He settled in Nashville, Tennessee, where he built a law practice and taught at Fisk University. He is noted for being part of the defense team for 25 black men charged in attempted murder for the Columbia race riot of 1946 and winning acquittals for most, in the aftermath of the first major racial confrontation in the United States after World War II. He participated in numerous other cases, including leading desegregation of schools in Nashville. He served as a Republican member of the Nashville City Council from 1951 to 1971. His house was bombed by segregationists on April 19, 1960.
Looby was born on April 8, 1899 in Antigua. His father was John Alexander and his mother, Grace Elizabeth Joseph. When he was five, his mother died while giving birth to a sibling. His father died when Looby was a teenager. The youth moved to the United States in 1914 as an orphan when he was fifteen years old.