Cloar was raised on a cotton farm in Arkansas, and was inspired to pursue an art career in high school. In 1931 Cloar moved to Memphis, Tennessee and studied English and Spanish at Southwestern University. He also took a few courses at the Memphis Academy of Art. Soon after graduating from Southwestern, Cloar moved to New York City to become an illustrator and cartoonist. In 1936 he began studying part time at the Art Students League where he was heavily influenced by his instructors, Arnold Blanch and William McNulty. He eventually grew tired of the city and traveled through the Southwestern United States and Mexico. During this time he continued to produce work inspired by rural life in Arkansas. His style combined realism and naïveté with people and places from his childhood memories. His work belongs to many important museum collections including: the Metropolitan Museum of Art, New York; the Whitney Museum of American Art, New York; the Museum of Fine Arts, Boston; the Hirshorn Museum and Sculpture Garden, Washington D.C.; Arkansas Arts Center, Little Rock; and Crystal Bridges Museum of American Art, Bentonville, AR.