I’m gonna say Mullen, Way, Tony, Gonz, koston, and Daewon could all be argued for pre 2000 but in different ways. Mullen might seem like the misfit in that group, but I’ve heard from multiple accounts he could do head high backside airs and 5-6 second held andrechts on 12 foot vert ramps in 82-84. Obviously in terms of technical street, him, koston, and daewon owned the nineties. Obviously Rodney Mullen is the greatest freestyler ever period, invented most technical street flips, pretty much is the only guy who can combine freestyle and street to that level. All the other kids who have tried like Kilian Martin, Connor Burke, Andy Anderson, Alexander Rademaker cannot do what Rodney does at his level of precision, technicality, and overall skill level of his freestyle/street hybrid. Which is why I say Rodney prolly wins the overall because he hits check boxes. Best freestyler ever period. Could professionally compete in vert in the 80s if he really wanted to. One of the best technical street skaters ever who invented most flip tricks in street. He also can combine freestyle and street like no one else.