Checking Out

Checking Out is a 1988 American comedy film, directed by David Leland and starring Jeff Daniels. It tells the story of a successful airline executive in his thirties who, despite a loving family and fulfilling career, experiences an existential crisis when his best friend unexpectedly dies of a heart attack.

Synopsis from Wikipedia, CC BY-SA 4.0. Everything below written here.

Poster © the film's rights holders.