Rockwell is most famous for the cover illustrations of everyday life he created for The Saturday Evening Post magazine over nearly five decades.

[4] Illustrations for booklets, catalogs, posters (particularly movie promotions), sheet music, stamps, playing cards, and murals (including "Yankee Doodle Dandy"[5] and "God Bless the Hills", which was completed in 1936 for the Nassau Inn in Princeton, New Jersey) rounded out Rockwell's oeuvre as an illustrator.

[6] Many of his works appear overly sweet in the opinion of modern critics,[7] especially The Saturday Evening Post covers, which tend toward idealistic or sentimentalized portrayals of American life.

[9] In his later years, Rockwell began receiving more attention as a painter when he chose more serious subjects such as the series on racism for Look magazine.

The painting depicts Ruby Bridges, flanked by white federal marshals, walking to school past a wall defaced by racist graffiti.

[18][19] Jarvis Sr. was the manager of the New York office of a Philadelphia textile firm, George Wood, Sons & Company, where he spent his entire career.

[25] His first major artistic job came at age 18, illustrating Carl H. Claudy's book Tell Me Why: Stories about Mother Nature.

He followed that success with Circus Barker and Strongman (published on June 3), Gramps at the Plate (August 5), Redhead Loves Hatty Perkins (September 16), People in a Theatre Balcony (October 14), and Man Playing Santa (December 9).

His Sharp Harmony appeared on the cover of the issue dated September 26, 1936; it depicts a barber and three clients, enjoying an a cappella song.

[32] In 1943, during World War II, Rockwell painted the Four Freedoms series, which was completed in seven months and resulted in him losing fifteen pounds.

The United States Department of the Treasury later promoted war bonds by exhibiting the originals in sixteen cities.

King Features Syndicate is reported to have promised a $1,000 per week deal, knowing that a Capp–Rockwell collaboration would gain strong public interest.

The project was ultimately aborted, however, as it turned out that Rockwell, known for his perfectionism as an artist, could not deliver material so quickly as would be required of him for a daily comic strip.

[36] During the late 1940s, Norman Rockwell spent the winter months as artist-in-residence at Otis College of Art and Design.

[37] In 1949, Rockwell donated an original Post cover, April Fool, to be raffled off in a library fund raiser.

In 1959, after his wife Mary died suddenly from a heart attack,[38] Rockwell took time off from his work to grieve.

He spent the next 10 years painting for Look magazine, where his work depicted his interests in civil rights, poverty, and space exploration.

For "vivid and affectionate portraits of our country", Rockwell was awarded the Presidential Medal of Freedom, the United States of America's highest civilian honor, in 1977 by President Gerald Ford.

[46] Irene was Rockwell's model in Mother Tucking Children into Bed, published on the cover of The Literary Digest on January 19, 1921.

[54] Rockwell married his third wife, retired Milton Academy English teacher, Mary Leete "Mollie" Punderson (1896–1985), on October 25, 1961.

Directly underneath Rockwell's studio was, for a time in 1966, the Back Room Rest, better known as the famous "Alice's Restaurant".

[56] From 1961 until his death, Rockwell was a member of the Monday Evening Club, a men's literary group based in Pittsfield, Massachusetts.

[62] The 2013 sale of Saying Grace for $46 million (including buyer's premium) established a new record price for Rockwell.