In 1963, Tsuboshima became director after directing his first feature film, "Bet on Life at the Moment", which starring and . He also directed films such as "", which was Toho's dollar box program at that time. Tsuboshima would work under Kengo Furusawa in many movies. In crazy comedy movies, he directed many works that were a bit different from Furusawa, with a lot of wit and fine gag. Starring space alien entrepreneur in "" (1966), Crazy Cats member dancing in the streets of Las Vegas in "Kureji ogon sakusen" (1967) and other latter projects during his time as a director. His representative works included the absurd comedy "Kiki kaikai ore wa dareda?!" (1969), which was warming up the project.