King Richard III: the earliest surviving portrait.

This is the historical model for Shakespeare's villainous character who claims he can "set the murderous Machiavel to school." in Henry VI, Part 3 (3.2.193). In Shakespeare's play King Henry VI, Part III, the ruthless Richard of Gloucester (later to become King Richard III) claims:

Why, I can smile, and murder whiles I smile,
And cry 'Content' to that which grieves my heart,
And wet my cheeks with artificial tears,
And frame my face to all occasions.
I'll drown more sailors than the mermaid shall;
I'll slay more gazers than the basilisk;
I'll play the orator as well as Nestor,
Deceive more slily than Ulysses could,
And, like a Sinon, take another Troy.
I can add colours to the chameleon,
Change shapes with Proteus for advantages,
And set the murderous Machiavel to school.
Can I do this, and cannot get a crown? (III.ii.182-94)

Painted c. 1520 (approximate date from tree-rings on panel), after a lost original, for the Paston family, now owned by the Society of Antiquaries, London. Picture and data courtesy of the Yorck Project, under Creative Commons Attribution-Share- Alike License (Wikipedia).