And yet it seems he took little pleasure in his incredible achievements.
Obree admits that his fear of failing, rather than a desire to succeed, was the biggest motivating factor for him when he competed. Since retiring he has been diagnosed as having bi-polar disorder, a condition that affects the sufferer's mental state.
"When I broke the hour record it was my attempt to meet the expectation to feel worthy as a human being. I felt total relief when I heard the gun go off, meaning I had passed Moser's distance.
"It was the sound of a glass ceiling shattering - no matter what happened after this, I would still be the person who broke the hour and no-one could take that from me."
Obree lists his victory in the pursuit at the World Championships in Colombia in 1995 as the one that brought him greatest pleasure in his career, not simply for winning the coveted rainbow jersey in itself but as a settling of scores with the president of the UCI, cycling's governing body, Hein Verbruggen who had unjustly disqualified him in the previous year's competition with a rule change passed the night before Obree rode. Verbruggen was trackside at the race in Bogota.
"My happiest moment was probably winning the world's in Colombia. It was an added incentive to win that Verbruggen was there to present the medals."
Yet more than the frustration of having his riding position banned not once but twice, Obree regrets that he never followed Boardman into the professional peloton and so missed a chance to ride the Tour de France prologue. He was hired by French team Le Groupement in late 1994 but was fired two days later in mysterious circumstances with Obree not having ridden one race for the team.
"The thing that frustrates me most looking back on my career was not being able to ride the Tour de France. I would have loved to have ridden the prologue and I think I would have had a good chance of winning it."
Obree is at present keeping himself busy by writing a training manual and getting himself in condition to play the part of his legs in the close-ups in the film of his remarkable life.