Coolness and rarity-wise, it would be the 1969 Topps #567 Pirates Rookies 'no black outline' variation, which is monstrously hard to find, and for pure joy and nostalgia, the earliest card I recall from my youth (and it puts a smile on my face every time I see one) is the 1972 Topps #49 Willie Mays.
Pure awesomehood!
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