Smiley became the first female rapper from Detroit to have a national presence in 1989 with her single “But I’m Not Friendly.” The video showed Smiley and her crew in doorknocker earrings rapping around Detroit before the days of The Rhythm Kitchen and the Hip-Hop Shop. The song earned Smiley a gold record and the video was seen on BET’s Rap City and Yo! MTV Raps. The video was so popular on the video jukebox show The Box, that many fans mailed her their phone bill after getting into trouble with their parents for requesting the video numerous times. Smiley recorded three albums for Bryant Records before leaving the rap scene to work as a model for Chrysler and a commentator for Ebony Fashion Fair. She launched and ran The Smiley Show on cable for 7 years before entering the radio industry where she worked as a program director for Radio One stations in the 2000s.