Lester was also a civil rights activist, a photographer,[2] and a musician who recorded two albums of folk music and original songs.

[5] In 1960 he received his BA from Fisk University in Nashville, Tennessee, with a major in English and minors in Art and Spanish.

Lester also traveled to North Vietnam with SNCC to photograph and write about the damage caused by U.S. bombing missions there.

He taught guitar and banjo and worked as a folk singer "singing at rallies, and hootenannies and fundraising events in New York for SNCC.

Lester's 1966 essay "The Angry Children of Malcolm X," is considered one of the definitive African-American statements of its era.

[14][15] He has said that his conversion journey began when he was seven and learned that his maternal great-grandfather, Adolph Altschul, was a Jewish immigrant from Germany, who married a freed slave.

[6] From 1968 to 1970, alongside his activities as a radio host in New York, Lester taught Afro-American history at the New School for Social Research.

[19] In 1988, Lester came into conflict with his colleagues in the Afro-American Studies department upon the publication of his book Lovesong, which chronicles his conversion to Judaism.

[14][20][21] In March 1988, in a unanimous step, the Afro-American Studies faculty wrote a letter to the university administration recommending that Lester be reassigned to a different department.

Du Bois"), ("Writings of James Baldwin"), ("Literature of the Harlem Renaissance"), ("Blacks and Jews: A Comparative Study"), and Judaic Studies ("Biblical Tales and Legends") and ("The Writings of Elie Wiesel"), History ("Social Change and the 1960s"), one of the university's largest and most popular courses.