Portraits of a Lady follows the quest of 25 artists to illustrate the same subject, at the same time, and in the same place. Normally such an assignment would be nothing more than a curiosity, but in this case, the subject is U.S. Supreme Court Justice Sandra Day O' Connor, a true pioneer who became the first woman appointed to the U.S. Supreme Court. Director Neil Leifer captures the different points of views of the Painting Group, a group of artists who meet weekly in New York City to paint portraits. On this occasion, each will create their own interpretation of the venerable Justice. While O' Connor poses, she provides her audience of painters with intriguing and humorous anecdotes about the history of the Supreme Court. Throughout the film, the artists and the founders of the Painting Group, Aaron Shikler and David Levine, are interviewed to gain a keener insight on their perspectives and experience painting portraits. While providing instruction and feedback to their fellow painters, Shikler and Levine often contradict each other to humorous effect. The film, which concludes as the 25 completed portraits are unveiled at the National Portrait Gallery, is an enlightening commentary on perspective, both artistically and politically.

In 1981, President Ronald Reagan nominated Sandra Day O'Connor to the Supreme Court, making her the first female Justice in U.S. history. O'Connor served as Associate Justice for 24 years before her retirement in 2005. During her tenure, she often cast decisive swing votes on issues that divided the court, in part because she approached each issue on a case-by-case basis, maintaining a more moderate stance than some of her counterparts. Though she hoped to stay on the bench, O'Connor made the decision to step down in order to care for her ailing husband. With a wry sense of humor and a vast knowledge of judicial history, it is easy to see how Justice O'Connor has inspired the women of her generation, paving the way for other female Justices to come.

Featured in this film are artists Aaron Shikler and David Levine, founders of the Painting Group, which has been meeting in New York for over 50 years. Shikler is well- known for his portraits of prominent American politicians. He painted the postmortem White House portrait of President John F. Kennedy, as well as the official White House portraits of First Ladies Jacqueline Kennedy and Nancy Reagan. Levine, painter, illustrator and caricaturist, is famous for his caricatures of world figures in politics, published in The New York Review of Books as well as many other publications. Both artists' works are part of collections in major museums around the world, including the Metropolitan Museum of Art in NY, the Smithsonian Institution's National Portrait Gallery in Washington, D.C., and many others.

The 25 painters of the Painting Group each chose to capture Justice O'Connor in their own distinct ways, some concentrating on intricate details like the lacework on her collar, others trying to catch the sparkle of humor in her eyes. The resulting works were vastly different. David Levine created a raucous caricature; Aaron Shikler focused on recreating O'Connor's well-known white collar; another artist chose to superimpose a real piece of lace onto a painting, giving it a more three-dimensional view; others, like Gil Eisner, added a scenic backdrop to take her out of the room.

ABOUT THE FILMMAKERS: Portraits of a Lady is produced and directed by Neil Leifer, noted Sports Illustrated and Time Magazine photographer, and executive produced by David Hume Kennerly, the award-winning photojournalist. In 1972, Kennerly won the Pulitzer Prize for feature photography, and served as the official White House photographer under President Gerald Ford.

CREDITS: Directed by Neil Leifer; Produced by Walter Bernard and Neil Leifer; Executive Produced by David Hume Kennerly; Director of Photography: Peter Franchella; Editor: Jonathan Wendell; Music by Brian Keane. For HBO: Supervising Producer: John Hoffman; Executive Producer: Sheila Nevins.

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