Boitano and Brook Shields at the People's Choice Awards, 1988
1. Boitano got his skating start as a "daredevil roller skater on the sidewalks of Sunnyvale, Calif." Eventually, he started pretending that his driveway was ice, and he'd pretend he was skating as Rudolph Valentino (with a cape, of course), starring in a show with Peggy Flemming. He wore his skates into the ground — even after they became too small for his feet, he cut holes in the boots of the skates to accommodate his growing body. By the time he was 8 and a half, he entered his first ice competition, in the Pixie Derby Boys division.