While Singleton was attending the Film Writing Program at USC, he won three writing awards from the university, which lead to a contract with Creative Artists Agency during his sophomore year. He was also a recipient of the Jack Nicholson Award in 1989 and 1990, and the Robert Riskin Award in 1989. USC School of Cinema-Television invited him to speak at the 2006 Commencement. He received the Mary Pickford Alumni Award in May 2006.

Singleton exploded on to the scene with his first film, BOYZ N THE HOOD (1991), a tough, intelligent, plain-speaking look at friends in gang-ridden South Central L.A. that earned him an Oscar nomination for Best Original Screenplay and Best Director, becoming the first African-American (and the youngest filmmaker) ever to do so. Singleton has won numerous awards such as the LAFCA New Generation Award in 1991 and the MTV Movie Award for Best New Director in 1992 (the Award for Directorial Debut of the Year BOYZ IN THE HOOD). He has also directed a few television commercials for Coca-Cola and AT&T with D. L. Hughley.

He directed 2 Fast 2 Furious (2003) starring Paul Walker, Tyrese Gibson and Ludacris in Miami, and Four Brothers (2005) staring Mark Walhberg, Tyrese Gibson, and Andre 2000 in Canada. Both projects were summer hits. Baby Boy (2001), a film he wrote, produced and directed starring Tyrese, Ving Rhames, Snoop Dogg and newcomer Taraji P. Henson, received four NAACP nominations. Singleton wrote, produced and directed the remake of the 70’s classic Shaft (2000) starring Samuel Jackson for Paramount Pictures. Before that, he wrote, produced and directed Higher Learning (1995) starring Omar Epps and Laurence Fishburne, and wrote, produced and directed Poetic Justice (1993) staring Janet Jackson and Tupac Shakur. He also produced and funded the independent film Hustle & Flow (2005), starring Academy Award nominee Taraji P. Henson, Terrence Howard and Anthony Anderson. This film went on to receive an Academy Award for Best Song of 2005 entitled “Its Hard Out Here For a Pimp.”

Singleton broadened his scoop when he produced a Latin flavored project entitled Illegal Tender. Filming took place in Puerto Rico: it was released in late summer 2007 and distributed by Universal Pictures. He also directed the action film Abduction (2011) starring actor Taylor Lautner of the Twilight film series. Abduction was released in 2011 by Lionsgate Studios.

Singleton has recently directed an episode of Empire and an episode of the new series, American Crime Story, entitled “The OJ Simpson Trial”. He is currently working with FX on his first Television Production entitled Snowfall which is scheduled for 2016 as well.

He has privately mentored emerging filmmakers in areas such as story content (writing) and independent filmmaking. Singleton is on the Board of the Western Directors Council, Member of University of California SCA Alumni Development Council, and the Academy Film Scholars—Institutional Grants Committee. He is teaching a Film Culture class at USC which began in January 2016.