Here’s my choices:
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Duncan Imperial wood (1954) – I figure nothing really changed on wooden yo-yos since Flores (1928) invented the string loop on a wood axle, and the Duncan was the best known and most widely disseminated wood yo-yo, so I’m going with that.
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Tom Kuhn No Jive 3-in-1 (1978) – the first “modern” wood yo-yo, it can be disassembled, has an easily replaceable axle, and even flipped to Butterfly.
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Tom Kuhn SB-2 (1990) – the first ball bearing all metal yo-yo with response pads (turbo disks). Shows the evolution to “wheel” geometry versus Imperial or Butterfly, too.
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Turbo Bumble Bee (1997) – the first mainstream plastic with ball bearing and modern-ish similar-to-silicone (cork) response pads. This model is the foundation of the last yo-yo boom in 1999, but note that it’s still narrow wheel looping geometry.
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Hitman (2003) – the first mainstream ball bearing, silicone response, wide and wide gap yo-yo, every yo-yo after this would follow in the footsteps of what the Hitman laid out.