Each is 8.5x11” written between 1938 and 1951 to Miss Marjorie Norton, who became Mrs. Douglas Humphries. 16 are typewritten, four are handwritten including one in ink and three in pencil. Most are witty and of a personal nature. Includes “ Are You Sunkist By Now Maggie And Doing Your Hair 100 X? Don’t Forget How To Laugh-That’s A Life Saver!; I Think I Could Count On One Hand The Really Civilized People I Know; I Had Nothing I Cared To Live For-Then Boom- Came Love & The World Was A Better Place; I’m The Feller That Understands Women! Maybe Because I Have Been The No.1 Sucker!; Imagine My Having An Agent- A Female Agent. It’s Fantastic. A Depressing, A Belittling Agent! Oof! Omsk!; The Bloated Bluebottle Flies Are No Doubt Biting You On Your Westbrook Pegler As You Read This!” One is signed “Jimmy”, one is signed “Jim”, the others are signed “Monty”. All have lt. creasing and handling folds as mailed. Overall VG/Fine. Flagg (1877-1960) was one of the top illustrators of the first half of the 20th century, gaining great fame in WWI for his “I Want You” Uncle Sam poster. Great insight into a gifted artist. Comes w/Hake’s COA.