In 1916, Rockwell married Irene O'Connor and painted his first cover for The Saturday Evening Post, marking the start of a 47-year relationship. Over time, he produced 321 covers for the magazine, including iconic depictions like Charles Lindbergh's flight and Neil Armstrong's moon landing. Rockwell's work captured everyday American life with warmth and humor, though he also addressed social issues, notably in his Four Freedoms series during World War II.
After relocating to Stockbridge, Massachusetts, Rockwell continued painting for Look magazine, focusing on social themes. His acclaimed piece, "The Problem We All Live With," depicted Ruby Bridges' school integration, gaining both acclaim and criticism. Rockwell's legacy endures through the Norman Rockwell Museum, preserving his contribution to American art. He passed away on November 8, 1978, leaving behind a rich artistic heritage recognized with the Presidential Medal of Freedom in 1977.