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Ann Pennington was born in Wilmington, Delaware. Her family, who were Quakers, moved to Camden, New Jersey when she was a child. She took dancing lessons from ballerina Catherine Littlefield. At the age of seventeen she made her Broadway debut in the musical. She joined the Ziegfeld Follies in 1913. With her long, red hair and great legs she quickly became one of the show's most popular dancers. Her nickname was "The Girl With The Dimpled Knees." Ann became best friends with fellow dancer Fanny Brice. In 1916 she had a starring role in the silent movie Susie Snowflake. Then she appeared in the films The Rainbow Princess, The Antics of Ann, and Sunshine Nan. After six years with the Follies she left to join George's White's Scandals. She began a romance with the show's producer George White. Ann also dated actor Buster West and boxer Jack Dempsey.

While performing in the Scandals she introduced the Black Bottom Dance to Broadway audiences. She returned to the Ziegfeld Follies in 1923. By this time the petite dancer was earning more than $1000 a week. Off stage she was known for her great wit and her generosity. Her biggest vice was betting at the racetrack. In 1929 she appeared in five films including Tanned Legs and Gold Diggers Of Broadway. During the 1930s her popularity started to wane and she performed in vaudeville. Ann had bit parts in the films Unholy Partners and China Girl. Her final stage appearance was a 1946 benefit show for the Armed Forces. After retiring she moved into a modest New York hotel and stayed out of the spotlight. She turned down most interview requests saying "I'd rather be thought of as the way I used to be." Ann spent most of her time socializing with friends and doing charity work. On November 4, 1971 she died from a stroke at the age of seventy-seven. She was buried at Kensico Cemetery in Valhalla, New York.

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