If Jay-Z had his druthers, he would've never made it to his third LP.

It's been said time and time again that Hov originally planned to only record his debut Reasonable Doubt and then retire from the mic to run his Roc-A-Fella Records full-time. Sixteen years and 11 solo albums later, Jigga stands as rap's biggest draw and widely recognized greatest of all time. It was the Grammy Award-winning, five-time platinum Vol.2 ... Hard Knock Life which would ultimately catapult Jigga to superstar status.

"It was just so pure," Jay told MTV News of his most successful album to date.

Released 14 years ago today on September 29, 1998 (the same day as OutKast's Aquemini and A Tribe Called Quest's final LP The Love Movement), Hard Knock Life mixed Jay's newfound pop sensibilities with the unapologetic street gruff he'd been previously known for. And it was all spearheaded by the pain-stricken "Annie"-sampling title track.

"I feel like, that song, that record, that album took Jay to another level," former Roc-A-Fella recording artist DJ Clue told MTV News.

With dreams of rap retirement still looming over the head of the explosive rap star, Hard Knock Life started just like Hov's two previous LPs (Reasonable Doubt and In My Lifetime, Vol.1) with an opening skit by Roc-A-Fella funny guy Pain in Da Ass. Riffing off an Al Pacino monologue from his 1993 film "Carlito's Way," Pain helps Jay set the stage for his protégé Memphis Bleek. "I quit, I'm retiring," he says in a faux Pacino accent. "Ain't enough money in this game to keep me around."

It all made sense, except by the time track number two kicks in, that all-too-familiar"Annie tune," reworked into something for Ghettoville, U.S.A., it was clear Jay-Z was just too damn good to give it up. Hov knew it too, because on the closing bars of "Hard Knock Life" he had already changed his mind. "So I stretched the game out, etched ya name out/ Put Jigga on top and drop albums non-stop for ya n---a."

HKL may not get the same credit as the God MC's debut, or his 2001 classic The Blueprint, but over the course of 14 head-nodding tracks, the budding music mogul laid the groundwork for a rap career that seemingly has no end. While Vol. 2 will forever be marked by its singles ("Hard Knock Life," "Can I Get A..." and "N---a What, N---a Who"), it was the deep album tracks that anchored it to the streets. It was also no coincidence that it was the first time Jay had ever worked with his good pal Swizz Beatz, who was just a teen at the time.

"I wanted Dame Grease, 'cause he was workin' on the DMX album. I was like, 'Where's the guy that's making all of those songs?' " Jay said referencing the Harlem, New York, producer, who contributed the bulk of DMX's multiplatinum debut It's Dark And Hell Is Hot.

For whatever reason, Darrin "Dee" Dean, the Co-CEO of X's label, didn't link Jay with Grease, but instead tried to pawn his nephew Swizz off on Hov. Jigga could smell the nepotism a mile away, or so he thought. "I'm like, 'Nah don't try and play me with the nephew,' " Jay recalled of his mindset before he actually heard Swizz's beats. "He came in, he played those songs. We went from my office to the studio, we made four records ... From there, the body of the album was in place."

The records turned out to be the pessimistic and grim "If I Should Die," "Coming of Age (Da Sequel)" and the DMX-assisted "Money, Cash, Hoes." Jay and Swizz's fourth collaboration "Jigga My N---a" would appear a year later on Ruff Ryders' Ryde or Die, Vol. 1 compilation.

The sonic grit that defined Hard Knock Life was perfect for the time, but the album's depth is what makes it everlasting. On "Ride or Die," Jay sneakily dismantles then-rival Ma$e in one of rap's greatest subliminal dis tracks. "Reservoir Dogs," with its funky Issac Hayes sample remains an underground favorite and "A Week Ago" is a stark reminder of Jay's dark past before rap.

Go ahead, give it a spin. Fourteen years later, 14 tracks never sounded so good.

What is your favorite track off Jay-Z's Vol. 2... Hard Knock Life? Let us know in the comments!