Throughout her career, Jacki-O has worked with high-profile artists including Timbaland, Busta Rhymes, T-Pain, Ghostface Killah, Ying Yang Twins and DJ Khaled.
As she got older, she became known for committing credit card fraud and stealing items from stores to resell at half price - which she frequently discussed in her music.
In 2008, Jacki-O revealed to Hip Hop Weekly that she was forced to have sex with a Poe Boy Entertainment executive to receive a $10,000 advance that she was previously promised.
After the interview garnered negative comments, Jacki-O explained that she was not proud of what occurred, but wanted to come forward about abuse she endured in the industry.
"[13] 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".
[14] Her next mixtape, released four 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".
[15] In 2014, Jacki-O announced via her official Facebook account that she transitioned from Gangsta rap to Christian hip hop due to religious commitment, stating that she has been "touched by God" and that she will release her next album when the timing is right.
[17] She released her autobiography, Relentless in 2010, which detailed her life growing up in Miami, Haitian background, rise to fame as a rapper, and her charity work with people with disabilities.
[25] Although Jacki-O gave DJ Khaled a positive shoutout in her 2004 mixtape The Official Bootleg, she claimed that he did not truly support Miami rappers in a 2010 interview with XXL Mag.
[27] In January 2006, in an attempt to break her recording contract with Poe Boy Entertainment, Jacki-O filed for Chapter 7 bankruptcy - declaring debts of $144,225 and assets of $1,340.
[30] In a 2008 interview with Hip Hop Weekly magazine, Jacki-O claimed that she was forced to have sex with a Poe Boy Entertainment executive to receive a $10,000 advance that she was previously promised.