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Four pals are stuck in a rut in adulthood: Adam has just been dumped, Lou is a hopeless party animal, Craig is a henpecked husband, and Jacob does nothing but play video games in his basement. But they get a chance to brighten their future by changing their past after a night of heavy drinking in a ski-resort hot tub results in their waking up in 1986.
When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.
A day in the life of a Chicago cab driver is examined as he picks up fares from the good and bad parts of the city and emotionally connects to many of his passengers.
Martin Blank is a hitman for hire. When he starts to develop a conscience, he botches a couple of routine jobs. On the advice of his secretary and his psychiatrist, he decides to attend his ten-year high school reunion in Grosse Pointe, Michigan.
