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When Tony Hawk was on the FOX version in Season 2 during a celebrity episode, Nathan (one of that season's class) had helped Tony out. Twice. As the show's credits ran, Tony walked to Nathan with the skateboard he skated onto the set on, and pulled out a Sharpie marker. Cue Nathan's eyes going wide as Tony autographed the skateboard for him. Doubles as a Heartwarming Moment.
The four times the top prize was won, twice on each version. The second $250,000 winner is also the only one to do so without using any cheats.