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Interjection [ edit] cool runnings. Yow, mi a fly out tomorrow. I say we call it, 'cool runnings.' junior: Web the phrase 'cool runnings' literally means, 'go in peace' or, 'safe journey'. ( dated) all the best. Web the title of the song, “cool runnings,” is a popular phrase in jamaican patois that translates to “go with the flow”. Web loosely based on the unlikely true story of the jamaican bobsled team that participated in the 1988 winter olympics,. Web overall, “cool runnings” radiates positivity and reminds us of the importance of embracing joy, unity, and love in our lives. A useful salutation at the end of.