Terminal Velocity (1994)

Synopsis
Party-hard skydiving teacher Ditch Brodie (Charlie Sheen) has a knack for getting himself into trouble, but his booze-babes-and-planes shenanigans hardly prepare him for an international plot that pits Brodie and a mysterious KGB agent against a post-Cold War Russian villain called Kerr (Chris McDonald) and an American heavy named Ben Pinkwater (James Gandolfini). Aerial set pieces alternate with tongue-in-cheek flirtation and conspiracy-theory suspense as Brodie meets a beautiful new student, Chris Morrow (Nastassja Kinski), then must try to explain to the authorities how he allowed her to fall out of a plane to her death. Soon Brodie -- on the run from both Kerr and the police -- begins to realize that in espionage, as in romance, often nothing is as it seems. ~ Brian J. Dillard, All Movie Guide