Two of our favorite covers for The Saturday Evening Post by Joseph Christian Leyendecker and George Hughes celebrate the special bonds between mother and son that occur during milestone moments of transition from childhood into adulthood. We take this opportunity to do a deeper dive on the creation of the paintings and the lives of the artist models.

Joseph Christian Leyendecker painted the sentimental image of First Long Suit for the September 18, 1937 issue of The Saturday Evening Post. A fashionable mother dabs away tears as she watches her young son gaze proudly into the mirror as his tailor fits him for his first suit. It’s a moment that signals the boy’s transition into adulthood, which Leyendecker emphasizes by placing the boy on a pedestal and rendering him from a low vantage point to emphasize his stature. The rich colors and textures of the fabrics are applied with Leyendecker’s signature cross-hatching technique, resulting in an engaging visual delight that also tugs at the heartstrings of the viewer. Executed only six years before his final cover for the Post, the painting is representative of a mature artist working in his prime.

Joseph Christian Leyendecker. First Long Suit. Original cover for The Saturday Evening Post, published September 18, 1937. Asking $855,000

The image reflects a proud moment shared between mother and son, but the familial dynamics of Richard Wyndham Hoffmann, the young man who modeled for the painting, were complex. J.C. Leyendecker first painted Richard Wyndham Hoffmann in 1923, when the artist captured the two-year-old boy’s sense of quiet wonder as he perched on Santa’s lap for the December 22 cover of The Saturday Evening Post. But childhood innocence soon darkened for Richard. The following year, his world became consumed by the highly publicized and acrimonious divorce of his parents, the celebrity psychiatrist Dr. Richard Wyndham Hoffmann Sr. and the career-driven actress Janet Beecher. Beecher held unconventional spiritual beliefs that led her to convincing her husband to make a disastrous “spirit-guided” investment in her new play – a move that plunged the family into financial ruin.

Years later, after witnessing the boy’s parental struggles playing out in the press, Leyendecker contacted Richard, now 16, and gifted him the original 1923 Santa cover painting, which the artist personally inscribed. At this time, Leyendecker also asked Richard to model for First Long Suit. The artist saw in Richard a resilience beyond his years, capturing a sense of pride and optimism associated with the boy’s transition into manhood. This newfound maturity soon translated into action. As World War II erupted, Richard, at age twenty, joined the Army Air Corps and became a decorated bombardier, completing 26 daring missions.

Richard married before going off to war, but it did not last. His second wife, “Cookie” Warren, was the daughter of the songwriter Harry Warren, who wrote the popular songs “Jeepers Creepers” and “Chattanooga Choo-Choo.” Richard died in 1959 at the young age of 37. (Reference: “The Art of the Post: The Little Boy on Santa’s Lap” by David Apatoff, The Saturday Evening Post online, December 13, 2023.)

George Hughes. Readying For First Date. Original cover for The Saturday Evening Post, published October 16, 1948. Asking $295,000

In Readying For First Date, George Hughes also uses clothing to mark the moment of a boy’s transition into adulthood as his mother helps him dress in a new Tuxedo before a school dance. We can imagine that the mother and son recently returned from the shop where they picked out his new outfit together, as Hughes includes the realistic details of the discarded boxes and tissue that now lay about the room. While mom may have had a tearful moment in the store, she sets aside that sentimentality to focus on helping her son look his best for the date.

Painted for the cover of the October 16, 1948 issue of The Saturday Evening Post, the work reflects Hughes’ signature wit, as well as a strong attention to detail. The artist reminds us that this is still the bedroom of a young boy through the inclusion of objects like a globe, award ribbons, and a sign warning sign on the entry door. But Hughes didn’t have to stretch his imagination too far in the rendering of the scene, which is situated in the real life bedroom of the boy in Arlington, Vermont. George Hughes used his neighbors, the Rockwells, as models. The young man is Thomas Rockwell, the son of famed Norman Rockwell, and the mother is modeled after Thomas’ actual mother and Norman’s then-wife, Mary Rockwell. According to the Post editors in their description of the painting, Hughes impressed with the cleanliness of the bedroom. “He thought it remarkably tidy, as boys’ rooms go. Temporarily tidy, at least, and you can’t ask more than that.” (Reference: The Saturday Evening Post, October 16, 1948, p. 3)