A lifelong resident of Chestnut Hill, Lear played at Woodmere in his childhood; from boyhood through life he remained the friend of the son of the Museum’s founder, Charles Knox Smith. He attended Chestnut Hill Academy (now Springside Chestnut Hill Academy) and the Pennsylvania Museum and School of Industrial Art (now the University of the Arts). During World War II, Lear’s drawing abilities caught the attention of high-ranking officials at Fort Riley, Kansas, where he made portraits of generals and officers. He also illustrated military manuals, books, and charts. Lear taught illustration at Rosemont College and was an instructor at the Hussian School of Art and Philadelphia College of Art (now the University of the Arts). His works are in the collections of the Philadelphia Museum of Art, Woodmere Art Museum, the Detroit Institute of Arts, the Reading Public Museum, as well as other institutions in Canada and Mexico.