Angel on Abbey Street (1999)

An amiable and benign hobo named Briefcase makes his living by claiming to be the Tooth Fairy and asking passersby to fund his business. Most folks enjoy Briefcase's playful ruse, but he soon meets his match in the form of a pragmatic young girl named Lisbeth. When Briefcase learns that Lisbeth doesn't believe in the Tooth Fairy, he takes it upon himself to show her a world full of magic.