Strickland was born into poverty in Cornelia, Georgia, to a black mother and an Irish-Scottish and Cherokee father. Her mother ran a restaurant from their home called Sally's Tea Room, which became a popular spot in the area. However, her family was still poor. She started to draw at an early age, using striped paper from tablets because she did not have access to art paper. As an African American girl in a deeply segregated part of Georgia, she was not encouraged to express herself. She was reprimanded by her teachers when she was caught drawing in school, swatting her with a hickory stick. In 1940, at age 13, Lady Bird moved alone to Harlem in New York to help her sister take care of her five children. Becoming the sole breadwinner for her sister's family, she began work in a zipper factory. She started attending Wadleigh High School for Girls in Harlem, where her artistic talents were recognized and encouraged by her teachers. Her oil painting of a bent-over laundress entitled "The tired woman" was entered into the R. H. Macy's Scholastic Achievements contest by one of her teachers and subsequently won Strickland a scholarship to Pratt Institute, where she was the only female in her soldering class. During World War II, Strickland dropped out of school to find work. Producing paintings to sell, she was noticed by various art critics. Her paintings of the 1940s would reflect scenes of the Harlem nightlife featuring figures such as Josephine Baker, Duke Ellington, Marian Anderson, Eartha Kitt, Miles Davis and Billy Eckstein. She has been photographed by Carl van Vechten, and has done catalogs for Elsa Peretti the jewelry designer for Tiffany's. Later in life, she continued to paint works that reflected social consciousness. Settling in Willingboro, New Jersey, she continued her mission "to paint black history from the heart," and created a number of works featuring significant figures in African American history including Sojourner Truth, Frederick Douglass, W.E.B. DuBois, Jesse Owens, Medgar Evers, and Shirley Chisholm. Her later works also include paintings of former President Barack Obama's election victory.
Personal life
While in Harlem, Strickland entered into an affair with saxophonistJohnny Johnston, resulting in the birth of her daughter Pat Cleveland. She raised her daughter as a single mother in Harlem.