Academy Alum Paints Oprah Winfrey Portrait for Smithsonian Collection

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Recently, the Smithsonian’s National Portrait Gallery unveiled a new portrait of Oprah Winfrey painted by Chicago-based artist and Academy alumnus, Shawn Michael Warren. The portrait will be included in the museum’s permanent collection as part of a continued effort to feature portraits of influential living figures who have significantly impacted American history and culture.

“Until We Meet Again:” The Oprah Winfrey Mural Artist: Shawn Michael Warren

Warren was chosen for the commission after his involvement in a mural project featuring Winfrey in Chicago’s West Loop, prominently displayed on the side

of an apartment building along Green Street. The mural served as a tribute to the nearby former Harpo Studios campus, the production site of the Oprah Winfrey Show from 1990 to 2011.

While painting at night to avoid the daytime crowds, Warren met a former Harpo staff member who told Oprah about the mural. When Warren shared the completed mural on his Instagram in 2020, Oprah commented, “Wow! How’d you do that??!” And for this to be in my old neighborhood only a few blocks from Harpo Studios. Thank you for the honor. Looks like, more importantly, feels like me.”

A critic of his own work, Warren described his process by saying, “The drawing is the most important. If the drawing is incorrect, the painting is not going to do well. The drawing is the bare bones. I am a very avid believer and practitioner of drawing. Having the fundamentals of drawing down pat for a portrait is essential, and I would encourage any artist always to draw.”

Oprah Winfrey and Shawn Michael Warren at the portrait unveiling ceremony at the Smithsonian’s National Portrait Gallery on December 13, 2023 in Washington, DC. Photo: © Tony Powell.

The full-length, oil on linen portrait is approximately 6 feet, 10 inches tall and is described on the National Portrait Gallery’s museum label:

Wearing a purple taffeta gown to symbolize the significance of Alice Walker’s novel The Color Purple (1982) in her life, Winfrey is portrayed surrounded by twelve interwoven oak trees. Being a woman of strong faith, she likens them to the twelve disciples. The Chicago-based artist Shawn Michael Warren grew up watching and admiring Winfrey on television. In showing her smiling and extending an olive branch, he conveys Winfrey’s elegant, playful, warm, and generous spirit.

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