Orochimaru. Seriously he even gets the woman if he burns their village down. Filler or not, you got to have Triple A game to pull that off.
Also, in contrast to Itachi (or some other pretty boy) you will actually be able to discuss useful tactics with him and get awesome feedback. Heck maybe he will learn you some genjutsu to cheat your way through.
With Itachi and Sasuke as wings, they will always go "...." when you try to talk to them. Kakashi would be like "Whatever I'm reading/Gotta train Sasuke/Disappears cause he is lost at the road of life". Shikamaru would find it too much of a drag to help you out.
Johannes Brahms - 'Without craftsmanship, inspiration is a mere reed shaken in the wind'
Juge or Suigetsu. Hell, Jugo and Suigetsu. I'd be all like "Ladies, let me introduce you to my bros, the guy capable of manipulating the size and shapes of various extremities, and the guy capable of triple sizing one extremity at a time."