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The Jamaican national bobsleigh team represents Jamaica in international bobsledding competitions. The team first gained fame during their debut in the 1988 Winter Olympic Games in Calgary, Alberta, Canada,  where they were seen as underdogs as they represented a tropical nation in a winter sport. The team returned to the Winter Olympics again in 1992, 1994, 1998, 2002, and 2014. The team failed to qualify for the 2006 and 2010 Winter Olympics. Led by driver Winston Watts, Jamaica qualified for the 2014 Winter Olympics in the two-man bobsled. 
The team, consisting of Devon Harris, Dudley Stokes, Michael White, Freddy Powell, and last minute replacement Chris Stokes, debuted at the 1988 Winter Olympics in Calgary, Alberta. They quickly became very popular, largely because of their status as the ultimate 'underdog' story of the games. Alongside the novelty of a tropical country competing in a cold-weather sport, the team had very little experience going down a bobsled track, and borrowed spare sleds from other countries to compete. In a show of sporting camaraderie across national boundaries, other bobsledders were quick to give them guidance and support. They did not officially finish after losing control of the sled and crashing during one of their four runs. However, they showed significant improvement throughout the games and impressed observers with some fast starts.
The team returned to the Olympics in the 1992 Winter Olympics in Albertville, France, but finished poorly. They qualified again for the 1994 Winter Olympics in Lillehammer, Norway. There, the Jamaican four sled stunned many of their critics by finishing in 14th place, ahead of the United States, Russia, Australia and France.
In 2000, the Jamaican bobsleigh team won the gold medal at the World Push Championships in Monaco. At the 2002 Salt Lake City Winter Olympics, the 2-man team of Winston Watts (pilot) and Lascelles Brown (brakeman), set the Park City bobsled track record and the Olympic record for the push-start segment of the 2-man race at 4.78 seconds. Jamaica failed to qualify for the 2006 Winter Olympics in Turin, Italy, or the 2010 Winter Olympics in Vancouver, Canada. They did however, qualify for the 2014 Winter Olympics in Sochi, Russia as a two-man bobsled. 
Having qualified for the 2014 Sochi Olympics, but lacking funding, the cryptocurrency Dogecoin community raised on the team's behalf $30,000 of the approximately $40,000 required within two days. An online campaign was set up, seeking to raise an additional $80,000 through Tilt.com (formerly Crowdtilt) . When it closed on 22 January 2014, the campaign had raised $129,687, far surpassing the target.
The current team is available online:
Freddy Powell>Chris Stokes
The 1988 team was the inspiration for the film Cool Runnings (1993). The characters in the film are fictional, although original footage of the crash is used during the film. The film's depiction of the post-crash rescue was changed to show the bobsledders carrying the sled over the line on their shoulders for dramatic effect.
The 1988 team also inspired the reggae parody song Jamaican Bobsled by The Rock 'n' Roll Animals, played on the GTR radio station and later released on the CD Yatta, Yatta, Yatta. The song was recorded after Jamaica had announced that they would be entering a bobsledding team into the Olympics, but before the Olympics had actually started; nevertheless, the lyrics accurately predict that the team would crash during one of their runs.
The 1988 team was mentioned in Season 2, Episode 8 of Futurama. Fry commented that "They came in last at the Olympics then retired to promote alcoholic beverages." and Hermes agreed that they were "a true inspiration for the children."
The 2014 team was the inspiration for The Bobsled Song written by Sidney Mills from the reggae band Steel Pulse, Jon Notar and Groove Guild. The music video features 8-bit graphics. The song is timed to sync up to the team's Sochi bobsled run. The song was widely shown on television Olympics coverage in the lead-up to the team's run.