linguistic:paraphrasing, structural:reformatting
1958–1969: Breakthrough and stardom

In 1958 he starred alongside Tony Curtis in director Stanley Kramer 's The Defiant Ones. The film was a critical and commercial success with the performances of both Poitier and Curtis being praised. The film landed eight Academy Award nominations including Best Picture and Best Actor nominations for both stars, making Poitier the first Black male actor to be nominated for a competitive Academy Award as best actor. Poitier did win the British Academy Film Award for Best Foreign Actor.

Poitier acted in the first production of A Raisin in the Sun alongside Ruby Dee on the Broadway stage at the Ethel Barrymore Theatre in 1959. The play was directed by Lloyd Richards. The play introduced details of Black life to the overwhelmingly White Broadway audiences, while director Richards observed that it was the first play to which large numbers of Black people were drawn. The play was a groundbreaking piece of American theater with Frank Rich, critic from The New York Times writing in 1983, that A Raisin in the Sun "changed American theater forever". For his performance he earned a Tony Award for Best Actor in a Play nomination. That same year Poitier would star in the film adaptation of Porgy and Bess (1959) alongside Dorothy Dandridge. For his performance, Poitier received a 1960 Golden Globe Award nomination for Best Actor in a Motion Picture Musical or Comedy.

If the fabric of the society were different, I would scream to high heaven to play villains and to deal with different images of Negro life that would be more dimensional... But I'll be damned if I do that at this stage of the game. Not when there is only one Negro actor working in films with any degree of consistency...

Sidney Poitier (1967)

In 1961, Poitier starred in the film adaptation of A Raisin in the Sun for which he received another Golden Globe Award nomination. Also in 1961, Poitier starred in Paris Blues alongside Paul Newman, Joanne Woodward, Louis Armstrong, and Diahann Carroll. The film dealt with the American racism of the time by contrasting it with Paris's open acceptance of Black people. In 1963 he starred in Lilies of the Field. For this role, he won the Academy Award for Best Actor and became the first Black male to win the award. His satisfaction at this honor was undermined by his concerns that this award was more of the industry congratulating itself for having him as a token and it would inhibit him from asking for more substantive considerations afterward. Poitier worked relatively little over the following year; he remained the only major actor of African descent and the roles offered were predominantly typecast as a soft-spoken appeaser.

In 1964, Poitier recorded an album with the composer Fred Katz called Poitier Meets Plato, in which Poitier recites passages from Plato 's writings. He also performed in the Cold War drama The Bedford Incident (1965) alongside the film's producer Richard Widmark, the Biblical epic film The Greatest Story Ever Told (1965) alongside Charlton Heston and Max von Sydow, and A Patch of Blue (1965) co-starring Elizabeth Hartman and Shelley Winters.

In 1967, he was the most successful draw at the box office, the commercial peak of his career, with three popular films, To Sir, with Love, and In the Heat of the Night, and Guess Who's Coming to Dinner. Although these three films seemingly shared little similarity, they all, albeit not overtly, dealt with the black and white divide. In To Sir, with Love, Poitier plays a teacher at a secondary school in the East End of London. The film deals with social and racial issues in the inner city school. The film was met with mixed response; however, Poitier was praised for his performance, with the critic from Time writing, "Even the weak moments are saved by Poitier, who invests his role with a subtle warmth."

In Norman Jewison 's mystery drama In the Heat of the Night, Poitier played Virgil Tibbs, a police detective from Philadelphia who investigates a murder in the Deep South in Mississippi alongside a cop with racial prejudices played by Rod Steiger. The film was a critical success with Bosley Crowther of The New York Times calling it "the most powerful film I have seen in a long time." Roger Ebert placed it at number ten on his top ten list of 1967 films. Art Murphy of Variety felt that the excellent Poitier and outstanding Steiger performances overcame noteworthy flaws, including an uneven script. Poitier received a Golden Globe Award and British Academy Film Award nomination for his performance.

In Stanley Kramer's social drama Guess Who's Coming to Dinner, Poitier played a man in a relationship with a White woman played by Katharine Houghton. The film revolves around her bringing him to meet with her parents played by Katharine Hepburn and Spencer Tracy. The film was one of the rare films at the time to depict an interracial romance in a positive light, as interracial marriage historically had been illegal in most states of the United States. It was still illegal in 17 states—mostly Southern states—until June 12, 1967, six months before the film was released. The film was a critical and financial success. In his film review, Roger Ebert described Poitier's character as "a noble, rich, intelligent, handsome, ethical medical expert" and that the film "is a magnificent piece of entertainment. It will make you laugh and may even make you cry." To win his role as Dr. Prentice in the film, Poitier had to audition for Tracy and Hepburn at two separate dinner parties.

Poitier began to be criticized for being typecast as over-idealized African-American characters who were not permitted to have any sexuality or personality faults, such as his character in Guess Who's Coming to Dinner. Poitier was aware of this pattern himself but was conflicted on the matter. He wanted more varied roles; but he also felt obliged to set an example with his characters, by challenging old stereotypes, as he was the only major actor of African descent being cast in leading roles in the American film industry at the time. For instance, in 1966, he turned down an opportunity to play the lead in an NBC television production of Othello with that spirit in mind. Despite this, many of the films in which Poitier starred during the 1960s would later be cited as social thrillers by both filmmakers and critics.