Reginald Brill studied at the Slade under Henry Tonks from 1921-24 and was subsequently awarded the Prix de Rome in 1927. He travelled to Egypt, Greece and Italy before settling in London where in 1933 he was appointed the Head Master at Kingston School of Art, a post that he was to keep until 1962.
Brill’s subjects in the 1950’s are scenes of everyday English life. The pictures which he exhibited at The Royal Academy demonstrate the artist's appreciation of rural characters and are imbued with an English humour which is reminiscent of Stanley Spencer. It was in Autumn of 1953 that he began to specialise in large figure compositions similar to The Philosopher which included The Dustman, The Window Cleaner, and The Tramp.
During his career at the Kingston School, Brill became actively involved in all aspects of artistic life in Surrey, but above all, he worked relentlessly to help his students.