Dude's a hard worker, instead of camping in his lair like all the other bosses, waiting for someone to show up, he actually tracks Dante down right off the gate, and then when defeated has the integrity to climbs all the way to the top of the evil tower to report back to his boss, knowing full well he's not going to get a raise. Virgil did done a massive blunder by axing him off (HV still cool - coming back at him with a darth maul dive), not realizing his true potential, cause not only did he ambush Dante, he then actually LIVED to tell the tale. He could have been this assassin personification of death that followed the player everywhere and attacked at most inopportune times, even hijack some other boss fights (denedent on chosen difficulty level I guess) and be a general manace. There is even another one you encounter later, so there could be a whole pack of em hunting you, but alas never given the time to shine as every other poor hard working hobo with nothing to their name.
He's got the coolest scarface and gloweye, the coolest dark hobo rags, the coolest scythe, the coolest shadow teleport effect, the coolest banshee wail, the coolest hyena chuckle and the absolute coolest church bells of death attack sound effect.