In 1984, Roper became the first and still only American to win an Isle of Man TT category on an internal combustion motorcycle, capturing the Historic 500cc class on his 1959 Matchless G50. Roper’s become a kind of folk hero among classic motorcycle racers for his speed and longevity. Through his longtime association with Rob Iannucci’s Team Obsolete, Roper has competed on some of the rarest and most exotic historic factory race bikes. Over close to a half-century of racing, Roper estimates he’s participated in more than 2000 events and won “probably about half of them.” During that time, he’s broken “20-25 bones.” Roper began racing at a 1972 Bridgehampton club event. He continues today (2018), more than 45 years later, still taking 40+ green flags a year. For how long? "I will retire when they pry my cold, dead fingers off the clip-ons,” he joked to MotorCycleNews.com, “But seriously, who knows. If I feel that I’m getting in the way, it’s time to retire." Roper is the subject of the upcoming documentary Motorcycle Man.