Plot hole: The movie is based in 1986 after the group time travels from 2010. That makes it a 24 year trip back in time. It is stated that Jacob is 20 years old. That is an error as this would make him roughly around 23 or 24 if he was conceived in 1986, which we saw near the end of the movie.
Hot Tub Time Machine (2010)
Directed by: Steve Pink
Starring: John Cusack, Chevy Chase, Crispin Glover, Rob Corddry, Lizzy Caplan, Craig Robinson, Clark Duke
Lou is a party animal without the party. Adam has just been brutally dumped by his girlfriend. His nephew Jacob won't leave the basement. Nick's career and marriage are circling the drain. Disappointed with how their lives have ended up, the four friends decide to go to the old ski lodge where they spent their glory days. However, after a wild party in the hot tub, they find themselves IN their glory days. The hot tub is really a Hot Tub Time Machine, and has transported them back to 1986. They soon come to realize that they must literally relive their glory days exactly as they did to prevent a time paradox. However, some of them stray from the plan rather drastically...
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!"
Question: When the four main guys are first coming down the slope in 1986, the two from the ski patrol apparently don't recognize Jacob's snowboard. Though snowboards were still largely unknown in 1986, wouldn't someone who worked for a popular ski resort recognize them?
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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.