Brewster’s Millions (1985) | Planes, Trains and Automobiles (1987)

Brewster’s Millions

After losing his position as a minor-league pitcher, Montgomery Brewster (Richard Pryor) learns his great-uncle has left him $300 million. To inherit it, Brewster must spend $30 million in 30 days under a complicated set of rules that forbid him from donating too much to charity or retaining any new assets when the period is up. Unable to share details about the will's odd conditions with anyone, Brewster sets out to spend his money under the stern eye of paralegal Angela Drake (Lonette McKee).

Planes, Trains and Automobiles

Easily excitable Neal Page (Steve Martin) is somewhat of a control freak. Trying to get home to Chicago to spend Thanksgiving with his wife (Laila Robins) and kids, his flight is rerouted to a distant city in Kansas because of a freak snowstorm, and his sanity begins to fray. Worse yet, he is forced to bunk up with talkative Del Griffith (John Candy), whom he finds extremely annoying. Together they must overcome the insanity of holiday travel to reach their intended destination.