Here's my personal top 10 in order of difficulty (10 easiest 1 hard as all hell)
10 - 121 Stars in Super Mario Galaxy with both Mario and Luigi
Pretty easy, just had to master jumping with Luigi, the last few purple coins are the only frustrating parts.
9 - Beating Zelda II: The Adventure Of Link with only 7 game overs
Iv played this game 4 times now and every time my total number of deaths goes down by about 10.
8 - 100% completion in Donkey Kong Country and Donkey Kong Country 3: Dixie Kong's Double Trouble
I could 100% DKC 3 since I was a kid, DKC I only recently got but found all the bonuses pretty easy. Only DKC 2 to go.
7 - 100% completion in Metroid, Metroid: Fusion, Metroid Prime, Metroid Prime: Hunters and Metroid Prime 3: Corruption
Pretty easy, just got to remember where everything is.
6 - Completing Virtual Boy: Wario Land in one sitting (3 hours)
Gave me a nasty headache.
5 - Beating Super Mario Bros.: The Lost Levels
After beating this, I consider myself a master of 2D platformers.
4 - All trophies in Super Smash Bros. Melee and Super Smash Bros. Brawl
Boss Battles on intense still gives me nightmares, I staid up all getting that trophy. (Thank Meta Knight)
3 - All cheats unlocked in Goldeneye 007
As a kid I thought some these cheats were impossible, now I get em all pretty easily.
2 - Having some AX racers unlocked in F-Zero: GX
That's right, I only have 3 AX racers unlocked so far and have beaten to GP's on the hardest difficulty, and I'm very proud of that feat.
1 - Unlocking everything in Time Splitters 2 and Time Splitters: Future Perfect
Getting all the platinum trophies in these games was the hardest thing I ever did, but I did it.