14. T.I. "I'm Illy" (2008)
T.I.'s "I'm Illy' isn't just a case for why T.I. is a great lyricist; it makes a case for why you can't reach your lyrical peak unless you write down your lyrics. Early in his career T.I. was dubbed "the Jay-Z of the South." A title he earned because, despite his heavy Southern drawl, Tip had enough wordplay to make his East Coast counterparts jealous. Yet, Tip rose to prominence in the 2000s after his debut I'm Serious dropped and he abandoned writing lyrics down. As Joe Budden once said, "More niggas said they didn't write down lyrics/The more it started to sound like they didn't," and on occasion flashes of Tip's lackadaisical output became apparent and all the more frustrating.
Right after getting caught with tons of guns and facing a hefty prison sentence, Tip went back to the pen and pad, a move that inspired his album's title, Paper Trail. Determined to prove that he hadn't lost any muster despite his legal cases, Tip hit the mic harder than Kobe hit the court after his rape trial.
"I'm Illy" is a typical rap song that isn't really about anything besides boasting, yet it addresses so many issues at once. Tip drops everyday boasts that could work on any rap song like, "Caked like Entenmann's, blowin' that celery/Stack that cash like the U.S. Treasury" and "You couldn't fuck with me with a Brazil hoe." He mixes that with exceptional multi-syllable rhymes, "Rarely out my element, barely out the ghetto with/One foot out and one foot in, intelligent as fellas get." But still finds time to touch on his legal troubles, "Of course this case lost all my endorsements." But the craziest part was, fresh off doing some real life gangsta shit, his threats like, "I'm out my fucking mind, need counseling/Please don't doubt me, trust me, drama ain't nothing/It's all fun and games 'til somebody start busting," felt way too true.
Still, it felt frustrating. After killing both of his verses, Tip assures at the end, "Just remember, I do this shit when I want to." Well why don't you want to do it more often? —Insanul Ahmed
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