By the age of seven, Ali had begun her singing career. She also appeared with Herbie Hancock on an episode of Sesame Street. By age five, she won Star Search two times. She made her breakthrough when she was cast as Ashley Banks for the popular television sitcom Fresh Prince of Bel-Air. She sang on various episodes of the show. On one of the shows Ali sings Aretha Franklin's "Respect" and the original song "Make Up Your Mind" produced by Rob Jay of Nspyre Music Productions. Will Smith asked her if she seriously considered pursuing a musical career. Despite her singing ability, she concentrated on her acting career on Fresh Prince the next few years. Ali was said to be closest to her co-star Janet Hubert-Whitten.

In the penultimate season of Fresh Prince, Ali began preparing herself for her musical debut. The result was the album Kiss The Sky, which was certified gold in early 1999. The album spawned the hit song "Daydreamin'", produced by Rodney "Darkchild" Jerkins, which peak