Uncle Buck (1989)

When Bob (Garrett M. Brown) and Cindy Russell (Elaine Bromka) have to leave town for a family emergency, they are left with no alternative but to call in Bob's brother, Buck (John Candy), to baby-sit. A jobless, lifelong bachelor with a heart of gold, Buck hardly seems the ideal baby-sitter. Charged with caring for his smart-mouthed teenage niece, Tia (Jean Louisa Kelly), and her two outspoken younger siblings, Maisy (Gaby Hoffman) and Miles (Macaulay Culkin), Buck finds himself learning how to survive in suburbia and parent at the same time. At first Buck doesn't even know how many times a day to feed the dog, much less the kids. He battles the washing machine and sends Miles to school with an utterly inedible bag lunch. But little by little Buck begins to take his responsibility seriously, putting the needs of his nieces and nephew before his own, earning their love and respect. With any luck, his newfound familial instincts will help him win back his estranged girlfriend, Chanice (Amy Madigan), who is tired of his refusal to commit to marriage. Directed by John Hughes (SIXTEEN CANDLES, THE BREAKFAST CLUB), this film was shot in various Illinois locations.