I love how we all see Vergil as being the pinnacle of cool, probably even cooler than Dante, when-- if you think about it-- Vergil has lost every single time.
He lost to Dante and then fell into the underworld and immediately tried to take on Mundus like an absolute moron. Then he gets turned into Nelo Angelo, only to get beaten again by Dante (THRICE). Then he... wanders around for a bit, probably getting his ass beat again somehow, leading to him going back to the ruined Sparda mansion and severing his demon half from his human half SPECIFICALLY to attain ultimate power, which he eventually SUCCEEDS IN DOING-- the only time I can say that he won (AND IT'S TEMPORARY)-- only to get his ass beat once that happens. And once he loses, his human half has basically realized "dawg I don't think any of this is worth it anymore" and so when V re-fuses with Urizen back into Vergil, Vergil has thusly realized that all of this has basically just been a big waste of time. And so he decides to just give it a rest, should Nero beat him. Which he does.
I guess that just goes to show how much of a difference taking a loss (or several games' worth) with grace makes a difference, huh?