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Tim O’Brien

Tim O’Brien

Agwalongdongwas

Tim O’Brien began his oil-on-panel painting with sepia sketches to capture expression, and then carefully refined features before moving to the final image.

Cornplanter

Tim O’Brien transformed preliminary sketches into digital studies to work out color and value before completing this portrait in oil.

Elizabeth Freeman

Working with limited historical reference, Tim O’Brien used sepia sketches and digital studies to help him refine Freeman’s expression before completing the final oil-on-panel painting.

John Jay

Tim O’Brien refined Jay’s expression with sepia sketches and digital studies before completing the final oil-on-panel painting.

George Washington

Before completing the final oil-on-panel painting, Tim O’Brien began with sepia sketches and digital studies to refine expression, color, and value.

From his Brooklyn studio, Tim O’Brien brings decades of experience and meticulous skill to portraits that capture the complexity of historical figures. A native of New Haven, Connecticut, he earned a BFA from Paier College of Art and has illustrated for TIME, Esquire, GQ, Der Spiegel, Rolling Stone, National Geographic, and Playboy, as well as book publishers including HarperCollins, Penguin, Scholastic, and Simon & Schuster. The 2009 Hamilton King Award recipient and current president of the Society of Illustrators has also taught at Pratt Institute and received an honorary doctorate from Lyme Academy of Fine Art.

“Working on this project,” O’Brien reflects, “I discovered just how messy and complicated the formation of the United States was, and how people from all walks of life shaped its story. Bringing these figures to life has been thrilling.”

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Figures of the American Revolution

Meet 25 individuals who played pivotal roles during the American Revolution. Listen to their stories, explore their actions, and encounter the artists who painted their portraits in this commemorative stamp issuance.