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64: Wing Cap. Metal was fun, but nothing beats that feeling of 3D freedom the first time you put the Wing Cap on.
SS: Turbo nozzle. Not too useful really, but such a blast to zoom around.
Galaxy: Ice Flower. Because ice skating was so damn fun.
Galaxy 2: Yoshi. He may not be a cap, but certainly a power up. The variety of uses and relative rarity made him fun.
3D Land: Tanooki w/stone power. For the nostalgia.
3D World: Cat Mario kind of by default. The levels were designed so that Cat was most useful.