Norman Rockwell was born on February 3, 1894, in New York City to Jarvis Waring and Ann Mary Rockwell.

He had one brother, Jarvis Rockwell. Norman transferred from high school to the Chase Art School at the age of 14. He then went on to the National Academy of Design and finally to the Art Students League. There, he was taught by Thomas Fogarty, George Bridgman, and Frank Vincent Dumond; his early works were produced for St. Nicholas Magazine, the Boy Scouts of America (BSA) publication Boys' Life and other juvenile publications. Joseph Csatari carried on his legacy and style for the BSA.

As a student, Rockwell was given smaller, less important jobs. His first major breakthrough came in 1912 at age eighteen with his first book illustration for Carl H. Claudy's Tell Me Why: Stories about Mother Nature.

In 1913, the nineteen-year old Rockwell became the art editor for Boys' Life, published by the Boy Scouts of America, a post he held for three years (1913–1916).[1] As part of that position, he painted several covers, beginning with his first published magazine cover, Scout at Ship's Wheel, appearing on the Boys' Life September 1913 edition.

During the First World War, he tried to enlist into the U.S. Navy but was refused entry because, at 6 feet (1.83 m) tall and 140 pounds (64 kg), he was eight pounds underweight. To compensate, he spent one night gorging himself on bananas, liquids and donuts, and weighed enough to enlist the next day. However, he was given the role of a military artist and did not see any action during his tour of duty.

Rockwell's family moved to New Rochelle, New York at age 21 and shared a studio with the cartoonist Clyde Forsythe, who worked for The Saturday Evening Post. With Forsythe's help, he submitted his first successful cover painting to the Post in 1916, Mother's Day Off (published on May 20). 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). Rockwell was published eight times total on the Post cover within the first twelve months. Norman Rockwell published a total of 321 original covers for The Saturday Evening Post over 47 years.

Rockwell's success on the cover of the Post led to covers for other magazines of the day, most notably The Literary Digest, The Country Gentleman, Leslie's Weekly, Judge, Peoples Popular Monthly and Life Magazine.

Rockwell married his first wife, Irene O'Connor, in 1916. Irene was Rockwell's model in Mother Tucking Children into Bed, published on the cover of The Literary Digest on January 19, 1921. However, the couple divorced in 1930. He quickly married schoolteacher Mary Barstow, with whom he had three children: Jarvis Waring, Thomas Rhodes and Peter Barstow. The family lived in New Rochelle, New York. Rockwell and his wife were not very religious, although they were members of ‎St. John's Wilmot Church, an Episcopalian church near their home, and had their sons baptized there as well. Rockwell moved to Arlington, Vermont in 1939 where his work began to reflect small-town life. In 1953, the Rockwell family moved to Stockbridge, Massachusetts. Six years later, Mary Barstow Rockwell died unexpectedly. In 1961, Rockwell married Molly Punderson, a retired teacher.

In 1943, during the Second World War, Rockwell painted the Four Freedoms series, which was completed in seven months and resulted in his losing 15 pounds. The series was inspired by a speech by Franklin D. Roosevelt, in which he described four principles for universal rights: Freedom from Want, Freedom of Speech, Freedom to Worship, and Freedom from Fear. The paintings were published in 1943 by The Saturday Evening Post. The U.S. Treasury Department later promoted war bonds by exhibiting the originals in 16 cities. Rockwell himself considered "Freedom of Speech" to be the best of the four. That same year a fire in his studio destroyed numerous original paintings, costumes, and props.

During the late 1940s, Norman Rockwell spent the winter months as artist-in-residence at Otis College of Art and Design. Students occasionally were models for his Saturday Evening Post covers. In 1949, Rockwell donated an original Post cover, "April Fool," to be raffled off in a library fund raiser.

Later, in 1958, his wife Mary died unexpectedly, and Rockwell took time off from his work to grieve. It was during this break that he and his son Thomas produced his autobiography, My Adventures as an Illustrator, which was published in 1960. The Post printed excerpts from this book in eight consecutive issues, the first containing Rockwell's famous Triple Self-Portrait.

Rockwell married his fourth wife, retired Milton Academy English teacher, Molly Punderson, in 1961. His last painting for the Post was published in 1963, marking the end of a publishing relationship that had included 322 cover paintings. He spent the next 10 years painting for Look magazine, where his work depicted his interests in civil rights, poverty and space exploration.

During his long career, he was commissioned to paint the portraits for Presidents Eisenhower, Kennedy, Johnson, and Nixon, as well as those of foreign figures, including Gamal Abdel Nasser and Jawaharlal Nehru. One of his last works was a portrait of legendary singer Judy Garland in 1969.

Norman Rockwell died November 8, 1978 of emphysema at age 84 in Stockbridge, Massachusetts. First Lady Rosalynn Carter attended his funeral.