A Ford Foundation program allowed Lipsyte to skip his senior year at Forest Hills High School in Queens and enroll at Columbia University, from which he earned a Bachelor of Arts degree in 1957 at the age of nineteen. In 1959, Lipsyte received a Master’s degree from the Columbia University School of Journalism.
Although he planned to move to California after graduating from Columbia as a nineteen-year-old English major, Lipsyte took a summer job as a copy boy in the sports department of the New York Times. Eventually becoming a sports reporter and then a sports columnist, he stayed with the newspaper for fourteen years. During that time, he co-authored Nigger (1964) with controversial comic and activist Dick Gregory; published The Masculine Mystique (1966); wrote his first and best-known novel, The Contender (1967); and published an edited collection of his columns, Assignment: Sports (1970).
After 1971, Lipsyte worked as a freelance writer, television scriptwriter, journalism professor, radio commentator (National Public Radio, 1976–82), and columnist for the New York Post (1977). He was a television sports essayist for CBS Sunday Morning (1982) and stayed with that network until moving to NBC in 1986. After leaving NBC in 1988, he hosted The Eleventh Hour on PBS (1989), winning an Emmy Award for On-Camera Achievement although the show was canceled after its second season. Returning to the New York Times to write a sports column in 1991, Lipsyte continued freelance writing while beginning a column in 1992 in the magazine American Health.
Lipsyte married Maria Glaser in 1959; they divorced in 1963. In 1966, he married novelist Marjorie Rubin; they had a son, Sam (1968) and a daughter, Susannah (1971). His second marriage ended in 1987. He married television producer Katherine L. Sulkes in 1992.
