Damon is a Harlem, New York City, native. His father, Howell Stouten Wayans, was a grocery store manager, and his mother, Elvira Alethia, was a homemaker who sang and also worked as a social worker.
He has four brothers and five sisters growing up. As a child, Damon suffered from clubfoot. It is a deformity of the foot in which the affected foot is rotated at the ankle.
In New York, he attended Murry Bergtraum High Institution, a public school. Despite coming from a low-income family, he has no negative memories. Damon quit school in the ninth grade and began working odd jobs to support himself.
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