There aren't a lot of contemporary paintings of pirates - particularly Golden Age ones. I believe there's one painting of Captain William Kidd that survives, but he became infamous a few decades before the Golden Age, and he wasn't much of a pirate anyway. There are 18th century engravings of pirates like Blackbeard, but for me, the most memorable images of pirates came long after the early 18th century - from Howard Pyle.
Pyle was an American writer and illustrator who became well-known in the 1880s. Howard Pyle's Book of Pirates, which included his illustrations was published a decade after his death in 1921. I like his pirate illustrations because they're so colorful, almost whimsical. They're more romantic than realistic. He even did some of Captain Kidd, though they look nothing like him. I've posted Pyle's images of Captain Kidd above, with the contemporary painting in the middle. My favorite Pyle illustration is the Marooned Pirate, which is posted below, at the very bottom.
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