Will Smith is a famed actor who has so many iconic movie roles in Hollywood blockbusters under his belt you sometimes forget he’s an accomplished rapper, too.

Smith started as the MC of the hip-hop duo “DJ Jazzy Jeff & The Fresh Prince,” with his childhood friend Jeffrey “DJ Jazzy Jeff” Townes as turntablist and producer. They gained critical acclaim and won the first Grammy awarded in the Rap category (1988).

As a result of spending money carelessly, Smith was nearly bankrupt in 1990, when the NBC television network signed him to a contract and built a sitcom, The Fresh Prince of Bel-Air, around him.

The show was successful and began his acting career. Smith has since gone on to become one of the most well-known and highest paid actors in the world.