Bobsleigh - 1988 Calgary Winter Olympics - Men s Four Training The Jamaica team - Dudley Stokes, Devon Harris, Michael White, Chris Stokes - during the start phase in training at the Canada Olympic Park, Calgary. It was the first time Jamaica had entered the Winter Olympics in any sport. In their third run in the competition proper their bob overturned and slid down the track with the crew membersâÄ helmets scraping the ice wall. Thankfully the team were unhurt, and the image of them walking across the finish line alongside their bobsleigh became one of the enduring sights of the 1988 Olympics. Later their story was the loose basis for the film Cool Runnings .