All six are on 8.5x11” sheets c. 1938-1940. Art is pencil and watercolor titled “Nonchalance- Cutie Making Up Her Mouth” signed in pencil at lower right “J.M.F.”. Four letters are handwritten, one in pencil, three in ink. One is typewritten. All are to his art agent Maggie Humphries, written on two sides. Three are addressed to “Maggie”. Contents include wanting $250 for movie star caricatures, wanting to do work more current than his 1890’s style, “My Crack of the Week Was Asking Rube Goldberg if He Had A ‘Christian Front””, Humphries choice of models. Two letters are signed “Jimmy”, three are signed “Monty”. All six items have lt. creases as mailed, overall Fine/VF. Comes w/four unsigned ink note pages from agent explaining her problems w/ad man alcoholic husband, and falling out w/Flagg. Pages are aged. VG. Fascinating personal archive regarding the noted illustrator, famous for his WWI Uncle Sam “I Want You” poster. From the Charlie Roberts Collection.