In 1949, the artist had his first solo show at the Jane Street Gallery, an artist’s co-op in the Village. Larry Rivers received favorable reviews and was invited to join the Tibor de Nagy Gallery uptown. In 1951, he earned a BA from New York University in art education, but he chose to become an artist full time instead of a teacher as he had planned. Instead Larry Rivers developed a career that focused on painting, but included music, stage design, acting, filmmaking, writing poetry and prose.

He was a facile draftsman whose artwork formed a connection between the Abstract Expressionism of the 1940′s and 1950′s and Pop Art in the 1960′s. Larry Rivers belonged to the second generation of the New York School of painters. Unlike most of his contemporaries, the artist stayed away from abstraction instead preferring narrative paintings. A post-Abstract Expressionist, Larry Rivers was one of the first artists to rebel against the pure abstraction movement and inject recognizable figurative subjects into his painting. He established a middle ground between Abstraction and Realism and combined blurred images with precise lines.

Larry Rivers was very much a part of the leading-edge New York art scene. He continued to show annually at the Tibor de Nagy Gallery from 1952 to 1962. During his career, he was fascinated by great painting. The best known paintings of Larry Rivers were his versions of some of the most famous paintings by masters such as Édouard Manet, Rembrandt and Emanuel Gottlieb Leutze. In 1955, The New York Museum of Modern Art acquired the painting Washington Crossing the Delaware and in 1956 the Whitney Museum purchased Double Portrait of Berdie which are two of the more famous Larry Rivers paintings. In 1957, he also began making welded steel sculpture. In 1963, the artist joined the Marlborough Gallery where he stayed until his death. He had periodic museum shows in Europe and the United States throughout his career.

In 1945, the artist married Augusta Burger and they had a son Steven and Joseph was her son from a previous marriage. In 1961, Larry Rivers married Clarice Price and had two daughters Gwynne and Emma. In the 1970′s, he had another son Sam with the painter Daria Deshuk. The subjects of the figurative paintings of Larry Rivers were family, history, politics, religion and sex. His oil paintings often included the use of stencils, cutouts, blank canvas and image reversals. He often painted family members including his mother in law, his sons and his ex-wife.