By Séamus Smyth

5. Guns and Roses

Heavy D on production, Lenny Kravitz on the hook and Hova on the mic, “Guns N Roses,” is a musical red carpet. The title itself is a clear reference to Notorious B.I.G’s line “more guns than roses,” and Jay takes full advantage of his homeboy’s memorable quip, even stealing the line on the second verse. It would become the beginning of Jay’s experimentation with rock music, which climaxed when he paired with Linkin Park on “Collision Course,” and of course when he released the number one track on this list.

4. Dead Presidents II

He sampled his future enemy Nasty Nas on this ridiculously-grimy track from his debut album, “Reasonable Doubt.” This hypnotic sensation is a different version of Jigga. The gold bottles, the yachts, the Grammy’s are in a different dimension at this point in time. This is Hova the crack dealer desperately trying to turn his strung-out poetry into legitimate dead presidents. Jay isn’t scared, hell he seems to embrace the drug dealer lifestyle, but he can’t help but strive for a more admirable lifestyle. This song removed any doubt that H to the Izzo would become a staple of hip-hop music and not the street corner.

3. A Week Ago

What makes Jigga so talented is his ability to condense a book-length story into a thugged-out nightmare. “A Week Ago” is discussing how Jay managed to abate the police while his partner in crime wasn’t as fortunate. His comrade becomes increasingly sour over their drastically different circumstances and Jay serves the reality to him cold. Jay has often used an oriental-style beat to convey his more serious convos, just as he does on this cut from “Vol.2..Hard Knock Life.” Too $hort is notorious for spitting strictly about women and sex, yet Jay manages to convince him to lay down easily his sickest guest appearance of his career. Similar to how the Beatles’ pondered about the innocence of “Yesterday,” Jay reminisces about how life was all good just “a week ago.”

2. Renegade

It was the two most powerful rappers at the time making arguably one of the most profound rap songs of all time. The two could have recruited any producer of their choosing and released a pop-friendly radio blockbuster, but decided to address not only their haters, but society as a whole. Jay-Z and Eminem, both incredible wordsmiths in their own right, showed up to the studio with enough venom to compete with a family of cobras when they recorded this legendary duet.

1. 99 Problems

He has 99 problems yet the most significant one seems to be that he is constantly butting heads with passive racists. He’s pulled over for barely exceeding the speed limit and is written off by critics who insist he raps strictly about “Money, Cash, Hoes.” Of course these ignoramuses clearly don’t “understand the intelligence that Jay-Z has,” as he has managed to escape any serious repercussions from the arms of the law or the wrists of journalists. No one has ever camouflaged their boasting about dating one of the most beautiful women in the world than Jay-Z has. The 99 problems predicament is one all his listeners can relate to, but the “bitch ain’t one,” is a grandiose under-statement. He has more issues to cope with than a doctor’s textbook, yet his trademark grin remains intact. Why? Because after a strenuous day of being pulled over by police and crucified by magazines, he has Beyoncé Knowles waiting for him in the jacuzzi.