She first was brought into the public eye as a featured background vocalist on Vita's 2001 hip hop remake of Madonna's "Justify My Love," which appeared on the soundtrack to the movie "The Fast And The Furious". That same year, she caught the attention of Fat Joe, and he invited her to sing background for Big Pun's unsuccessful posthumous single "How We Roll".
Ashanti's big break, however, didn't come until early 2002, when, almost simultaneously, Ja Rule released the song "Always On Time" and Fat Joe released "What's Luv". They were two of the biggest pop hits of the year, and both featured Ashanti. Shortly afterwards, Ashanti released her own single, "Foolish," which contained a simple of the late Biggie Smalls' hit song, a remix of "One More Chance". It was the year's biggest hit, according to Billboard, spending eleven weeks at number one on the pop charts, thanks in part to a remix called "Unfoolish," which featured a rap by Biggie, and got heavy urban radio airplay. Ashanti's follow-up singles, "Happy" and "Baby" were smaller hits later that same year. During the summer of 2002, Ashanti also appeared on a Ja Rule song called "Down 4 U," along with labelmates Vita and Charli Baltimore.
In early 2003, Ja Rule and Ashanti teamed up again and scored a massive hit with "Mesmerize".
In summer of 2003, she released an album called Chapter 2. Its first single, "Rock Wit U (Awww Baby)" became one of the summer's biggest hits and its steamy video, which showed Ashanti in a bikini frolicking on a beach, was nominated for a 2003 MTV Video Music Award for Best R&B Video. The second single, "Rain On Me" was released in the fall of 2003 and has not yet been able to reach "Rock Wit U"'s level of success on either pop or urban radio.