Sketches (1992)

Terminally ill Cleveland resident Phil (Jason Bateman) arranges a get-together with his closest childhood pals, Gene (C. Thomas Howell) and Rob (Jonathan Silverman). Gene and Rob had a falling out over a woman, but they put aside their differences and agree to join Phil on a trip to Los Angeles. Their goal is to land Phil a spot as a game show contestant on "Jeopardy!" Along the way they find adventure and, in the form of spirited waitress Mary (Annie Potts), a new buddy.