Cruel Story of Youth
青春残酷物語 (original)
A budding gangster enthralls a freeloading young woman, soon taking advantage of her knack for hitch-hiking to rob middle-class, middle-aged men.
Starring Yūsuke Kawazu, Miyuki Kuwano, Yoshiko Kuga, Fumio Watanabe, Shinji Tanaka, Yosuke Hayashi, Toshiko Kobayashi, Jun Hamamura, Yuki Tominaga, Kei Satō
Watch "Cruel Story of Youth" on Criterion Channel released in 1960. It's a crime and drama movie, and has a rating of 7 out of 10 from Imdb which is usually fine for this kind of movie.