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I have to say Xbox. I enjoyed far more titles on it than on the N64.

N64:

Pro:
Made 4-player splitscreen awesome in a big way.
Introduced rumble
A handful of GREAT exclusive titles

Con:
EXPENSIVE games
Lackluster catalog of games beyond the core titles
Blurry graphics
Odd controller


Xbox

Pro:
Xbox Live
LAN multiplayer
Great graphics
A handful of great exclusives
Almost always the best version of multiplatform games
Custom music

Con:
Not as supported as the PS2
Not all exclusives worth their salt (Kakuto Chojin, etc.)

I loved my N64 and some of its games, but at the time, it was not a great system to own as the good games were few and far between. I remember struggling to find games to buy for it. While there were quite a few 5-star games, they didn't have the vast number second-tier, four-star games that the PS1 or the Xbox had.


Xbox is the winner in my book.