Smallwood was employed as a postal worker and began rapping in the mid-1980s. She took first place in a rap contest at a South-Central Los Angeles roller rink with an anti-drug themed rap.[2] By 1988 she had formed a group with her son called Rappin' Granny and DJ Len.[3] She won a Granny of the Year contest in Pasadena in 1988, performing a rap version of the song "The Little Old Lady from Pasadena".[2][3] In 1989, she released a little-known, self-titled music video called "Rock-n-Soul".[4] Smallwood was signed to Tandem Records in 1992. She released the single "You Didn't Use Your Blinker Fool" as a response to the DJ Jazzy Jeff & The Fresh Prince song "You Saw My Blinker".[2] A brand of soda, Rappin Granny's Slammin Strawberry Hip Hop Pop, was named for her in 1995.[5]
Smallwood was featured in the Apollo Theater's Apollo Circus of Soul in 2007.[8]
America's Got Talent
Smallwood was a contestant on the NBC television series America's Got Talent[9][10] and qualified on the August 16, 2006 season finale for the one-million-dollar grand prize. In her audition, Rappin' Granny gave a performance that was very popular among the crowd and the judges, all of whom (Brandy, David Hasselhoff, and Piers Morgan) advanced her to the next round by way of a unanimous vote. Smallwood then returned for the semifinal episode that aired July 26, 2006. After another crowd-pleasing song, the judges again put her through to the next round, by another unanimous vote. For the final round, Smallwood rode in on a motorcycle, but finished in the bottom half of the public vote.[11]