Emmett Kelly clown paintings include Dmitri Vail's full-body portrait entitled "Emmett Kelly" and Barry Leighton-Jones' series of paintings entitled "The Emmett Kelly Collection." Vail's "Emmett Kelly" painting, which he painted in 1959, depicts Kelly in ragged clothing with his classic sad expression. Kelly is standing and starring off into the distance as he holds a cabbage with his left hand and a small piece of a cabbage leaf with his right. He is standing against a vibrant, multi-colored background.
In 1985, the Kelly Estate commissioned Leighton-Jones to create a series of paintings and sketches that represent different aspects and stages of Kelly's experience as a clown. In Leighton-Jones' painting "Emmett, Kelly: Memories," Kelly is leaning against a large wheel with his head propped up by his right hand. His eyes are cast downward in a contemplative way, and his mouth is completely straight. A collage of various images of Kelly's circus life appear in the background, representing the memories that the contemplative Kelly figure is supposedly in the act of recalling.
In another Leighton-Jones' "Emmett Kelly: Guess Who's Coming to Dinner," Kelly is sitting outside of a circus tent, on a crate, roasting sausages over a small open fire. On his right side, a little boy carrying a bundle attached to a stick is looking down at Kelly and the food, and a small circus dog is looking up at Kelly with its paw on Kelly's knee.