Black Cat (TV), Katekyo Hitman Reborn! Recommendations
Both are action-comedies that revolve around hitmen and the mafia.
Reborn has WAY stronger characters, though. Even if it's not as good as the manga.
Both of these series are widely overlook shounen series, and, if we are honest, they tend to blend together. While not specifically about crime families, Black Cat does heavily focus on the criminal underworld and often in a similarly silly way.