The current iteration of the World's Heavyweight Championship reminds me of Triple H's dominance and multiple reigns as champion on RAW. He is the key person responsible for the belt's prestige. I also associate Edge and Batista with the belt after it was drafted to the superior brand - Smackdown.
As a kid, I always visioned Bret Hart with the classic belt.
I started watching wrestling again in 2002 due to Brock Lesnar. I've always associated the undisputed belt with Brock Lesnar. The second closest (for me) is JBL for the crazy long reign he had.
John Cena created the spinner belt and has had it more than anyone on planet earth.
Although I had stopped watching wrestling at the time, the attitude era WWF Championship reminds me of Stone Cold Steve Austin.