In 1999 Jacki teamed up with PoE Boy Entertainment to obtain a recording contract; in the process, she released her first mixtape, entitled The Official Bootlegg. It went on to sell over 70,000 copies and was downloaded over 200,000 times. Subsequently, she released her first music video, "Nookie", which became her biggest hit to date.
In 2004, Jacki-O was signed to TVT Records, whereupon she released another music video, "Fine", (featuring the Ying Yang Twins), as well as two more singles, "Slow Down" and "Sugar Walls". Her debut album, Poe Little Rich Girl, was released October 26, 2004, selling 11,181 in it's first week. The next year, she filed for bankruptcy, reportedly to be released from her contract with TVT Records and Poe Boy Entertainment. In late 2006, Jacki-O released her second mixtape, entitled Free Agent.
Her next mixtape, released two years later in 2008, was entitled Jack-Da Rippa and featured the singles "I Got Yo Man", "3rd Eye", "Cool It Now" and "Queen Of The South". This led to a recording contract with her own label imprint Jackmove Ent. the next year, where she released Lil Red Riding Hood, featuring her newest single, "Baby Mama", as the lead-off track. Following this, she released a mixtape entitled BBBP (Bad Bitches Bang Pink).
In March 2010, Jacki-O announced that she is gearing
up for the release of a new street album/mixtape, titled Griselda
Blanco, which she plans to release digitally.
Jacki-O's first novel is called Grown & Gangsta
(2008), an "urban tale". She is currently working on an autobiography called Relentless (est. 2010),
in which she will "detail her life growing up in Miami, her rise to fame as a rapper, and her charity
work with people with disabilities."
Released: October 26, 2004 on Poe Boy/TVT Records
Released: March 10, 2009 on Jack Move/Gracie/EMI
Released: 2004 on Poe Boy
Released: 2006 on Jack Move Entertainment
Released: 2008 on Jack Move Entertainment
Released: 2009 on Jack Move Entertainment
Released: 2010 on Jack Move Entertainment
Year Song Top 100 Hot R&B
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