Now, this is a much more subjective question but one that we reckon we can give a conclusive answer on. If we are talking pure, not tweaked, no rotation ollies then it has to be the 1997 water tower ollie by Jeremy Wray. The Plan B skater managed to clear a 16-foot gap between two very large water towers with almost certain death awaiting him had he came up short. The pro skater managed to clear the gap with some comfort and with the most simple trick in the book, landed one of the most memorable tricks in the history of skating. So for that reason, this is the best ollie ever.