Pablo may have catapulted to stardom overnight, but he labored for years before getting his big break. Born in Greensville, NC, he eventually moved to New York when he became serious about breaking into the rap game. There, he managed to befriend such luminary figures as Busta Rhymes, Mystikal, and Black Rob. His recorded debut came on a remix of the latter's "Whoa!," which caught the attention of many, including Timbaland. Then, while at a club in New York, Jive's head of A&R happened to hear Pablo dropping some rhymes with Black Rob, and subsequently signed him to a contract. Jive then gave Pablo a chance to shine on Mystikal's Let's Get Ready album, while, around this same time, Missy Elliott introduced Pablo to Timbaland, who had been curious about the rapper ever since hearing him on the "Whoa!" remix. Jive made the collaboration happen, and the label found itself with a sure-fire debut single, "Raise Up."

"Raise Up" first began getting airplay in late summer 2001, beginning in the South and spreading like a virus from there. It wasn't long before the video was all over MTV and the song was creeping up the Billboard charts. Eventually peaking at number 25 pop and number nine R&B, "Raise Up" remained on the charts for months and set the stage for Diary of a Sinner, Pablo's debut album. The album featured three Timbaland tracks as well as productions by Prophecy, Chucky Madness, Abnormal, and Pablo himself. Not surprisingly, it sold many, many copies, making Pablo another of the overnight superstars produced by the early-2000s Dirty South boom.

But then not much came of Pablo. Diary of a Sinner failed to spawn a follow-up single of much magnitude, and Pablo made very few guest appearances. Jive scheduled his sophomore album for late 2002 but then pushed it back indefinitely. It wouldn't be until mid-2004 that Jive finally released Still Writing in My Diary: 2nd Entry, by which point a great many rap listeners had forgotten about Pablo. The album's lead single, "Freek-a-Leek," did its job well, however. Produced by the then red-hot Lil Jon, the sexually explicit song was successful in many ways: it returned Pablo to the upper reaches of the Billboard charts; garnered endless play on urban radio and music television; crossed over well to the female audience; became a club favorite overnight; and perked interest for the long-delayed Still Writing in My Diary.