5 American Painters Who Defined the Pirate Mythos

Two Golden Ages

Roughly 150 years after the Golden Age of Piracy, the Golden Age of Illustration began. Advances in technology had made color printing cheaper and easier, and televisions had not yet entered American homes. Howard Pyle, often called the Father of American Illustration, ushered in this Golden Age through his own work and through his Brandywine School—a name given to artists influenced by Pyle’s work and teachings in Pennsylvania’s Brandywine Valley.

Pyle’s exemplary skill as a painter, his meticulous research, and the influence of his teaching reverberate through narrative art today. More specifically, storybook pirates, as defined by Pyle, were repeatedly depicted by the Brandywine artists.

1. Howard Pyle

Along with his dedication to historical accuracy, Pyle was also a storyteller. Understanding how to capture an audience, he created pirates who were an amalgamation of actual pirates and sailors attire, mixed with his own colorful additives.

“Since visual imagery documenting the appearance of early pirates was scant at best, Howard Pyle examined antique prints and manuscripts while perusing his personal archive of historical costume records to create convincingly seductive portrayals of pirates that were drawn largely from his imagination,” writes Stephanie Plunkett, chief curator at the Norman Rockwell Museum. “So lifelike were Pyle’s illustrations that viewers suspended disbelief and accepted with enthusiasm the authenticity and theatricality of his vision.” Plunkett specifically notes the red scarves, stormy backgrounds, and animated expressions in Pyle’s pirate paintings.

In reality, there’s little reason to think pirates dressed much differently from everyday sailors. F. T. Merrill was the first illustrator of Robert Louis Stevenson’s classic pirate story, Treasure Island, in 1884. While those illustrations are full of adventure, it was Pyle who first painted pirates the way we imagine them today in an 1887 issue of Harper’s New Monthly Magazine. For years afterward, Pyle continued both writing about and painting pirates. Ten years after his death, his writing, paintings, and drawings were collected into Howard Pyle’s Book of Pirates.

2. N. C. Wyeth

When Howard Pyle started his school of illustration in 1894, N. C. Wyeth enrolled and became an eager protegé. Within months of beginning his tutelage, Wyeth landed a Saturday Evening Post cover at the age of 21.

In 1911, when Scribner’s sought an illustrator for a rerelease of Treasure Island, they chose Pyle’s young, exemplary student. Wyeth’s Treasure Island paintings retained much of the iconography invented by his mentor. Wyeth also went on to illustrate several Captain Blood pirate-themed books by Italian-American author Rafael Sabatini.

3. Frank Schoonover

Frank Schoonover studied with Howard Pyle at Drexel University, where he sat in class with artists Violet Oakley, Thornton Oakley, Maxfield Parrish, and Jessie Wilcox Smith. When Pyle left to form his own school in Chadd’s Ford, Pennsylvania, Schoonover followed. Over his 60-year career, Schoonover illustrated more than 200 books, including a 1921 edition of Treasure Island, Kidnapped, and Blackbeard Buccaneer.

A brilliant, highly varnished cadmium red, known as “Schoonover red,” became a signature element in many of his works and is unmistakable in his pirate paintings. To fully experience the realism he sought to illustrate, Schoonover traveled extensively. At home, he worked in a Wilmington, Delaware studio just a stone’s throw from Pyle.

4. Dean Cornwell

Though not a direct student of Pyle, Dean Cornwell became an artistic descendant of the Father of American Illustration through his teacher, Harvey Dunn. Cornwell, a prolific commercial illustrator, signed a lucrative $100,000 contract with Cosmopolitan magazine in 1926, equivalent to about $1.8 million today. Cornwell illustrated stories by Somerset Maugham and Ernest Hemingway while working for Cosmopolitan.

A year later, Cornwell sought more lasting recognition for his art. He switched to muralism and was commissioned to paint a large-scale work for the Los Angeles Public Library. He would return to illustration from time to time because he could command top dollar. In 1931 he illustrated Captain Blood Returns, a book perhaps lacking the literary clout of Hemingway but containing as much swashbuckling as can fit in any one book.

5. Norman Rockwell

Best known for nearly 40 years of Saturday Evening Post covers, Norman Rockwell, perhaps more than any other artist, helped define the American Dream. Though not a formal member of Pyle’s Brandywine School, he was heavily influenced by it, as is evidenced by his meticulous research and exacting detail.

A reproduction of Pyle’s Captain Keitt hung in Rockwell’s studio, and his own oeuvre includes several pirates. The red cape, bandana, and peg leg pirate on Thoughts of Home from the June 14, 1924, Saturday Evening Post, certainly harken back to Pyle’s Treasure Island paintings. Still, if there was any doubt, Rockwell spells it out in his painting, Family Tree, with a small “H. P.” inscribed in the treasure chest at the base of the tree.

While these artistic descendants of Pyle carried on his vision of pirates, so did Hollywood. The images created during the Golden Age of Illustration defined the way pirates appeared on screen—from early silent films to Disney’s Pirates of the Caribbean franchise. What we now picture in our minds as a pirate owes much to Howard Pyle and his Brandywine School.