"One Fine Day" (1996)
Some of Clooney's characters are men you want to detest but can't, but in this (albeit predictable) romantic comedy, columnist and single parent Jack Taylor is a man you love to love. Over the course of 24 hours, he and another single parent, architect Melanie (Michelle Pfeiffer) meet and fall in love. In a single day, Taylor takes care of Melanie’s son, buys his daughter a kitten, and tries to show this hardworking single mother that there's still humor in the world. After a day like that, who wouldn’t fall for him?