He began to work as a freelance copywriter in 1987, and in his free time, wrote the novels that would give him his cult following in Japan, as well as a variety of rakugo, essays, scripts and short stories.
After his success in novels, he then expanded into theater, producing Laugh-to-Death Lilliput Army, as well as creating his own rock band, PISS, of which he was the lead singer and guitar player.
After the band dissolved, he then formed Ramo and the Mother's Boys, where he played rhythm guitar and sang.
His appearances on television in the late 1990s and early 2000s were always an audience draw because of his slurred speech—probably from years of alcohol and drug abuse—and humorous personality.
On July 15, 2004, after drinking late at a bar, he fell down a staircase and suffered serious head injuries.