In 1999, the soundtrack to the movie Wild Wild West featured his song "The Stick Up" with his mentor Jermaine Dupri. Unlike his previous albums, this one was not produced under the mentorship of Jermaine Dupri.
At the age of 13, in 2000, he debuted with Beware of Dog under the stage name Lil' Bow Wow. Bow Wow appeared on the remix of Jo Jo's single "Baby It's You" in 2004. Its first single was "Let Me Hold You", featuring Omarion, and peaked at #1 on the rap chart and #4 on the Hot 100.
The music video for the song was directed by Bow Wow's personal cameraman Rico Da Crook and was a success on 106 & Park and made it to the top of the countdown.
The third single scheduled from the album was intended to feature Miguel that was titled "Right Now".
On August 16, Bow Wow announced his signing to Cash Money Records, joining an all-star roster that already includes Nicki Minaj, Drake, Lil Wayne and Birdman, among others.