When the boys travel back in time and open their suitcases to find Adam's filled with drugs, Jacob asks "Who are you, Hunter S. Thompson?" John Cusack was actually very good friends with Hunter S. Thompson. Cusack was also considered to play Hunter S. Thompson aka Raoul Duke, in the film Fear and Loathing in Las Vegas (1998), (before the role went to Johnny Depp), Most likely an in joke to when he replies "I thought I was."
When the guys first realize they're in the 80's and images are flashing up on the TV, there is one shot of Chevy Chase from his appearance in a Paul Simon music video "You Can Call me Al" from 1986 which is the year the movie is set. Chase plays the repair man in the movie.
One of the clips shown on TV, inside the ski lodge, is a Saturday Night Live sketch by Eddie Murphy. The classic skit has Murphy looking, singing and acting just like the legendary James Brown getting into his hot tub.
Crispin Glover, who plays the bellhop at the hotel, also starred as George McFly in Back to the Future (1985), another time-traveling movie that takes place partially in the mid-1980s. Additionally, he lost his arm in an accident whose cause isn't shown until the end, just like the cause of his son Marty's hand injury isn't explained until the end of Back to the Future III.
When the group first come down the mountain after confrontation with ski patrol they start to realize something strange is happening. After the man passes talking about being on a mountain on his cell phone, you hear somebody say "A bet's a bet I want my 2 dollars!" This is a reference to John Cusack's "Better off Dead". Through out the movie the paper boy continuously chases down John Cusack yelling for his 2 dollars.
Jacob makes a reference to the Stephen King novel The Shining. "I'm gonna make a prediction right now. One of us is gonna start writing a novel, and then we all get snowed in, and then Lou's gonna axe murder all of us." John Cusack previously starred in the movie 1408, which was based on a short story by Stephen King.
When the group first meets Blaine, Jacob says "hey look, it's the douchebag from karate kid." Rick who was betting against Lou in the bar was played by William Zabka, who was the rival of Ralph Macchio in the first karate kid movie.
As a fun inclusion for the fans, the light-blue Chevy pickup with the "sidestep" bed is just like the one the kids in Red Dawn (1984) used to escape into the woods, and Red Dawn is also the movie that inspires Blaine, the chief antagonist, to believe that the time travelers might actually be some kind of "21 Jump street communist spy battalion type dudes."
There are many anachronisms and plot holes in the movie. For example, when the guys get back to 2010, Lou shouldn't be there. He never went back and therefore would be in an endless cycle. These aren't necessarily goofs. The writers seem to be playing fast and loose with the 80's, and obviously don't care about holes for the sake of comedy.