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On September 30, 2008, the world would receive T.I.’s sixth studio album, Paper Trail. While serving a house arrest and awaiting his one-year sentence (after pleading guilty to possessing illegal firearms as a previously convicted felon), T.I. crafted the lyrics and album’s concept. Of course, Paper Trail would mark a brief going-away party of sorts, but it also solidified Clifford Harris as the King of Trap he claimed to be since his second album, 2003’s Trap Muzik.

At the time of Paper Trail’s release, it had been undeniable how much the Dirty South controlled the airwaves and ran hip-hop. Still, that didn’t prevent some in the hip-hop community from not taking trap music—a genre that T.I. officially coined—seriously. The 2007 to 2009 stretch became a period of rap history where the three titans utilized varying approaches to make sure their native sound stayed in the forefront. Lil Wayne embraced Auto-Tune while leaning in a more mafioso direction—as evident by Tha Carter III’s album cover of his baby picture photoshopped with face tatts and a gray suit blazer. Jeezy (who, back then, still had the “Young” moniker) decided to have political conversations on The Recession. But T.I., on the other hand, turned trap music more… pop.

From the start of Paper Trail, the intention to have his sound of trap doused with pop cadences is very clear. On the DJ Toomp-produced “56 Bars (Intro),” T.I. commences the album with a cocky speech. “Aight Toomp, man, this what the folks been waiting on I guess,” declares the recording artist; later on asking, “Aye man, they been waiting on this shit since ‘What You Know,’ huh?” Coincidentally, “What You Know” was the highest charting single of T.I.’s career since its release two years prior, reaching a No. 3 peak on the Billboard Hot 100 and topping the rap charts. “56 Bars (Intro)” contained the hard-hitting bass and marching band sound that propelled ATL trap to the forefront of the hip-hop soundscape, but something about it seemed a bit more polished. Better yet, regal.

In fact, all of Paper Trail had a bit of lightness to it, perfectly suited for radio. The LP produced eight singles stretching from the release of “No Matter What” on April 29, 2008 until the collaboration with Justin Timberlake, entitled “Dead and Gone,” ran its full course during the first quarter of the 2009 music calendar. Although it’s the seventh track on Paper Trail, “No Matter What” served as the perfect precursor for T.I.’s sixth era, as he announces “still I stand” to what is a triumphant march to the bass. In the opening lines, “Never have you seen in your lifetime / A more divine southern rapper with a swag like mine,” he alludes to what makes him stand apart from the competition. He’d then go on to rap about serving time, criticizing blogs and gossip magazines reporting that that would be until 2027.

The narrative on Paper Trail wasn’t all about rising above his pending sentencing. After all, T.I. had been on a mission to build up his musical legacy and fortunes, utilizing as much time as he could to master a slew of hits beforehand. His second single, “Whatever You Like,” not only took the summer by storm, it peaked at the summit position of the Billboard Hot 100, becoming Tip’s first solo track to do so. Promising his love interest the finest things in life, such as “stacks on deck, Patron on ice”—because “I want yo body, need yo body”—T.I. became more debonair with his sound. Singing on the hook, the King of the South followed the lover’s crooning path that propelled Lil Wayne’s “Lollipop” to the same spot on the charts earlier that year. In terms of Paper Trail deep cuts that follow suit, the Usher-featuring “My Life Your Entertainment” and “Porn Star” allude to paparazzi chases and media’s infatuation with T.I.’s life. It became clear that this new attitude centered on pop’s acknowledgment of trap’s top tier.

The era continued with singles designed for the streets, but not necessarily the top position of the charts. “Swing Ya Rag” closed in at No. 62, despite having a Swizz Beatz track that matched T.I.’s earlier sound: a happy medium between the rowdy energy of Urban Legend’s “Bring Em Out” and the clapping beat of King’s “Get It,” all produced by Swizz himself. “What’s Up, What’s Haapnin’?” didn’t do any better at No. 84, as it became apparent the Shawty Lo-diss track repeatedly calling him a “hater” didn’t land, despite having a Drumma Boy beat. The streak of out-the-Top-40 would end with the release of “Swagga Like Us.”

“Swagga Like Us” came as an epic proportion to hip-hop. At the time, it was one of the rare moments where all of game’s goliaths would collab on a track, forming a supergroup just for one song. Featuring Kanye West, JAY-Z, and Lil Wayne—with a clever sample of M.I.A.’s hit song “Paper Planes”—“Swagga Like Us” alerted the contemporary about who had arguably been running rap for the past couple of years. It’d only make sense that the four rap artists that continuously boast about their swag would each get the chance to finalize their case with top-notch co-signers. “No one on the corner has swagga like us, swagga like us, swagga swagga like us” would ring truest, and all the way to the No. 5 position of the Hot 100.

The follow-up single, “Ready For Whatever,” played as an autobiographical choice, where T.I. muses about being “a father to my son” and people wanting to stop his bag while he climbs to the top. This would be the narrative that T.I. continues much into his later discography, particularly on 2014’s Paperwork. However, the standout moment of the era would be the next single, “Live Your Life.”

“Live Your Life” ended up leaking on the internet more than a week before its official debut in the public conscience at the 2008 MTV Video Music Awards. On that September night, viewers not only experienced T.I. serenading a model to “Whatever You Like,” but in the middle of the performance, T.I. emerges from a convertible, quickly changing out of his blazer and button-down to reveal a look resembling his Trap Muzik days. But the star of “Live Your Life” wasn’t exactly T.I. Rising from underneath the stage, Rihanna stole the show with her all-black look of a crop top, motorcycle jacket and stunna shades. This moment would be a precursor to Rih’s Rated R persona and one of her most defining features to date.

“Live Your Life” represented the spirit of Paper Trail. Knowing all of his legal troubles, T.I. mastered an anthem for, as Rihanna puts it on her extended album verse, “do[ing] it how I wanna do.” The song accurately captures an important message: “I’m the opposite of moderate, immaculately polished with / The spirit of a hustler and the swagger of a college kid / Allergic to the counterfeit, impartial to the politics / Articulate, but still I’ll grab a nigga by the collar quick.” T.I. would also go on to note his mainstream status: “Whoever havin’ problems with their record sales, just holler Tip.” What sold the public most about “Live Your Life,” however, was the infectious sample of O-Zone’s 2004 song “Dragostea Din Tei,” a.k.a the “Ma Ya Hi” song.

Closing out the Paper Trail era, “Dead and Gone” merged adult contemporary pop with rap—being the first case of “See You Again” before Charlie Puth and Wiz Khalifa would make that a tribute hit in 2015. Dedicated to his slain bodyguard Big Phil, “Dead and Gone” missed the top position by one spot, while also being nominated for two rap category Grammys. Although this didn’t best their previous collab, 2006’s “My Love,” “Dead and Gone” still remains a signature for both T.I. and Justin Timberlake today.

As “Dead and Gone” finalized its run, so did the Paper Trail era. In March 2009, T.I. was sentenced to one year and a day, starting in May of that year. Unfortunately, after his release he’d find his way back to another stint, for a different stem of charges. Despite all of this, T.I. proved that through trying times comes success if you stay authentic to your persona.

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