What is the most challenging video game?

I'm looking for a really challenging video game to get my boyfriend for Christmas.

All the other games that most people would find challenging, he beats with almost no difficulty.

He's always complaining that there are no good enough games for him because he always beat them in less then a week.

He has PlayStation 2 (PS2), Classic Super Nintendo (NES), Nintendo Wii, Xbox360, and a Nintendo DS.What is the most challenging video game?Devil May Cry 3 for the PS2 is incredibly difficult on the higher difficulty settings, so I think he will get enjoyment out of that.What is the most challenging video game?
HAHA well the "most challenging game in the world" is actually a very small 64mb computer game, it is called "i wanna be the guy" this is free, it is not like 360 games or such, but it is the worlds hardest game, it is a combo of old side scroller mario's mixed with a flustercuck of other side scrollers.What is the most challenging video game?Ninja Gaiden (the NES or Black for the Xbox NOT II), Battletoads is like getting raped as well. Try those. Don't bother with any of the others (except maybe Devil May Cry 3), as any child with Aspergers Syndrome could destroy them, apparently these people all suck. NOTE: Portal isn't even hard for a ******* Gibbon, maybe the guy who recommended it was dropped as a child.
Contra 4 (DS) will stop his complaining. I still haven't got past level 2 on normal, and I've been gaming since the NES days.What is the most challenging video game?The Orange Box - Portal, is incredibly hard, i gave up after about a week but i think its only on computer though. Half Life 2 is pretty damn frustrating as well.What is the most challenging video game?
I recomend Ninja Gaiden 2 on it's hardest difficulty.
Ninja Gaiden II is supposed to be pretty tough.

Devil May Cry 2.What is the most challenging video game?
bioshock
Halo Wars (xbox 360). I think its challenging;)