On this day, Sept. 30, in hip-hop history... 

Grand Hustle/Atlantic Records
Grand Hustle/Atlantic Records

2008: A year after dropping T.I. vs. T.I.P. to mixed reviews, T.I. released Paper Trail, his sixth studio album and arguably his best body of work to date. As he began working on the 16-track project, the Atlanta native faced a multitude of hardships in his personal life. While still mourning the loss of his best friend and bodyguard, Philant, T.I. was also awaiting trial for federal weapons and possessions charges, for which he would later serve prison time. These adversities resulted in some of the best music T.I. has ever made, as Paper Trail went on to earn double-platinum status and land four singles in the top five of the Billboard Hot 100.

Throughout the album, Tip addressed many of the issues that he was dealing with at the time. On track three, "Ready For Whatever," he explained the dilemma he was in prior to the weapons charges: "Now is it that hard to understand if you listen/Either die or go to jail, that's a hell of a decision/But I'm wrong and I know it my excuses ain't important/I'm just tryna let you know that I ain't think I had a choice." On "Dead And Gone" — a track that could be heard non-stop on every radio station in 2008 — T.I. described the heartbreak he experienced after the death of Philant, along with help from Justin Timberlake on the hook.

He links up with fellow A-Town stars Ludacris and B.o.B for one of the best songs production-wise from the album with "On Top Of The World." And classics like "Live Your Life" and "Swagger Like Us" will stand the test of time, forever cemented as a part of Clifford Harris Jr.'s musical legacy. When discussing the best hip-hop albums of the 2000s decade, Paper Trail should definitely be in the discussion. —Eli Schwadron

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