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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.As of September 27, 2015, Bow Wow had officially been signed to a new label, Bad Boy Records, which is owned by Puff Daddy.Bow Wow made his first movie appearance in All About the Benjamins, in 2002 as a cameo.He also played a supporting role in the film The Fast and the Furious: Tokyo Drift in 2006.Bow Wow also appeared in five episodes of the television series Entourage. Everything is just 'Bow Wow,' no 'Lil' Bow Wow.'" The first album released under his new name was Unleashed in 2003.In the same year, Bow Wow made his debut as the lead role in Like Mike.

Not here for always being linked to the 29 year old, Cole decided to address it once and for all. "@keyshiacole check this out blood i don't got nothing to do wit what ever you got going on 4 you to egg my car, keep me out the bullshit," he wrote. The album was intended to feature with Birdman, Boyz II Men, Chris Brown, DJ Khaled, Fabolous, Game, Lil Wayne, Lloyd Banks, Meek Mill, Nas, Nelly, Sean Kingston, Snoop Dogg, DMX, Styles P and Talib Kweli.The first promo single being "For My Hood", featuring DJ Khaled & Sean Kingston.Its debut single was "Bounce with Me", which featured R&B girl group Xscape. The next single, "Like You", featuring Ciara, coincided with the beginning of Bow Wow's relationship with the singer.The album also included "Bow Wow (That's My Name)" featuring Snoop Dogg, which topped the rap chart, In 2002, his second album Doggy Bag was released with singles "Take Ya Home" which peaked at #72 on the Hot 100 and #21 on the Hot R&B/Hip-Hop Songs chart, and "Thank You" with Jagged Edge, #1 on the R&B chart. New Jack City II, his sixth album, was released in March 2009 and his first album to include a Parental Advisory: Steven Roberts of MTV News observed that this album explored "the influence of crack cocaine in inner-city communities" and featured such guests as T. Three promo singles were released in late 2008: "Marco Polo" featuring Soulja Boy, "Big Girls", and "Roc The Mic".

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On November 1, 2010, Bow Wow released his first promotional single from the album entitled "Ain't Thinkin' 'Bout You" featuring Chris Brown.

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