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Frank Sinatra: Chairman of the Canvas

Singer, actor, director, philanthropist — Frank Sinatra did it all, his way. With a career spanning 60 years, the crooner is known worldwide for his swoon-worthy renditions of jazz standards, his roles in classic Hollywood films like Guys and Dolls, and his magnetic personality, but did you know he was also a gifted painter? It was one of his favorite hobbies, and his work was often inspired by mid-20th century abstract artists like Jackson Pollock and Frank Stella. Painting held an important personal significance for the singer, and he produced works for over 50 years with as much vigor and confidence as he displayed in his iconic performances.


31-1173 Untitled by Frank Sinatra


31-1173 Untitled by Frank Sinatra

Sinatra the Collector

Sinatra was a life-long lover of art and an avid art collector. He had a keen eye for collecting and owned works by major names from art history such as Pablo Picasso, Joan Miró, Childe Hassam, Marc Chagall and David Hockney. Interestingly, he even owned works by fellow crooner and sometimes artist, Tony Bennett. Undoubtedly his collecting influenced his artistic style. He surrounded himself with objects that he loved and wanted to emulate their creators.


Sinatra the Painter

Frank Sinatra took up his painting hobby in the 1940s as he was rising to fame. By the 1960s he was a huge star and a household name, but he decided to retire for a time in the 70s and 80s. It is during this time that Sinatra painted his most successful works. He did paint some representational works including landscapes, pets and a series of self portraits as a clown, but his works varied dramatically in style and subject matter. He is best known for his abstract compositions inspired by Abstract Expressionism and Minimalism.


He completed most of his later abstract paintings at his home in Palm Springs where he and his fourth wife, Barbara, spent most of their time. He had his own art studio in that estate where he often spent hours at a time, but he also enjoyed painting and sketching outside by his piano-shaped pool. Barbara observed the artist at work and said of his process, “He was, of course, Charlie Neat when it came to painting; there was rarely any mess. He only ever had one ‘Jackson Pollock moment’ that I knew of. I walked into his studio one day and found him reaching into pots of paint with his fingers and hurling it at the canvas. I don’t think he even knew I was there. Watching him lost in a world of his own creativity, I knew that art was another kind of therapy for him."



31-0248 Desert Sunset by Frank Sinatra


Desert Sunset by Frank Sinatra

Sinatra loved using geometric shapes, dynamic lines and bright colors in his compositions. He had a clear point of view as an artist, and while you can make direct comparisons to other artists’ work, he was all about interpretation. He built a hugely successful career off of singing classic jazz standards, but always made sure to make them his own. In some ways, painting was like performing for Sinatra.


Sinatra’s artistic output was celebrated in a book titled A Man and His Art: Frank Sinatra in which his daughter, Nancy Sinatra, wrote the foreword. In it, she said that her father “was the first to admit that he mimics what he’s seen, but, just as with music, it becomes Frank Sinatra’s because he stylizes it.”


Sinatra stopped painting a few years before his death in 1995 in part due to vision problems but also apparently as a result of grief. His longtime friend and fellow entertainer Jilly Rizzo tragically died in a car accident in 1992 on his 75th birthday. Tony Oppedisano, a mutual friend of Sinatra and Rizzo who had broken the terrible news of Jilly’s death to the singer, said that he never saw Sinatra pick up a paintbrush again after that.


31-0957 Untitled Abstraction by Frank Sinatra


Untitled Abstraction by Frank Sinatra

Sinatra on the Art Market

The infatuation with Frank Sinatra’s music and persona hasn’t waned one bit since his death in 1998, and interest in Sinatra as an artist has grown exponentially in recent years. In December of 2018, Sotheby’s auctioned off the estate of Barbara Sinatra which consisted of jewelry, furniture, memorabilia and artwork — including original works by Ol’ Blue Eyes himself. Sales of Sinatra paintings have exceeded pre-auction estimates with works selling in the hundreds of thousands of dollars.


As an entertainer who redefined his career many times over the 20th century, Frank Sinatra is gaining notoriety as a painter in the 21st century and redefining his image all over again. To purchase your own Sinatra painting, visit M.S. Rau or click here.


Sinatra, Frank. A Man and His Art. New York: Random House, 1991.



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