Gil Caldwell was born in Toronto and began his career as a commercial artist at Saturday Night Press. He attended the Ontario College of Art, and after graduation enrolled in the Toronto Teachers College. He accepted a position as an art teacher in Etobicoke, where he remained for his 32-year teaching career. While teaching, he continued his own education and received a Bachelor of Arts from McMaster, a Bachelor of Education from the University of Toronto and a Master of Education from Niagara University, U.S.A. in 1980. He is recognized as a master watercolourist and printmaker, who has long been regarded as one of the best in his field.
A move from classroom teaching to an administrative position as vice-principal greatly impacted the development of his artistic style. Formerly he painted to relax and unwind, but as he was no longer teaching art he had the desire to further explore his own artwork. He worked long hours developing and perfecting his style. Since his retirement in 1988, he has taken the opportunity to pursue art as a full-time calling. He calls his works composites of ideas gathered from on-site sketches and photographs that suggest a naïve quality. He uses bright colours, detail and strong design elements. He is renowned for his pictures of houses, and favours urban and rural scenes.
Caldwell was named Mississauga's Visual Artist of the Year in 2001. His work has appeared on Reader's Digest covers and in Ontario Living and Canadian Art Magazine . He was the first Canadian artist featured in North Light , an American art book magazine. His works have been exhibited in Canada and around the world including the Art Gallery of Mississauga and the Region of Peel Art Gallery, and have been shown in solo, group, rental and juried exhibitions at the Mississauga Living Arts Centre, Art Gallery of Toronto and the Wallace Gallery in Calgary, among many others. In 2005, Gil was appointed as President of the Colour and Form Society. Caldwell encourages younger emerging artists on a consistent basis. He recently lectured art students at Bronte College, with emphasis not only on his own work, but also, on the trials and tribulations of being a full-time artist. He has donated his works for many fundraising events, including those for the Children's Aid Society, Credit Valley Hospital, Alzheimer's Society, Cancer Society and Muscular Dystrophy Association.
He was recognized for his community service with a Volunteer Award for Outstanding Contribution of Service in 2004. Caldwell and his wife, Betty, have three daughters and currently reside in Mississauga.