Hoilett represented Jamaica in the 440 yards (400m) at various championships, with the 1964 Olympics being the pinnacle of his career.

"Rupert was known as a hard worker with talent to boot. He was good enough to make the Olympic team even as a Kingston College schoolboy coming out of Boys Championships," said Garth Gayle. "We owe our current successes to athletes like Hoilett who toiled hard for success and lifted the name of Jamaica even when there was not much to gain from the sport. May his soul rest in eternal peace. Condolences to his family and friends," concluded Gayle.

Hoilett came to public attention at the Boys Championships when he won the the 440 yards race in 49.3 seconds, which at the time was the first sub-50-second clocking in the history of the event.

He would later book a place on the Jamaica team to Tokyo Olympics with an improved 49.1 seconds and was given the honour of carrying the nation's flag during the opening ceremonies.

In 2019, Hoilett’s property on Skibo Avenue in Kingston was damaged by fire.