In 2000, she became the first artist signed to Clive Davis` J Records. Her self-titled debut album Olivia was released in 2001 and featured the singles "Bizounce", "R U Capable", and "You Got the Damn Thing". The album was heavily underpromoted, so she left J Records. She parted from the label because she felt they were not promoting her enough, and forcing her into the bad girl image. The album sold under 100,000 copies. The album debuted at number fifty-five, selling 16,527 copies in the first week. It fell off in just four weeks.

In 2004, Olivia re-emerged as the first woman signed to G-Unit Records. She has contributed vocals to the trio`s debut album Beg for Mercy and to 50 Cent`s The Massacre, including that album`s number-one single "Candy Shop".

Her first solo single released via G-Unit Records was "Twist It", featuring fellow G-Unit member Lloyd Banks, followed up by "So Sexy" in summer 2005. As both songs to chart, Olivia briefly attended Hofstra University in New York after releasing her sophomore album, Behind Closed Doors, which is now slated for a 2007 release on Interscope and G-Unit Records. Around the same time Olivia also contributed vocals Shaggy`s single "Wild 2Nite".

In Fall 2005, it was rumored that 50 Cent and G-Unit Records might have dropped the singer from the label (due to poor reception by the public) and considered replacing her with singer Keyshia Cole. However, these rumors were found to be inaccurate after Olivia announced on Sirius satellite station Shade 45 that she was not leaving G-Unit Records.

Olivia released her third single, "Best Friend" featuring 50 Cent, in 2005.

On January 7, 2007, a new Olivia song titled "My Daddy" was leaked to the internet. It was produced by J.R. Rotem.

In Spring 2007, Olivia was dropped from G-Unit. This was confirmed by 50 Cent himself during an April 4, 2007 interview with Miss Jones on Hot 97. 50 Cent also confirmed this with an interview with BBC 1Xtra DJ Semtex, saying it was due to miscommunication rather than talent.[citation needed]

Olivia has resently sign a new deal with Def Jam Records

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