Ann Landers

This 1988 portrait of Ann Landers by Roger Robles hangs in the National Portrait Gallery in Washington, DC.

“Esther Pauline Friedman became the incredibly popular columnist Ann Landers in 1955, when she won a contest to write the syndicated newspaper feature ‘Ask Ann landers.’ Throughout her five-decade career she changed the tone of advice columns from treacly to direct and candid. Her sympathetic guidance reached more than 90 million readers through more than 1,200 newspapers. She counseled people on everything from wedding etiquette and the correct height of toilet paper to more serious topics, including cancer and AIDS. Throughout much of her life she was in direct competition with her twin sister, who wrote her own column, ‘Dear Abby.’

The California artist Roger Robles painted Landers's portrait twice, in 1977 and 1988. Landers preferred this later portrait since it made her look ‘less starchy.’ She displayed the painting in her apartment until her death.” – National Portrait Gallery

 Roger Robles 1988

The Library of Congress has this 1961 New York World-Telegram & Sun staff photo of Ann Landers.