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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.
Bow Wow dropped the "Lil'" from his stage name in April 2002; he told MTV News: "I changed my name because I'm getting older now and it's too many Lil's. The first official single, "You Can Get It All" featuring Johnta Austin, samples TLC's "Baby-Baby-Baby" and peaked at #55 on the Hot 100 and #9 on the Hot Rap Tracks.
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 reference of him working on his new album Underrated and it is already in production.
The first promo single being "For My Hood", featuring DJ Khaled & Sean Kingston.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 planned to release his new then-titled album Underrated on Cash Money Records, but the record underwent a number of delays and in mid-November 2011, Bow Wow announced on his blog that the record wouldn't be out before 2012.Since he brought me in the game, its only right i involve him and end it with him. NOBODY SAFE #DPG #ATK THE TITLE OF MY FINAL ALBUM "NYLTH" @rmmpercy @dazdillinger @snoopdogg A photo posted by Bow wow (@shadmoss) on Not for nothing, but this is the second time Bow Wow has announced his retirement, following on the heels of a 2009 interview in which he said he was hanging it up.
"There's nothing more that I want to accomplish," he said back then at age 22.
On October 24, 2011, Bow Wow released the single entitled "Sweat" featuring Lil Wayne, and though it was thought to be the first official single from the album it was also dubbed by Bow Wow as a promotional single.