Gooding's first job as a professional entertainer was as a breakdancer performing with singer Lionel Richie at the closing ceremoines of the 1984 Summer Olympics in Los Angeles. Following high school, Gooding studied Japanese martial arts for three years before turning his focus toward acting. Early on, he landed guest starring roles on shows like Hill Street Blues (1981) and MacGyver (1985). His first major role was in the 1991 box office surprise Boyz n the Hood (1991). He followed this success with roles in major films like A Few Good Men (1992), Lightning Jack (1994), Outbreak (1995), The Fighting Temptations (2003), and most recently, Daddy Day Camp (2007) and Hero Wanted (2008).

In 1996, Gooding was cast as an arrogant, football player on the brink of career ending injury in Cameron Crowe's Jerry Maguire (1996). The film became a huge box office smash and earned him an Academy Award for Best Supporting Actor. His "Show Me The Money" line in the movie became a nationwide