He attended the Bronx High School of Science[3] and then Columbia College of Columbia University, where he studied under Mark Van Doren and Lionel Trilling and overlapped with Allen Ginsberg (Hollander's poetic mentor),[4] Jason Epstein, Richard Howard, Robert Gottlieb, Roone Arledge, Max Frankel, Louis Simpson and Steven Marcus.

[5] After graduating, he supported himself for a while by writing liner notes for classical music albums before returning to obtain an MA in literature and then a PhD from Indiana University.

[10] To Hollander, verse was a kind of music in words, and he spoke eloquently about their connection with the human voice.

[13] Hollander also composed poems as "graphematic" emblems (Type of Shapes, 1969) and epistolary poems (exampled in Reflections on Espionage, 1976),[14] and, as a critic (in Vision and Resonance: Two Senses of Poetic Form, 1975), offered telling insights into the relationship between words and music and sound in poetry, and in metrical experimentation,[15] and 'the lack of a theory of graphic prosody'.

Hollander also served in the following positions, among others: member of the board, Wesleyan University Press (1959–62); editorial assistant for poetry, Partisan Review (1959–65); and contributing editor of Harper's Magazine (1969–71).