When you think of the works of Andrew Wyeth, what comes to mind? His starkly beautiful paintings of the fields and farmhouses, coasts and rivers of Maine? His portraits of men, women, children and animals? Or, perhaps, “Christina’s World,” the haunting, Maine-set painting that’s undoubtedly his most famous work.

It’s unlikely that you think of Wyeth’s 1981 surreal self-portrait, “Dr. Syn,” — you may not have even seen it at all. In all of Wyeth’s more than 70-year career, there’s hardly another painting like it — in essence, a skeleton, dressed in an early 19th century naval jacket, looking out the window of what appears to be captain’s quarters on a ship.

This summer, you can see “Dr. Syn” in person, along with real-life objects depicted in the painting, at the Farnsworth Art Museum in Rockland. “Dr. Syn” is on display through Sept. 10 at the museum, as part of its larger “Andrew Wyeth at 100” series of exhibits, celebrating what would be the painter’s 100th birthday (Wyeth died in 2009 at the age of 91).

Why is “Dr. Syn” such a seemingly odd addition to Wyeth’s body of work? To understand that, you first have to understand who Dr. Syn himself actually is — unusually for Wyeth, Doctor Christopher Syn is a fictional character, from books by Russell Thorndike published between 1915 and 1944, and from a 1937 film. As curator Leith MacDonald, on staff at the Farnsworth’s Wyeth Study Center, said, the character of Doctor Syn is a swashbuckler, an adventurer, a smuggler and a British gentleman scholar turned outlaw pirate.

“He’s a little obscure now, but he was popular in the first half of the 20th century. He’s kind of a Robin Hood character. He wore a mask that looked like death. It’s a really wild and weird and complicated story,” said MacDonald. “Andrew Wyeth saw a movie about him when he was 20 years old, and it apparently stuck with him.”

Though Andrew Wyeth’s father, N.C. Wyeth, is most famous for his illustrations of classic books like “Treasure Island” and “Robinson Crusoe,” he never illustrated anything from the “Doctor Syn” books. He did, however, own a naval captain’s jacket that dates from the War of 1812, which he used for his studies of the character Horatio Hornblower, based in part on the real-life British naval hero Admiral Lord Nelson.

N.C. Wyeth gave that jacket to his son, Andrew, who kept it for decades after his father’s sudden death in a car crash in 1945. By the time “Dr. Syn” was painted in 1981, Andrew Wyeth was the same age his father was when he died, and mortality was on his mind.

Though the resulting painting is realist in nature, and is executed in Wyeth’s preferred medium, egg tempera, it is at once far stranger than most of his other paintings, with each element of the painting imbued with a dark symbolism.

“‘Dr. Syn’ comes when the artist is a mature person, very different from the artist that painted ‘Christina’s World’ 30 years earlier,” said MacDonald. “He’s looking back at his entire life and grappling with it. ‘Did I peak at age 30?’ There’s a lot of symbolism in this painting about his own upbringing, and it’s especially notable that the bones in the painting are his own bones, painted from his own X-ray. It’s a very serious painting.”

Wyeth set his dark, surreal self-portrait in the odd little out building on Southern Island, the 22-acre island just off Tenants Harbor that Andrew’s wife Betsy purchased in 1978. Betsy refurbished the building to meticulously replicate Admiral Lord Nelson’s actual captain’s quarters, from the black and white floors to the curved beams.

“I don’t know how she did it, but she got all these exacting details, and retrofitted this existing, simple structure into this incredible replication. She gave it to Andrew as a gift, to use as a studio,” said MacDonald. “‘Dr. Syn’ is his reciprocal gift back to her on her 60th birthday, though that name is never a name he gave to it. Betsy called it ‘Dr. Syn.’ The tag on it read, ‘To the Queen of Southern Island, from Old Bones.’”

Years later, Andrew Wyeth gave his son, the acclaimed painter Jamie Wyeth, the captain’s jacket. It has since showed up in several of Jamie Wyeth’s paintings, including “Meteor Shower” and “Lighthouse Study with Sea.”

Between N.C., Andrew and Jamie, the jacket has appeared in multiple paintings over the course of nearly a century, from three generations of artists. All three of the jacket paintings are connected in some way, be it N.C. Wyeth’s depictions of Horatio Hornblower, Andrew Wyeth’s meditation on mortality in “Dr. Syn,” set in his wife’s real-life recreation of Admiral Lord Nelson’s captain’s quarters, or Jamie Wyeth’s hanging of the jacket on a scarecrow, a kind of echo of his father’s putting it on a skeleton.

“It says so much about all of them,’” said MacDonald. “It’s an unbroken connection.”

“Dr. Syn” hangs at the Farnsworth alongside the famous jacket, of course, as well as the cannon pictured in the painting and preparatory drawings and watercolors that led to the final painting. The “Dr. Syn” exhibit is part of the larger “Andrew Wyeth At 100” exhibit, which also includes “Maine Drawings” and “Maine Watercolors, 1938 to 2008.” In total, more than 100 works by Andrew Wyeth are on display through the summer at the Farnsworth.

Leith MacDonald will give a talk about “Dr. Syn” at 1 p.m. on Friday, Sept. 1 at the Farnsworth. For more information, visit farnsworthmuseum.org.

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Emily Burnham

Emily Burnham is a Maine native and proud Bangorian, covering business, the arts, restaurants and the culture and history of the Bangor region.