After Werntz looked at sketches by Richard, he was invited to enter day school. However, he was only fifteen and already had a diversified but tightly scheduled boyhood. He was looking forward to attending high school and playing football and could only consider art school on Saturdays. Before making the decision he wrote to two American Impressionist painters he admired, Edward Redfield and George Gardner Symons, who became known as leaders of the Impressionist clan. Both wrote back giving him encouragement and advice. Unlike his father, Richard did not yearn to be an illustrator or art director. His desire was to pursue the fine arts he had seen in Chicago exhibitions. He and his father spent a great deal of time talking about paintings and artists and attending every exhibit that came to Chicago. One exhibition of Aldro Hibbard at the Carson Pirie Scott & Co. department store stood out in his mind and had enormous impact on his career. The public also appreciated the exhibition, as it sold out in two days. In 1929, the stock market crashed on Wall Street, leading to a worldwide economic depression. The Depression drastically changed the art world and put an abrupt end to the Impressionist movement to make way for a new direction called Modernism. In 1930, Thompson, age 16, entered both Oak Park High School and art school at the Chicago Academy of Fine Arts, attending on Saturdays during the school year and day classes during the summer. Painter Frederick Milton Grant, who was a student of William Merritt Chase, was a mentor to Richard. He was surrounded by members of the Hoosier Group, a group of Impressionist painters who painted the Indiana landscape. He watched Carl Krafft, John Spellman, Jess Hobby, and Charles Dahlgren paint canvas after canvas. Richard often visited Hobby in his Oak Park studio and learned additional painting techniques not taught by Grant. In 1932, Thompson, age 18, entered art school for a two-year term at the American Academy of Art in Chicago. There were 21 instructors and 400 students. The academy had a reputation for training competent illustrators and designers. He was most inspired by two of them – Edmund Kellogg and Frederick Milton Grant. Thompson now saw his future career path temporarily shift to illustrator during the Depression economy. In 1933, after graduating from Oak Park High School, Richard’s first job was with "Esquire" as a commercial artist. At night he was a student of Louis Ritman at the School of the Art Institute of Chicago.