Lafayette
Man of Artistic Fingers
I appreciate your suggestion and need to think about it. Old Drac may be too dark. You said he was urban does imply he was charismatic.I am going to suggest someone that might cover just be what you are looking for.
Vlad Dracul, Voivode of Wallachia.
He was notorious in his day. Utterly cruel yet urbane. Highly educated. Took on the might of the Ottoman Empire and held his own. Impaled his enemies by the thousand. I reckon he had a dark sense of humour. Betrayed a few times. I think he ticks all your boxes.
These are the characteristics of my villain:
handsome
charismatic
brilliant
liar
blames other except for himself
hot tempered
athletic
great swordsman
drinks too much, but not an alcoholic
womanizer?