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In 1998, at the age of eleven, Bow Wow met record producer Jermaine Dupri, who helped shape his career. The second single was then released, "My Baby", featuring Jagged Edge.
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.
All these Lil' rappers, I'm just kind of getting real irritated by it. On July 4, 2009, his new song "I Know I'm The Shit" off his DJ Drama-hosted Mixtape, he makes a references working on his new album Underrated and that it is already in production.
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.
Bow Wow made his first movie appearance in All About the Benjamins, in 2002 as a cameo.
In the same year, Bow Wow made his debut as the lead role in Like Mike.
On August 10, 2013, via his official You Tube page, Bow Wow stated the reason that Underrated had been delayed was the result of raising his daughter and waiting until he was more mature; he also stated he planned on working on and releasing the album after he turned 28.
On June 24, 2014, Bow Wow announced via Instagram that after the 2014 BET Awards, he was going by his real name Shad Moss, claiming that he made a lot of history as Bow Wow and that it was now time for "the next chapter and challenge". I got a family I gotta provide for." On September 27, 2015, Bow Wow signed to Puff Daddy's record label Bad Boy Records.
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 first promo single being "For My Hood", featuring DJ Khaled & Sean Kingston.
On November 1, 2010, Bow Wow released his first promotional single from the album entitled "Ain't Thinkin' 'Bout You" featuring Chris Brown.
He later began to undertake lead roles in movies, such as Johnson Family Vacation in 2004 and Roll Bounce in 2005.
He also played a supporting role in the film The Fast and the Furious: Tokyo Drift in 2006.