There are many drawings from Al Hirschfeld’s 82 year career that remain iconic with the passage of time. Hirschfeld’s 1977 portrait of Richard Kiley in Man of La Mancha is such a drawing. The soft curves of feathers in Kiley’s hat hold their shape, and his exaggerated mustache seems it was groomed only yesterday. Hirschfeld retains the classic line figure that he perfected over the years and juxtaposes it with the fine detail of Kiley from his torso up.

Agnes Mongan, curator of the Fogg Museum at Harvard University went straight to her boss after seeing the drawing and pleaded that Harvard must acquire the work. “He’s never going to get any better than this.” While “better” is in the eye of the beholder, Hirschfeld still had another 25 years of drawing to do. The alumni that helped raise the money to acquire the work, Mel Seiden had a great affinity for art of all kinds, and recognized the brilliance and exquisite line of the drawing. The drawing found a home at the Fogg Museum at Harvard, starting a trend of Harvard acquiring Hirschfeld’s work into what is now the largest public collection of his work in the world. The Theatre Collection at Harvard is the largest and the first collection of its kind.

Robert Taylor reviewed a selection of Hirschfeld’s work from the Melvin Seiden collection at Harvard University in the Boston Sunday Globe in 1988, “The latest images, such Richard Kiley in Man of La Mancha or John Lithgow in M. Butterfly deploy white paper as a support for a breathtaking line that swoops, curls and spins often in a single continuous stroke. The masters of Chinese and Japanese ink brush painting practiced the same intense gestural economy, the same winnowing of the extraneous to enhance their line’s dramatic swell and fall. In Al Hirschfeld’s most recent pictures, line itself assumes center stag, an actor of authoritative powers in a classic role.”

The musical tried out in Connecticut and New York, and eventually made its way to the Martin Beck Theatre on November 22, 1965. Hirschfeld supplied the signature art for the show, with the image appearing on posters, programs and cast album. The show took home the most awards at the 20th Tony Awards, including Best Musical and Best Performance by a Leading Actor in a Musical, for Richard Kiley. The original run lasted until 1971, with 2,328 performances. The show would be revived for the first time only a year later in 1972 at the Vivian Beaumont Theatre. Kiley reprised his role until its close four months later. A third revival would also star Kiley in 1977, and would result in the drawing of the subject of this article. This portrait from 1977 would be Hirschfeld’s last drawing of Kiley, and there simply is no better portrayal of Kiley, or Don Quixote for that matter.

Kiley was first drawn in 1959 in a production of Redhead with costar Gwen Verdon in a composite of “Players Who Play Performers.” Over the next 16 years, Hirschfeld drew Kiley 10 times, four of which were as Don Quixote. In 1976, Hirschfeld began doing drawings for the Times every Friday for their theater column. These works are commonly referred to as “Friday drawings.” Kiley was in Hirschfeld’s first Friday drawing with Jane Alexander, starring in a revival of The Heiress.

Man of La Mancha returned to Broadway in 1992 at the Marquis Theatre, and once more in 2002, back to its beginnings at the Martin Beck Theatre (now known as the Al Hirschfeld Theatre). During the run of the show, on June 21, 2003, the theatre was renamed as the Al Hirschfeld Theatre.