Since its earliest performances, critics have been divided over Dream on Monkey Mountain. While most found much to praise, especially its poetic nature, some believed it to be bogged down by that very poetry. The complex play also compelled critics to offer their own widely divergent interpretations. Critics of the original New York production in 1971 exemplify this diversity.

Edith Oliver of The New Yorker saw the play as pure, successful poetry. She wrote, ‘‘Dream on Monkey Mountain is a poem in dramatic form or a drama in poetry, and poetry is rare in the modern theatre. Every line of it plays; there are no verbal decorations. A word, too, must be said for the absolute trust that Mr. Walcott engenders in his audience, convincing us there is a sound psychological basis for every action and emotion.’’

The New York Times’ Clive Barnes shared Oliver's high opinion. Barnes claimed that this ‘‘beautiful bewildering play by a poet’’ is a ‘‘richly flavored phantasmagoria.’’ Even when interpreting Walcott's intentions, Barnes came back to the poetic aspects of Dream on Monkey Mountain. He wrote, ‘‘I think that what Mr. Walcott is counseling is a twentieth-century black identity rather than an attempt to impose a reversal to a preslave black identity. But much of the play's interest is in its spectacle and poetry.’’

Another New York Times critic, Clayton Riley, generally concurred with Barnes, though he believed the play to be too wordy. Riley argued, ‘‘The play is rich and complex; the author's use of fable interwoven with a stark elaboration of historical evidence of oppression illuminates his work, lends it an arresting weight and texture. Walcott's characters are drawn with bold, sometimes extravagant strokes and, prodded by the author, they have an inclination to talk a bit too much.’’ Riley's interpretation also differed from Barnes’. Riley believed that ‘‘the thesis, as proposed in Dream on Monkey Mountain, is that the West cannot—nor should it—exist forever, given its deplorable record of racist exploitation and butchery throughout the world.’’

Barnes and Riley's colleague at the New York Times, Walter Kerr, thought the poetic tendencies of the play were problematic. He wrote, ‘‘It would be easy to misread [the play], in spite of Michael A. Schultz's admirably composed production … because the author has a strong bent towards poetic digression. He is long over some scenes that the thread of essential meaning is lost altogether; forward movement is clogged by a waterfall of words.’’

After the initial productions, Dream on Monkey Mountain continued to be presented throughout the world, including regional productions in the United States. Critics’ issues with the play remained the same. In 1979, Joseph McLellan of the Washington Post reviewed a local production. He found it ‘‘a kind of play often written by poets.… It is too long, loosely organized and specialized in interest for commercial success in this country, but striking in its use of language, fresh and original in its ideas and symbolism.’’ McLellan's interpretation focused on the dream aspect of the title. He wrote, ‘‘In a colonial society, one way to compensate for lack of power is to dream. But dreams are also a source of power and a shaping force in its use, if enough people share the dream. This is the central statement of Dream on Monkey Mountain.’’

Fifteen years later, Dream on Monkey Mountain continued to be produced regionally in the United States. Of a Boston production at Playwright's Theatre, Kevin Kelly of the Boston Globe wrote, ‘‘Deliberately paradoxical, complex to the point of confusion, Dream on Monkey Mountain is so intellectually commanding—and emotionally loaded—that you're constantly being challenged.’’ In the same review, Kelly compared the play to the Bible and Walcott to Shakespeare. Like most critics, he saw Walcott's poetic touch. He wrote, ‘‘Derek Walcott's Dream on Monkey Mountain is a great piece of work, a mesmerizing, multilayered riff that plays like a black version of the Bible with hardly any specific reference to Christian literature, but, rather, in its myth-making reach, allusive reference to all literature. It's a dense, demanding play, clearly the work of a poet posing inside the proscenium (the same posture applies to Shakespeare).’’