In my opinion the coolest ninja is (by far) Itachi, not only he beat Orichimaru with ease (the Orichimaru that was in Sasuke that is) but he also pushed Sasuke to the limit to make sure that Orichimaru appears as the last resort; sacrificing his honour and life (*2) for the better good. Envisaging that he can be brought back from the dead and making preparations what to do in this case.
See I disagree here, the whole success of Naruto was that villains were introduced in progression from Orichimaru to Madara, becoming stronger and stronger. Every time when a villain would gain some strength and go from a villain to super villain it somehow came out as less credible (like Kabuto, under the mentoring of Orichimaru btw
)
I think Madara was a perfect villain - dead for centuries, always in a shadow, absolutely stunning looks and ... the last but not least he was not a villain in his own right, he just wanted everyone to be happy...
A few questions for both of you - (my gf and I stopped talking because of this argument, so I want to know your opinion):
1. 3 best looking male characters in Naruto
2. 3 best looking female characters in Naruto
3. Best couple in Naruto/Boruto
4. 3 overall coolest characters