He made his feature film debut writing and directing Boyz n the Hood (1991), for which he was nominated for the Academy Award for Best Director, becoming, at age 24, the first African American and youngest nominee in the category.

Singleton frequently cast rappers and musicians, such as Ice Cube, Tupac Shakur, Janet Jackson, Q-Tip, Busta Rhymes, Tyrese Gibson, Snoop Dogg, Ludacris and André 3000 in prominent roles.

[3] In a 1993 DIRT magazine interview with Veronica Chambers, Singleton says of his childhood, "When I was growing up, comic books, video games and movies were my buffer against all the drugs, the partying and shit [...] I never grew up with a whole lot of white people.

In 1991, Singleton made his feature film debut with Boyz n the Hood, a coming-of-age crime drama about three childhood friends growing up in the crime-ridden neighbourhood of South Central LA.

Starring Cuba Gooding Jr., Ice Cube, Nia Long, Morris Chestnut, Angela Bassett, Regina King, and Laurence Fishburne, the film was both a critical and commercial success.

[7] In 1992, following the success of Boyz n the Hood, Singleton went on to direct VFX-driven "Remember the Time" music video for Michael Jackson, which featured Eddie Murphy, Iman, and Magic Johnson.

In 1993, Singleton wrote and directed his second film, Poetic Justice, a romantic drama about a young African-American woman named Justice (played by Janet Jackson, in her film debut) who writes poetry to deal with the loss of her boyfriend to gun violence but soon encounters a postal worker (played by Tupac Shakur), who helps her overcome depression.

The film received mixed reviews from critics, but earned Jackson Academy Award and Golden Globe nominations for Best Original Song for "Again", which reached number one on the Billboard Hot 100.

"[9]In 1997, following the mixed reception of Poetic Justice and Higher Learning, Singleton's fourth film, Rosewood, a historical drama based on racial violence during the 1923 Rosewood massacre in Florida, received generally positive reviews and was entered into the 47th Berlin International Film Festival, where it was nominated for the Golden Bear.

[10] In 2000, Singelton co-wrote, co-produced and directed Shaft, a sequel-remake of the original 1971 film of the same name starring Richard Roundtree in the title role.

Also starring Anthony Anderson and Taraji P. Henson in supporting roles, the film received positive reviews and earned two Academy Awards nominations for Best Actor and Best Original Song, winning the latter.

Following the release of the critically-panned action thriller film Abduction (2011), Singleton spent the final years of his career focusing on television.

After directing episodes of the critically acclaimed TV shows Empire and American Crime Story, in 2017, he served as an executive producer and director of the crime drama series Rebel for BET, which focuses on Oakland police officer Rebecca "Rebel" Knight, who after her brother was killed by police, began working as a private investigator.

That same year, Snowfall, a crime drama series co-created and executively produced by Singleton for FX, premiered on July 5, 2017.

Singleton co-wrote the screenplays for the first two episodes with series creators Eric Amadio and Dave Andron and directed the finales for the first two seasons.

The two met in 1986, at a screening of Lee's film She's Gotta Have It, two weeks before Singleton started attending the University of Southern California (USC).

[24] On August 23, 2007, Singleton was involved in an automobile accident in which he struck a jaywalking pedestrian, Constance Russell, 57, of Los Angeles.

Singleton told an audience of students at Loyola Marymount University "They ain't letting the black people tell the stories."

[37] American rapper and actor Ice Cube, who worked with Singleton in Boyz n the Hood and Higher Learning, said: "There are no words to express how sad I am to lose my brother, friend & mentor.

"[38] A private funeral was held on May 6, 2019, in Los Angeles, and Singleton was buried at Forest Lawn Memorial Park, Hollywood Hills.