Factual error: The famous AFC Championship game that featured "The Drive" took place on January 11th, 1987, while the events of the film took place in 1986.
Hot Tub Time Machine (2010)
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Directed by: Steve Pink
Starring: John Cusack, Chevy Chase, Crispin Glover, Rob Corddry, Lizzy Caplan, Craig Robinson, Clark Duke
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Trivia: When the foursome ski down the mountain and are looking around at the oddly dressed people, someone behind John Cusack says, "Hey Lane, you owe me two dollars". This was a nudge to John Cusack, who played Lane Meyers in "Better Off Dead" and was pursued in the snow by a crazed paper boy shouting "Two dollars!"
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Chosen answer: The James Bond film "A View To A Kill" came out the year before in 1985. In the film, Bond's snowscooter is blown up by the Soviets, so he takes a wrecked ski from it and improvises it into a snowboard. Snowboards existed at the time, however, it wasn't until that film that their existence became well known. One year later in 1986, they'd still be very rare, but it's likely that his wasn't the first that the ski patrol had seen.
Captain Defenestrator