Nobody talks about this one. A man lives two lives that refuse to sit still, underwear designer by morning, yakuza boss by night, and the OVA treats both with equal weight, finding the absurd dignity in existing between worlds. The joke isn't that these lives are contradictory. The joke is that he's competent at both, and that matters to him the same way. 1991 was too early for this premise to find an audience.
Shizuya Kondou is the only son of the man who runs the biggest yakuza syndicate in the Kanto region, but he wants no part of it. Instead he takes a job as a novice designer at an underwear company. When his father is assassinated, Shizuya ends up inheriting the gang. His condition is that he keeps his day job, so he must hide who he really is from his colleagues. Among them is a young woman hoping to become a designer herself. She is the one he cares for, and the only person able to keep his violent side in check. This single-episode 1991 OVA is adapted from Nitta Tatsuo's manga, which ran in Shonen Sunday.