The poet Henry Howard, Earl of Surrey

Holbein painted this around 1542, near the end of his own life. He was the king's painter in London and had about a year left. The young man sitting for him had five. Henry Howard, Earl of Surrey, was 25 or so and already the boldest poet in England. With Thomas Wyatt he brought the Italian sonnet into English, and his translation of Virgil gave the language its first blank verse, the unrhymed line Shakespeare would later build on. In January 1547 Howard was beheaded on Tower Hill for treason, the charge turning largely on his decision to quarter the royal arms of Edward the Confessor with his own. Henry VIII died nine days later. The portrait later belonged to the Earl of Arundel in London, who had it engraved, and it has been in São Paulo since 1958.