Gooding, Jr.'s first major film role was in director John Singleton's 1991 film, Boyz N The Hood, a well-reviewed film about inner city youths. Prior to this, he had appeared in many TV shows, including a recurring role on MacGyver. Following the success of the film, he was cast in a series of roles, both leading and supporting, including the 1996 film, Jerry Maguire, for which he won a Best Supporting Actor Oscar.

Cuba took his first shot at producing with long time manager and partner Derek Broes. Broes and Gooding tapped long time friend Rowdy Herrington as the writer director of the film A Murder of Crows. The film has gained cult status among murder mystery buffs. Broes later left Hollywood for the technology world and now sits in an executive chair at Microsoft Corporation.

Gooding, Jr.'s subsequent career has included box office successes like Men of Honor (in 2000), Snow Dogs (in 2002), and a supporting role as Navy Cross awardee Doris Miller in the 2001 film, Pearl Harbor.

In 2006, he appeared in the crime-drama, Dirty, which received a limited theatrical release, as well as the direct-to-dvd, 24-esque politcal drama End Game where he plays a Secret Service agent who uncovers a conspiracy after a Presidential assassination.

He also hosted the 37th Annual NAACP Image Awards.

After a string of comedies that were mostly disliked by critics, Gooding, Jr. has vowed to never appear in another comedy again, saying that he "thought people wanted me to make them laugh, but I was wrong on so many levels. I try to take all my energy and take it into comedy, and that's when I'm terrible".

Gooding, Jr. is married to schoolteacher Sara Kapfer, whom he has known since 1986; they have three children, Spencer, Mason, and Piper.

He is a fan of hockey and in January 2006, Cuba made an appearance as a guest announcer for the Los Angeles Kings in one game. He also has a very minor part in Coming to America as the customer in the barbershop scene.