Jack Gilbert was born in Cleveland Ohio. He received his BFA in 1978 from the California College of Arts and Crafts and his MFA in 1982 from Rutgers University where he also taught drawing and painting. After receiving his degrees Jack moved to New York. He kept a studio in Williamsburg and showed paintings in a number of solo and group exhibitions at galleries such as White Columns (1986), Cable Gallery (1987), and the Michael Walls Gallery (1989, 1990), among others. He also held solo exhibitions at the Betsy Rosenfield Gallery in Chicago in 1988 and in 1989 at the Galerie Folker Skulima in what was then West Berlin.

In the summer of 1993 Jack left New York and returned to his family home in Southern Vermont, where he raised a family and ran a successful restaurant and food business. In 2022 Jack returned to painting and is making new work for the first time in 30 years. Where Jack's earlier work in the 1980s was primarily concerned with the revitalization of painting in all of its forms, from neo expressionism to the work of the Pictures Generation, his new work pursues a sense of place, history, and meaning in landscape through the painting practice.