#1 Ken Shamrock
It’s hard to tell if Ken Shamrock ever actually retired even now as a 50 year old man. You could argue he retired the first time all the way back at UFC 9, and has been coming back periodically, when people would pay him to, ever since.
The Great Greg Howard wrote a piece on Ken Shamrock called which called him “The World’s Most Dangerous Can” which says more than I ever could about his comebacks and the success thereof.
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The reason I put Ken Shamrock number one is because while the rest of this list is retired, or going to be retired within a week or so, Ken Shamrock is sitting somewhere, waiting for the phone to ring.