- Rockwell enrolled in classes at the New York School of Art when he was 14. After high school, he studied art at The National Academy of Design and The Art Students League.
- While he was still a teenager, Boys Life magazine hired Rockwell as art director. He also began working as a freelance illustrator for other publications.
- Rockwell moved to New Rochelle, New York, at the age of 21 and established a studio with cartoonist Clyde Forsythe. At this new studio, Rockwell produced work for Life, Literary Digest and Country Gentleman magazines.
- In 1916, Rockwell produced his first cover illustration for the Saturday Evening Post. Rockwell considered this publication to be "the greatest show window in America," according to Normanrockwellmuseum.org.
- The 1930s and 1940s were considered to be the "most fruitful decades" for Rockwell, according to Normanrockwellmuseum.org. During this time, Rockwell produced his famous "Four Freedoms" paintings.









