Series: Cowboy Bebop
Notes: Not the typical "bishie", but he does have a certain sexiness about him, not unlike Saitou of Rurouni Kenshin. (They do look alike, don't they?) Vicious and Spike were once partners in the Red Dragon Mafia, but a mysterious woman named Julia shattered their friendship... Spike left the group, but Vicious did not. At the time of the anime, Vicious is plotting to take over as the leader of this crime group. He harbors a hatred for Spike and seeks to kill him several times.
I think the fact that he wields a sword rather than a gun, like most of the characters in this show, is what sold me on him ^_^;