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This is a vexed question. There are no fully authenticated oil paintings of Shakespeare. The only fully-authenticated portraits of Shakespeare that exist are the Droushout woodcut which appears in the First Folio and the bust in Stratford Church. Both of these were approved by people who knew Shakespeare personally as accurate portraits. The oil painting with the best pedigree is called the Chandos portrait (that's the one where he's wearing an earring); it is almost but not quite authenticated. Then we get into murky waters. Many people with a sixteenth-century portrait of an unknown man on hand like to claim that it is really a portrait of Shakespeare, and offer feeble arguments in support of the claim (e.g. "The painting once belonged to someone who probably knew Shakespeare.") If the portrait didn't look anything like the authenticated portraits they used to touch them up to look more like Shakespeare, but nowadays, since that is too easily detected, they don't bother, and baldly claim that Shakespeare didn't actually look like his portraits. They get away with this because people like to imagine that Shakespeare was a sexy hunk, not the bald man with the wispy beard shown in all the authentic portraits.

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