Halo 2 on Legendary by far.
Thing is with Reach is you had AI buddies who basically had unlimited health, and I used the whole "Shoot a couple of guys, cover, rinse and repeat!" tactics and beat it on legendary in less then two days alone.
Halo 3 was tough, but nothing comes close to Halo 2 on legendary IMHO. Hope to god if they do a HD facelift to Halo 2 that theres no solo achievement for legendary, cause that would be a bitch.
It's just that simple.