Les Benjamin was born on April 29, 1925, in Medicine Hat, Alberta. He was raised in southwestern Saskatchewan and southeastern Alberta. Benjamin enlisted in the air force during World War II, but spent much of his time in the armed forces fixing the Alaskan Highway. He worked for the CPR as a telegrapher, station agent and manager. As a CCF activist, Benjamin made two unsuccessful runs for provincial office in the riding of Maple Creek. By 1961 he had become the provincial secretary for the New Democratic Party, a position he held until 1968.
That year Benjamin ran for federal office in the riding of Regina-Lake Centre. He won, beginning a twenty-five-year political career. While in the House of Commons, Benjamin worked on the transportation committee. “Boxcar Benjamin” was an outspoken critic on the subject of grain transportation. He resigned from his seat in 1993.
Benjamin was married twice: in 1950 to Marjorie Kathleen McKinnon (Kay), and then to Constance Freisen in 1976. He had three children and two stepchildren. Les Benjamin lost his battle with cancer on June 16, 2003. The city of Regina has honoured Les Benjamin by naming a crescent in his honour.