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UnderwaterFunktown said:

20) I AM THE LAW

19) To the top of the island

18) I can't believe they changed Mike...

17) To the top of the mountain

16) Looks can be decieving and this little white cat has got moves like a Smash Bros. figther

15) Blue hair anime chain gang

14) Speaking of small white characters in Smash Bros... This guy's sort of in

13) An Earthbound-like with black and white horror elements

12) Color Your Night

11) It's one of those games where you have to put the year in the title but I just like to call it IV

20: Judge Dredd: Dredd vs Death maybe?

19: Link's Awakening? 17 might also fit, but since it's on an island, I presume it's this one.

18: Punch Out!

13: Undertale? Though 14 might also fit if you consider Sans costume...

12: Night into Dreams?