The March 2, 1963, cover was of comedian Jack Benny at the ripe old age of (what else?) 39. Rockwell later noted that he was tempted to ask the famous “miser” if he really kept his money in a basement vault.

Rockwell illustrated for other publications as well, such as Country Gentleman magazine, owned by the same publisher as the Post. This magazine’s Summer 1976 issue boasted a Rockwell portrait of John Wayne, whose “rocklike visage challenges the great faces on Mt. Rushmore,” according to the editors, who added, “but he gets around more.”

The May 24, 1930, cover is not exactly a portrait, but the cowboy the makeup artist is working on is none other than Gary Cooper. “He posed for me in Hollywood for three days and worked as conscientiously as any model I ever had,” Rockwell said, “everybody at the lot was crazy about him, and I could see why.”

The fun and mischievous personality of Bob Hope shines through in the February 13, 1954 cover. Hard to believe Hope agreed to pose the very day he returned from a trip to Europe. Most of us would look drained and dull-eyed after an exhausting journey. Can’t you just hear him quipping, “I just flew in from Europe and boy, are my arms tired!”

Rockwell in Hollywood The Saturday Evening Post