A Goofy Movie (movie, 1995)

Though Goofy always means well, his amiable cluelessness and klutzy pratfalls regularly embarrass his awkward adolescent son, Max. When Max's lighthearted prank on his high-school principal finally gets his longtime crush, Roxanne, to notice him, he asks her on a date. Max's trouble at school convinces Goofy that he and the boy need to bond over a cross-country fishing trip like the one he took with his dad when he was Max's age, which throws a kink in his son's plans to impress Roxanne.