1944 Two letters signed by artist James Montgomery Flagg, with an original caricature self-portrait of the Artist by (James Montgomery Flagg)

Two letters; one typed and signed and the other entirely hand-written; the first on James Montgomery Flagg 340 West 57th Street New York City letterhead and typed, signed in red crayon "Monty", a very amusing and irreverent letter, obviously to a close friend, dated "Indegardampendence Day 1944" (1944 artistically spaced beneath; the addressee 'Paul' from internal evidence was apparently an executive at CBS radio and for whom Flagg worked on occasion), stating in part: "Dear Paul - One of my most favorite characters of fiction and Lousey but Beloved Bastard of Modern Times; Snir; There is a despicable weakness in my otherwise robust ego that lets me write to you on my Model T Corona. I would think my Pride would stop me knowing as I do that you not only will ignore it but in all likelihood wont even read my letter: Maybe you cant read! So you went into advertising. What is this magnetism you use on me? It cant be entirely the hope that I can wangle jobs out of you; And yet what HAVE you got but money? You certainly are not pretty!...(a friend gave Flagg a book on Velasquez)...I pored over it and decided there wasn't such a chasm between Velasquez and me as you would hastily imagine. Except he couldn't illustrated Galsworthy-nor think up Nervy Nat while putting out a pair of clean shorts for Philip IV. You have noticed that Velasquez is NOT listed in Who's Who!..." and more, comparing his talent and lambasting that of Franz Hals, Howard Chandler Christy and Hamilton Fisher; evidently, Flagg was asking about painting a portrait and ends with "...For the love of Mary and Michael Joseph answer this for-free proposal! Don't be a mucous-minded small-town Equine-Brioche!"; the second letter, undated and seemingly from the same period of time and also addressed to "Paul", written in black ink on two sides of plain paper and referring to additional portrait work, Flagg is complaining about bothersome staff and getting paid for his efforts; He jibes Paul with "...Did you get a copy of Owen Wister's "Ancient Grudge"? I told you I'd like to read it on the air- I doubt if you heard me as you were sitting in a dark corner making fond caricatures of me at the time!..." Flagg goes on to speak of other sitters he has had or not been able convince for a portrait painting sitting, mentioning a Mrs. Berwith, Sgnr. Martinelli (most probably Giovanni Martinelli, Italian opera singer) at the Lotos Club and comparing refusals because of 'busyness" to the fact that FDR found the time to have his portrait done; with suitable funny ranting about calling Martinelli a "...shirt with a voice in it!..."; Flagg calls Mrs. Berwith "...she is nothing but a girdle with an angel in it..."; Flagg signs in ink "Monty" with the admonishment below, "Now pay attention to this letter!" and with a wonderful self-portrait caricature in pencil, colored in red crayon and with finger pointing at the sentiment above; letters are perhaps addressed to Paul Kesten, who was Vice President of the fledgling CBS Radio network at this time, during the WWII years; James Montgomery Flagg (1877-1960) American illustrator, cartoonist, perhaps most famously remembered for his fabulous poster art especially of the patriotic variety during the U.S. involvement in wars; typed letter one-sided; script letter is two sided; some edge, tips wear and old lines; some age-darkening; very good condition and wonderful content revealing the humor and personality of this famous American illustrative artist. . Very Good.