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From 1977-80 he attended the Ontario College of Art, followed by 17 years working in the Art & Photography Department of the Hospital For Sick Children in Toronto, in their art therapy program. Inspired by surrealists such as Frida Kahlo and Salvador Dalí, Caesar's experiences at the Children Hospital deeply influenced his artwork. Caesar said: "Working in a photography department in a Children's hospital is the act of chronicling everything from child abuse, re-constructive surgery, to the heroic children that deal with the hardship and challenges that life has to offer. I spent many years creating medical and research documentation, medical and technical drawings, images of huge equipment surrounding tiny premature infants and visual tools for brain-damaged children".
From 1998 to 2001 he worked as a senior animator in GVFX, Toronto, where he mastered his skills in using 3D modelling software.
Ray Caesar's portraits frequently involve childlike creatures with physical deformities and grotesque elements set against a fairy tale backdrop of darkness and sexual innuendos. In his creations he merges elements of decorative styles and architectural ages, mixing Art Decò, Victorian style and visual codes from the early 1900s.
Caesar describes his process as "I begin by automatic drawing which is basically just letting your hand do first what your mind hasn't thought about. This evolves and I begin modelling in a 3D software called Maya pretty much the same way. I set the digital figure up for animation and I can move each finger and have a wide range of facial expressions, I do dynamic simulations of cloth and begin using curves to style hair. Lights and textures and 3D environments and referencing older models I built years ago come into the virtual space. I love that I can hide old letters and photographs in lockets and tuck them away into drawers that are closed. I know they are there and that seems important to me and I love that sometimes I forget they are there. In many ways working in a virtual environment is like being in a dissociative fugue or very deep daydream or in your very own playroom...you can get lost in there very easily. Somehow the piece just evolves into what it wants to be".
In 1999, Caesar received a Primetime Emmy Nomination for Outstanding Special Visual Effects for his work on Total Recall 2070, a Gemini Nomination for Special Effects  and a Monitor Award for Special Effects in a series. 
Ray Caesar is inspired by French Genre artists such as Fragonard, Chardin, Francois Boucher, Jean-Baptiste Perronneau, as well as American realists such as George Tooker, Paul Cadmus and Edward Hopper and surrealists like Salvador Dalí and Joseph Cornell. He also mentioned he's inspired by Mary Cassat and Frida Kahlo.
Ray Caesar is represented by Gallery House in Toronto, Canada. His works have been shown in several international exhibitions.
His most significant solo shows are listed below:
- 2015 - "Pretty Little Predators", Gallery House, Toronto, Canada 
- 2014 - "The Trouble With Angels", Palazzo Saluzzo Paesana, Turin, Italy 
- 2014 - "The Trouble With Angels", Dorothy Circus Gallery , Rome, Italy 
- 2013 - "Ray Caesar", Corey Helford Gallery Retrospective Show, Culver City, LA, USA
- 2012 - "Ray Caesar", Kochxbos Gallery, Amsterdam The Netherlands
- 2011 - "A Gentle Kind Of Cruelty", Jonathan LeVine Gallery, New York, USA 
- 2011 - "Solo show", Corey Helford Gallery, LA California, USA
- 2010 - "I Sogni Di Cristallo", Mondo Bizzaro Gallery, Rome, Italy 
- 2007 - "Ipso Facto", Richard Goodall Gallery, Manchester, England 
- 2006 - "Sweet Victory", Jonathan LeVine Gallery, New York, USA 
- 2005 - "Secret Doors and Hidden Rooms", Jonathan LeVine Gallery, New York, USA 
- Ray Caesar, Art Collection, Volume 1. Mark Murphy Designs, 2008.
- Ray Caesar, Ipso Facto. Richard Goodall Gallery Exclusive, 2007.
Caesar, who was born in England and moved with his family to Canada in 1967, says that issues with his father contributed to the arrival of Harry, an "alternate," when he was 10. The boy is disguised as a girl in Caesar’s art, and remains present in his daily life as an alter ego. "Harry is beyond anger – he enjoys it," says Caesar. "My job is to keep Harry under control."
Caesar has discussed openly he suffers from Dissociative Identity Disorder and that witnessing things like child abuse, surgical reconstruction, mental illness, and animal research all had a deep effect on him.
Caesar is married to his wife Jane and lives in Toronto, Canada.
- "PRESSKIT1". raycaesar.com. Retrieved 21 November 2015.
- "Ray Caesar, the Canadian artist who turned down Madonna". The Globe and Mail.
- "In The Mind of Ray Caesar". Empty Lighthouse Music & Arts Magazine.
- "Ray Caesar". Television Academy.
- "Dorothy Circus Gallery". Dorothy Circus Gallery. Retrieved 21 November 2015.
- "Ray Caesar in A Magazine". jonathanlevinegallery.com. Retrieved 21 November 2015.
- "Exhibitions ‹ GALLERY HOUSE – Ray Caesar, Andre Fauteux, Gottfried Helnwein, Brian Richer, Carol Sutton, Selena Wong & Myron Zabol – Art Gallery Toronto". galleryhouse.ca. Retrieved 21 November 2015.