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Understanding and Interpreting
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1. What is your first reaction to Amy Sherald’s portrait of First Lady Michelle Obama? In what
ways does she resemble photographs that have been taken of her? In what ways does she
seem different?
2. How would you characterize Michelle Obama’s expression? Why do you think Sherald
painted her looking directly at the viewer?
3. In an interview published in the New York Times, Sherald said that her subjects “exist in a
place of the past, the present and the future,” adding that “it’s like something I sense more
Redefining America
with my spirit than my mind.” In what ways does this portrait of Michelle Obama seem
simultaneously from the past, in the present, and of the future?

Analyzing Language, Style, and Structure

1. Michelle Obama’s skin color is painted in shades of gray. The technique, a classical one, is
called grisaille, and Amy Sherald uses it for the skin tone of all of her portrait subjects. How
does this choice characterize First Lady Obama? What does it suggest about Sherald’s
relationship to her subject?
2. Consider the proportions of the portrait. How much of the space is taken up by the subject’s
gown? By Mrs. Obama’s head and shoulders? What message might Sherald have intended
by using those proportions?
3. Look carefully at the shape of the main subject, especially in relation to the canvas itself.
Also, look at the shapes in the dress First Lady Obama wears. What do you associate with
these shapes? What do they convey about First Lady Obama?
4. You may have noticed that this painting has a flat background, with no horizon line to anchor
the subject or suggest depth. What effect does this choice have on the painting?
5. Sherald generally paints on very large canvases. This portrait is no exception, measuring
72 1/8 × 60 1/8 inches, or roughly 6 feet by 5 feet. How does the size of this painting
contribute to its effect? What message does it convey to the viewer?

Topics for Composing

1. Analysis. In a 2018 essay in the New Yorker, writer Doreen St. Felix says that “Evidence of
power is more elusive in Sherald’s paintings” than in those of Kehinde Wiley, who painted
Barack Obama’s portrait. Does this painting convey power to you? If not, what does it
convey? Explain your answer.
2. Argument. In a review of this portrait for the New York Times, critic Holland Cotter
commented that “Ms. Sherald’s image of Mrs. Obama overemphasizes an element of
couturial spectacle, but also projects a rock-solid cool.” Write an essay in which you develop
a position on that assessment.
3. Connections. Michelle Obama chose the dress she was painted in, a cotton poplin halter
dress designed by Michelle Smith for Milly. In an article in Vogue magazine, Smith said
that the dress’s “clean, minimal geometric print” is “without reference to anything past or
nostalgic” and is “forward thinking” like Obama herself. Painter Amy Sherald said the shapes
on the dress reminded her of the work of the artist Piet Mondrian (1872–1944) and the
“diligent quilt-making of the black women artist of Gee’s Bend, Alabama.” And, of course, the
halter style shows off Michelle Obama’s well-toned arms, a subject often brought up by the
press during her time as First Lady. Choose a photograph or portrait of a public figure and
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