Kikujiro (1999)

Kikujiro (1999) is set in contemporary Tokyo, where Masao, a lonely only child, resides with his grandmother. When his sole friend departs for summer vacation, Masao discovers a photograph of his mother with an address and decides to embark on a journey to find her. Miki, a friend of his grandmother, enlists her husband, the yakuza Kikujiro, to accompany Masao on his quest. Their adventure begins at bike races, where Kikujiro loses all his money, but Masao surprisingly picks three winners. Kikujiro then spends the winnings on a peculiar cycling outfit for Masao and the rest at a hostess bar. The next day, Masao's luck runs out, leaving them penniless. They continue on foot, facing a series of misfortunes, including an encounter with a pedophile, a stolen taxi, and a desolate bus stop. Along the way, they receive assistance from a hotel manager, a punk couple, and a wandering poet. Upon reaching his mother's home, Masao sees her with her new family. Kikujiro attempts to console the boy, taking him to a fun fair where Kikujiro gets beaten up, and then to a strange beach camp with the poet and two bikers, who are coerced into playing games to entertain Masao. Kikujiro then sets out on his own mission to visit his mother, who is in a nearby home. Eventually, they return to Tokyo and go their separate ways.