Continuity mistake: In the film you see John Candy at the top of the Calgary Tower having Lunch. In the background you see a building called Bankers Hall which is slightly higher than the Calgary tower, that's fine except this was the 1988 Olympics, that building wasn't completed until late 1990.

Cool Runnings (1993)
Plot summary
Directed by: Jon Turteltaub
Starring: Doug E. Doug, John Candy, Leon, Malik Yoba, Rawle D. Lewis
When three Jamaican Olympic sprint contenders trip at the trials, they join up with another Jamaican to form Jamaica's first bobsled team to find another way to represent their country. This is the true story of four Jamaicans in the 1988 Olympics in Calgary, Alberta, Canada.
Sanka Coffie: Hey Derice! Ya dead?
Derice Bannock: No mon, I'm not dead. We have to finish the race.
Trivia: When Derice is applying for loans at different banks, the wall behind each bank manager is always the same wall! The plants and decorations are different, but it's the identical wall.
Question: In the true story of "Cool Runnings" did they really carry their sled to the finish line?
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Answer: The video footage of the crash was all real, but the racers did not carry the sled to the finish line, they walked in front of it as the Olympics crew/ team members pushed it behind them.