FROM THE PAGES OF COMIC BOOKS TO THE WALLS OF THE WHITE HOUSE, KINSTLER’S EXTRAORDINARY CAREER MADE HIM ONE OF AMERICA’S MOST BELOVED PORTRAIT PAINTERS
By Sarahjane Blum | July 21, 2026
“To those attracted to painting portraits, I would say you must be interested in, and respond to, people. Your attitude must be a positive one. … A portrait is a personal work and must reflect the artist’s interpretation and artistry in presenting the subject.” —Everett Raymond Kinstler
When Everett Raymond Kinstler, the groundbreaking comic artist and pulp illustrator who would later eclipse his own successes to become one of the preeminent presidential and society portrait painters of the 20th century, was just 17, he paid an unannounced visit to his hero, illustrator James Montgomery Flagg. Approaching the doorman of Flagg’s posh building, the young artist was informed that Flagg was “as ornery as they come” and unlikely to grant a portfolio review to a teenage stranger. However, according to his own account, Kinstler sweet-talked his way upstairs and shared his work with Flagg, who recognized the young man’s talent and declared, “Young feller, you’re doomed to be an artist!”
During his long and illustrious career, Everett Raymond Kinstler painted the portraits of several U.S. presidents, including Ronald Reagan. This inscribed oil study for Reagan’s official White House portrait realized $45,000 in a June 2026 Heritage auction.
The anecdote is telling of much of what made Kinstler a legend: talent, boldness, and charm. August 5, 2026, marks Kinstler’s 100th birthday, and to celebrate the artist’s centennial, Heritage Auctions is offering selections from his estate across a number of auctions on and around the day itself. Last month, Heritage offered a selection of Kinstler’s presidential portraits as part of its Liberty & Legacy: 250 Years of the American Spirit auction, which notably included his study for the official White House portrait of Ronald Reagan that currently hangs in the Oval Office. The celebrations continue August 5 in Heritage’s Classic American Illustration Art Showcase Auction, which includes a selection of 40 works by the artist featuring additional pieces from his work with Gerald Ford and Bill Clinton while tracing his trajectory back to his earliest professional efforts. Additional examples from his time in the pulps can be found in Heritage’s August 11 Pulp, Paperback, Sci-Fi & Fantasy Showcase Auction.
These two studies likely were created as preparatory steps ahead of Kinstler’s 1977 portrait of President Gerald R. Ford. The pair is available in Heritage’s August 5 Classic American Illustration Art Showcase Auction celebrating the 100th anniversary of the artist’s birth.
Kinstler began working as an artist in 1942 when he was just 15, first hired as an inker at Cinema Comics before quickly lobbying to be given opportunities as a penciler, which offered greater creative freedom. He even created his own sample page in the style of Real Life Comics — “Ships and Men” — one of the earliest Kinstler works Heritage is offering. His freelance career in comics and pulps quickly took off, and throughout the 1940s and 1950s he carved out a name for himself, particularly for his westerns and romance work. Even in those early years, he earnestly pursued the study of traditional illustration and fine art techniques at the storied Art Students League under Frank DuMond and others.
By 1947, he had joined the National Arts Club alongside artists like Dean Cornwell, taking up a live-in studio in the club’s then-somewhat shabby Gramercy Park mansion a few years later. The National Arts Club would become central to Kinstler’s life. It’s where he developed a sophisticated social circle with the legendary illustrators he had long admired and, in turn, became an inspiration to generations that followed.
Kinstler created this 1943 work as a title page for a hypothetical comic book. It’s one of 40 Kinstler creations available in Heritage’s August 5 Classic American Illustration Art Showcase Auction.
Kinstler would keep his studio at the National Arts Club until his death in 2019, and it was there that he began his career as a portrait artist in the 1960s. Over the course of his career, Kinstler painted more than 2,500 commissioned portraits.
More than 100 of his works are in the Smithsonian’s National Portrait Gallery; countless others hang in private homes and institutions around the country. Often compared to John Singer Sargent for his emotional powers of perception, he became the go-to portraitist for a wide-ranging group of cultural figures, from actors like Katharine Hepburn to writers like Tom Wolfe. Wolfe posed for Kinstler in 1987, the year his seminal The Bonfire of the Vanities was published, resulting in what has become one of the defining depictions of his public persona, complete with his signature white suit, cane, and knowing expression. (A sketch for this work is included in the August 5 sale.) The portrait would grace the second edition of Kinstler’s seminal instruction manual Painting Portraits, and Wolfe would later describe sitting for his friend by saying, “If Ray couldn’t talk, he wouldn’t be able to paint.”
Among the many Kinstler highlights in Heritage’s August 5 Classic American Illustration Art Showcase Auction is this preliminary sketch for his 1987 portrait of writer Tom Wolfe.
It was this dynamic enthusiasm that gave Kinstler both insight into his subjects and made him a compelling art instructor. In addition to Painting Portraits and his other instructional books, in 2023, Kinstler’s protégé, portraitist Michael Shane Neal, published The Art of Seeing, a full-length volume compiled from notes taken during his years studying with Kinstler.
There is no overstating the mark Kinstler left on the worlds of comics, illustration, and portraiture. Known to begin his portrait sessions with the invitation, “Tell me about yourself,” Kinstler left an indelible mark on generations of artists and collectors, and Heritage’s centennial celebration offers a fitting opportunity to introduce new audiences to his beautiful and remarkably diverse body of work.
