A florist turned artist, Jessie Drew-Bear (born Jessie Henderson in 1877) began her artistic career at 59 when her daughter gave her a paint set for Christmas. As a young woman, Drew-Bear had moved from England to Philadelphia, opening the London Flower Shop on Chestnut Street, and her floral arrangements decorated society galas and debutante balls. After Christmas in 1938, Drew-Bear began to take classes with prominent Philadelphian artist, Arthur B. Carles, and spent a month in Fernand Léger’s atelier in 1949. This was the extent of her formal training.
Primarily self-taught, Drew-Bear's art incorporates a whimsical and fanciful approach, using bright colors and textured surfaces to surrealistically depict personal narratives and fairy tales.
Although she maintained a home and studio in New Hope, Drew-Bear was well-traveled, spending time painting in Greece, Holland, and the French Riviera. During her twenty-three year career, Drew-Bear's work was exhibited in over fifteen solo exhibitions at institutions including, the Pennsylvania Academy of Fine Art, the Newman Contemporary Art Gallery, and the Philadelphia Art Alliance. Her work was also acquired by notable gallery owners and art collectors such as Albert Duveen and Sidney Janis. Several of her works are now housed in the Woodmere Art Museum's collection.