minutes to spare. Best I've got right now.