Poitier returned to Broadway, starring in Lorraine Hansberry's groundbreaking "A Raisin in the Sun" (1959). The first Broadway play written by a black woman, it was also the first directed by a black man (Lloyd Richards), and the dignified, sedate, intelligent Poitier would reprise his role in the film version two years later, beginning a string of commanding performances at the very core of his body of work. In addition to his Academy Award-winning turn in "Lilies of the Field", he starred in "A Patch of Blue" (1965), "In the Heat of the Night" and "Guess Who's Coming to Dinner" (both 1967), all turning upon the issue of race (and all winning Oscars for fellow actors Shelley Winters, Rod Steiger and Katharine Hepburn) as well as some which didn't--"A Slender Thread" and "The Bedford Incident" (both 1965). Poitier's international popularity and the mainstream middle-class roles he played during this period (authority figures such as doctors, law officers, teachers) helped pave the way for the commercial black cinema of the early 70s and were instrumental in allowing blacks to appear in less stereotypical screen roles.

Poitier debuted first as a director on Broadway, helming "Carry Me Back to Morningside Heights" (1968), and launched his second career in features with "Buck and the Preacher" (1972). He would direct five films, including "A Warm December" (1973) and the immensely popular "Uptown Saturday Night" (1974), before finally directing a film in which he did not also act, the profitable Richard Pryor-Gene Wilder pairing in "Stir Crazy" (1980). After a decade away from acting, Poitier made a much-publicized return to the screen in 1988, working opposite Tom Berenger in Roger Spottiswoode's thriller "Shoot to Kill" and playing an FBI agent in "Little Nikita". The 90s saw him assume a higher profile as a performer while putting directing on the back burner. In addition to his feature roles in movies like the high-tech caper yarn "Sneakers" (1992) and Michael Caton-Jones' political thriller "The Jackal" (1997), Poitier turned in celebrated portrayals for the small screen in the miniseries "Separate But Equal" (ABC, 1991), as Thurgood Marshall, "Children of the Dust" (CBS, 1995), "Mandela and De Klerk" (Showtime, 1997) and the CBS movie "To Sir, With Love II" (1996), in which he reprised his role from the 1967 feature.