Marge's interest in art is reawakened when she finds some of her old paintings in the attic. Signing up for a painting class taught by Professor Lombardo at Springfield Community College, Marge eventually develops enough confidence in her work to enter the Springfield Art Fair and win. Her winning painting catches the eye of Mr. Burns, who hires her to paint his official portrait, a task that proves very difficult because Marge finds Mr. Burns to be excessively ugly. Eventually, she paints a picture that emphasizes Mr. Burns' flaws. But rather than embarrassing him, the portrait humanizes him in the eyes of the public and he is forced to accept the painting as a success.
Guest star: Jon Lovitz as Professor Lombardo; Ringo Starr as himself.