3. Cool Runnings (1993)
Inspired by the true story of the first Jamaican bobsled team, Cool Runnings is a classic comedy that has become a modern Jamaican cultural reference. Everybody knows the film about four plucky Jamaicans who travel to Calgary for the Winter Olympics, overcoming numerous hardships and challenges on the way. There is now even a Kool Runnings water park and a bobsled ride (on tracks) in Jamaica. If you happen to be in Calgary, the real bobsled used by that actual team sits outside the reception of the Calgary Olympic Park. An underdog comedy with Jamaican spirit.