Now Blooms the Tudor Rose/YMMV

• Ensemble Darkhorse: Charles von Hapsburg, Prince of the Asturias, and son of Philip of Spain, has acquired a surprising fanbase, even though he is a side character.
• Iron Woobie: Edward Tudor, Duke of York, is a Renaissance era Emo Teen for a reason...
• Jerkass: Quite a few monarchs qualify, though Henry VIII, Francois I, and Henry II of France probably top the bill.
• Magnificent Bastard: Anne Boleyn, as a Manipulative Bastard and The Chessmaster, obviously also fits this trope. Pope Pius IV also qualifies.