Chess Master or Starcraft.

I have absolutely no clue.

I think Windwaker and OoT are probably both around 6-8 times.
RE4Wii is already over that though if you only talk main game files (about 10-12 I think)
Banjo-Tooie possibly around 6 times.

----
So it is RE4:Wii I suppose.

Starcraft or FF6... no idea how many times.

I've beat Tetris Attack the most. It only takes about an hour since it's a puzzle game, and I've had it for almost 10 years. Suffice it to say that I've gotten a lot of play time out of it.

Super Mario World dont know how many times I beat it but it has to have been more than 15 times.

Mine was probably Bubble Bobble on the NES and I seriously can't remember how many times I probably beat this game.

I don't beat very many games but I beat Pokemon like 4 times

Usually I just get a new game after I beat a game...
Unless I don't have the $ and is very bored...

Breath of Fire 1, 5 times.

The Legend of Zelda a Link to the Past: 20 times
Mario Bros 3: about 8
Star Fox: More times then I can count

If you don't count fighters, i guess i beat TMNT: turtles in time 15+ times. House of the Dead 2 probably 10+ times.

As far as longer games (5+ hours), i don't know if ive ever played a game front to back more then 3 times.