I'll start with Cesare Borgia (above), a violent psychopath whose senseless wars of conquest helped to undermine the Italian Renaissance. Orson Welles played him in a film called "Prince of Foxes" which I highly recommend.
His was an interesting face, no? Some contemprary painters patterend their depictions of Christ on him.
How about Genghis Khan (above)? He waged brutal, senseless war just to enhance his own reputation.
Then there's the mass murderer, Stalin, shown here in the days when he was a young thug.
Here's (above) Ivan the Terrible, a man who was aptly named. He was an evil man but I cut him a little slack because at great cost he stood up to the Mongol invasion and thus bought time for Europe to achieve a new Golden Age.
Then there was Mao, apparently the greatest mass murderer of the 20th Century, stacking up a body count that exceeded even that of Hitler and Stalin. Read about what went on when he tried to enforce his "Great Leap Forward."
By the way, Hitler certainly deserves a high place in this rogues gallery but I left him out because I couldn't find a suitable picture. Every photo of him has already been seen a gazillion times.
Not so frequently seen is this recent reconstruction of the head of Robespierre, architect of the French Revolution's "Reign of Terror." I always pictured him as having a thin, angular face, but I guess I was wrong.