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Chingy's debut album Jackpot was released on July 15, 2003 on Disturbing tha Peace.Unable to secure a distribution deal through Def Jam, Ludacris negotiated a deal to distribute the album through Capitol Records. Within a year of the release of Jackpot, It was certified Platinum by the RIAA.Kelly, Bun B, Lil Wayne, Lil Flip, Janet Jackson, David Banner, Nate Dogg, and Get It Boyz.Powerballin' sold over one million copies and received a Platinum certification by the RIAA on March 21, 2005. Louis, Missouri rapper Chingy was accused of having relations with Sidney Starr, a transgender model. Cause it was so much bad publicity around it…I’ve never been through a sabotage situation like that. The promoter had some girl dancers on stage that were dressed in body paint. They were promoting whatever he wanted them to promote. And during an interview with Vlad TV, Chingy revealed that rumors of his relationship with Sidney Starr injured his music career and resulted in the loss of his record deal due to the negative publicity. They just had this person’s lie…It actually, it injured my career a little bit. And it was so fabricated and false.” Prior to speaking on the backlash, which resulted from Sidney Starr’s rumors, Chingy recalled meeting the model/backup dancer at a show with Ludacris in Chicago. And one who I thought was a young lady that came up to me that wanted a picture—I just took the picture.

“I would have [said], ‘Hold up, I ain’t [about to] do this shit, no you do it and I’m just going to not say nothing and deny it.’ I was definitely not in the right mindset at that time in my life.Guest appearances included Ludacris, Snoop Dogg, Murphy Lee, I-20, Raindrop, Tity Boi of Playaz Circle, Trina, and Jermaine Dupri. Chingy released his second album, Powerballin', on November 16, 2004 through Slot-A-Lot Records and Capitol Records.