Street Fighter II TURBO...Set difficulty to all stars and you must not let anyone win a round on you. I accomplished this long ago with Guile or Ken. You get their ending, the long credits with the world warriors destroying boxes with their moves, the "You've Mastered
insert Street Fighter character here!!" picture, and the group picture. Now, can someone say Sagat is a cheap little girl who stands in the corner throwing out Tigers and when you move in for an attack, executes his Tiger Uppercut...
Also aside from Street Fighter in SNES, I also had difficulty with the secret boss known as Lapis from
Legend of Legaia atop Mt Letona. First it seals all your magic, it always gets the first turn and deals a total of 13 attacks that each take off over 1000 of your health. The max health you could ever have with LV.99 is 9999HP. If you win, you obtain a Devil's Medallion that berserks your character, so you have no control over him/her, that randomizes their arts over and over again. The process is random, so your character may only execute one move and stop, while one time one of my characters did about 30 arts moves that dealt over 40,000 damage