Cowboy Bebop I've watched 10+ times
Trigun Ive watched twice, once subbed once dubbed. Subbed so much better
Deathnote I've watched twice, maybe again someday.
Interstella 5555 I've watched 4 times now.
Samurai Champloo I've watched twice, going to watch again.
I really want to watch Eden of the East again.
If counting seeing nearly every episode on TV, I've basically seen Inuyasha twice.
I want to watch Haruhi Suzumiya again.
If were counting non anime, I've seen every episode of Futurama at least 3 times.