The artist is presumably one of those illustrators or caricaturists who made a good living filling magazines and club walls with portraits of the stars of the day. Drawn in 1941 while the sitter was serving as a Lieutenant in the Royal Navy it has all the late Deco style of Hollywood studio portraits of the previous decades.
The subject is the English character actor John Barron (1920-2004) depicted at the tender age of 21 so perhaps it was a present. He found a new generation of admirers in the 1970s, through his role in the BBC TV Series The Fall and Rise of Reginald Perrin. As Leonard Rossiter’s boss CJ, he made the line “I didn’t get where I am today by . . .” a catch phrase repeated by men of a certain generation over and again, up and down the country. Pure nostalgia.