Jirocho Sangokushi: Koshujij Nagurikomi (1965)
This movie is about the real-life Yakuza boss, Shimizu Jirocho (Koji Tsuruta). His humble beginnings in the Yakuza biz. Jirocho is a likable character, but is also good with a Samurai sword, and is smart too. Jirocho is able to survive competing Yakuza as well as the changing fortunes of the Samurai class. Jirocho becomes a successful business man.
The movie starts out with him as a traveling gambler. He meets up with all kinds of other characters who want to join up with him. The movie is filled with action, drama, comedy, and even some singing.