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Luigi's Mansion easily. Probably 30+ playthroughs minimum. I remember playing it nonstop for a week with at least 6 or 7 playthroughs in a row before it got a bit boring.

In second place has to be Super Mario Sunshine. I'm unsure how many times I played through it but I used to play it at least twice a year back in the day.

In third place either Wind Waker or Super Mario Galaxy, at least half a dozen each.