Norman Rockwell's first sketches were drawings of warships from the Spanish-American war. He studied at the Chase School of Fine and Applied Art and after his sophomore year in the National Academy of Design and the Art Students League in 1910. It was during this time that he bagged his first art job, the designing of four Christmas cards. But it was his illustrations for the children's book 'Tell Me Why Stories' that catapulted him into popularity.

He was soon hired by 'Boy's Life' magazine, the Boy Scouts of America publication, as an art director, for which he illustrated the boy scouts calendar for 50 years. He then set up a studio with cartoonist Clyde Forsythe and started freelancing for magazines such as 'Life', 'Country Gentleman', and 'Literary Digest'. By 1916, he sold his first cover illustration to the then prominent 'The Saturday Evening Post', and it proved to be a sell out. Rockwell went on to create 321 typical American life and value portraying covers for the Post. Each of his covers were well received and highly acclaimed to such an extent that the post sold an additional 50,000 to 75,000 copies thanks to Rockwell's covers.

He also illustrated for new editions of the classics 'The Adventures of Huckleberry Finn' and 'Tom Sawyer.' His most patriotic work came during World War II, when he painted the 'Four Freedoms', which were published on four consecutive days and raised $139.9 million in aid of the war. After quitting the Post, Rockwell started working with 'Look' magazine; it was during this tenure that he sketched some of his most astoundingly hard hitting images. Taking inspiration from issues of civil rights and poverty, Norman managed to throw light on problems that most Americans had earlier ignored. He was awarded the country's highest civilian honor, the Presidential Medal of Freedom by President Gerald R. Ford in 1977. He was once quoted as saying 'Without thinking too much about it in specific terms, I was showing the America I knew and observed, to others who might not have noticed.'