He may play legendary jazz musician Miles Davis in an upcoming biopic. Cheadle earned his first nomination by portraying real-life hotel manager Paul Rusesabagina in Hotel Rwanda.
Playing a real person seems to be the best way to obtain an Academy Awards nomination. Philip Seymour Hoffman won for playing Truman Capote, and Reese Witherspoon won for playing June Carter Cash. Of the twenty total acting nominations, nine were for portraying a real person. Last year, Jamie Foxx won for portraying Ray Charles, and Cate Blanchett was honored for her performance as Katherine Hepburn.
This article from USA Today is specifically about the 77th Academy Awards - held last year - yet is still relevant.