Up in the Air (2009)

Corporate downsizing expert Ryan Bingham spends his life in planes, airports, and hotels, but just as he’s about to reach a milestone of ten million frequent flyer miles, he meets a woman who causes him to rethink his transient life.

Director: Jason Reitman

Cast: George Clooney, Vera Farmiga, Anna Kendrick, Sam Elliott, Amy Morton, Jason Bateman, Melanie Lynskey, J.K. Simmons