The views expressed in this article are those of the author and do not necessarily reflect the official policy or position of any other agency, organization, employer or company.

Overnight success is often celebrated in the realm of rap, but many of the most impactful and influential artists endured years of rejection, setbacks and false starts before truly reaping the fruits of their labor. One artist familiar with having to wait their turn is JAY-Z, who many fans and critics deem as the greatest rapper of all time. His résumé may include a succession of platinum albums, hit singles and an endless amount of hardware celebrating his achievements, however, that wasn’t always the case. Prior to 1998, JAY-Z was considered to be a superior wordsmith and a worthy co-star alongside the likes of The Notorious B.I.G., Foxy Brown and Puff Daddy, but had yet to transcend the underground and fully emerge as a power player himself. Sure, Reasonable Doubt had struck a chord among rap aficionados and In My Lifetime…Vol. 1 may have yielded a minor hit or two, but neither earned Hov the cache that was afforded to peers like Ma$e, who was recognized as the brightest star in the New York City rap scene at that time and a mainstream darling.

However, the tide began to turn in 1998 when JAY-Z made a high-profile guest appearance alongside Jermaine Dupri on the single “Money Ain’t a Thang,” which dominated urban radio and was a Top 10 rap hit. But Hov’s buzz saw an uptick after the release of “Can I Get A…,” his contribution to the Rush Hour soundtrack and the lead single to his third studio album, Vol 2… Hard Knock Life. Released on September 29, 1998, Vol. 2 became JAY-Z’s first album to debut at No. 1 on the Billboard 200, selling over 350,000 units in its first week, a streak that has yet to be broken. In addition to “Can I Get A…,” the album was supported by the single “Hard Knock Life (Ghetto Anthem),” “Money, Cash, Hoes” and “Jigga What, Jigga Who (Originator 99),” all of which would be among the bigger rap hits of late 1998 and the first half of 1999. Topping out at over five million copies sold and earning the Grammy Award for Best Rap Album, Vol. 2 is universally regarded as JAY-Z’s most commercially successful album and considered a classic body of work.

Boasting guest appearances from DMX, Foxy Brown, Too $hort, Ja Rule, The LOX, Beanie Sigel, Memphis Bleek, Amil, Sauce Money, Big Jaz and Da Ranjahz, and a production line-up that consisted of boardsmen like DJ Premier, Timbaland, Swizz Beatz, Stevie J, Mark 45 King and others, Vol. 2 served as the moment when a number of rap fans were first introduced to JAY-Z and remains a landmark moment in his career.

In celebration of the album’s 21th anniversary, we dissected Vol. 2… Hard Knock Life and ranked the songs on the album from the least impressive to the most unforgettable. Where does your favorite stack up?

12 | “If I Should Die”

On “If I Should Die,” JAY-Z teams up with oft-forgotten Roc-A-Fella signees Da Ranjahz for a track on which all three rappers urge their crime partners to carry on tradition in their memory if they should perish before their time. Rhyming over a jittery backdrop provided by Swizz Beatz, Hov lists doing “joints with Mary J. Blige” as one of many accomplishments that leaves him at peace with fate, while Wais P and Haph contribute impassioned stanzas of their own, resulting in a bruising banger that may rank on the lower spectrum of Vol. 2, but speaks to the overall excellence of this breakout LP.

11 | “Ride or Die”

Jigga gets aggressive on “Ride or Die,” a track on which the Roc-A-Fella CEO wages war against rivals like Ma$e, with whom he was embroiled in a cold war during both New Yorkers’ rise to power. Dropping digs like “check your own videos, you’ll always be No. 2″—a reference to Bad Boy boss Puff Daddy’s “Can’t Nobody Hold Me Down” music video and Ma$e’s position as second fiddle in the label’s hierarchy—Hov adds insult to injury by recruiting Stevie J, a member of Bad Boy’s Hit-Men production stable, to craft the song’s instrumental, a testament to his attention for detail and mastery of the art of war.

10 | “Hand It Down”

No JAY-Z album is complete without an epic intro track, but unlike the majority of his other bodies of work, Vol. 2 features Memphis Bleek, Hov’s longtime understudy, attacking the DJ Premier-produced track instead of Hov himself, a surprise that proves pleasant as Bleek reels off one of the more high-powered verses in his catalog. Beginning with a monologue from Bleek’s own “Pain In Da Ass,” in which the comic appraises Bleek as a “new, improved JAY-Z,” “Hand It Down” may have been a premature coronation of the young protege’s ascension up the Roc-A-Fella ranks, but stands as a memorable moment from Vol. 2 that encapsulates the potential that made JAY, Dame and Biggs tap him as the unquestioned heir to the throne.

9 | “Paper Chase”

After working together on his first two albums, Reasonable Doubt and In My Lifetime, Vol. 1, JAY-Z and Foxy Brown team up once again on “Paper Chase,” a track on which the two have their mind on the money and nothing but green-backs and federal notes in their sight. Produced by Timbaland, “Paper Chase” would not only add to Foxy and Hov’s catalog of duets, but was also one of the first instances of JAY-Z working with Timbaland, who would become a frequent collaborator of his in the subsequent years.

8 | “It’s Like That”

“I might bark at X and spit at The LOX,” JAY-Z muses on “It’s Like That,” one of a number of one-liners that make this understated, DJ Kid Capri-produced number the strong close-out selection that it is. Powered by a sample of “Beggar’s Song” by Wet Willie and featuring additional vocals by Liz, “It’s Like That” is perhaps the most lyrically precise on Vol. 2 and captures Hov getting busy with a pair of rhyme spills that border on surgical, resulting in it being one of the more beloved deep cuts in the legend’s discography.

7 | “Can I Get A…”

JAY-Z urged listeners nationwide to get their bounce on with “Can I Get A…,” his contribution to the Rush Hour soundtrack and the lead single from _Vol 2 that helped his career to begin to truly take flight. Produced by Irv Gotti and Lil Rob, and featuring breakout performances from Amil and future superstar Ja Rule, “Can I Get A…” was one of the first instances of Hov making his sound more accessible to the mainstream, an adjustment that paid dividends, as the song would peak at No. 19 on the Billboard Hot 100 and reach platinum status, his first single to achieve that feat. However, in spite of being his first bonafide hit as the lead-artist, the album version of “Can I Get A…” falls a bit short of the radio edit, resulting in it ranking as a middling track on JAY-Z’s most successful album to date, while being one of its most recognizable tracks.

6 | “A Week Ago”

Brooklyn connects with the Bay Area when JAY-Z and Too $hort match wits on “A Week Ago,” one of the more high-powered collaborations on Vol. 2 and a selection on which Hov flexes his storytelling skills. Spinning a parable of a hustler-turned-informant attempting to turncoat on his co-conspirators, Hov goes in over a sample of the Isley Brothers’ “Ballad of the Fallen Soldier,” while Too $hort handles hook duties and closes out the track with a few words of his own.

5 | “Coming of Age (Da Sequel)”

“I done came up, put my life on the line / Shook the game up, now it’s my time to shine,” Memphis Bleek proclaims on “Coming of Age (The Sequel),” a track that picks up where the pair left off on Reasonable Doubt and stands as another torch-passing moment between the two Marcy heavyweights. Produced by Swizz Beatz, “Coming of Age (The Sequel)” is set around Hov and Bleek’s increasingly strained relationship and the neophyte’s quiet desire to become the head of the operation and reap the benefits that are afforded a crime boss. However, when the smoke clears, Memphis Bleek shirks his jealousy and reaffirms his allegiance to his mentor on what is a worthy sequel to the original and is one of Vol. 2‘s most riveting compositions.

4 | “Nigga What, Nigga Who (Originator 99)”

One of two productions he’s credited with on Vol. 2, Timbaland’s fingerprints are all over “Nigga What, Nigga Who (Originator 99),” an uptempo selection from the album that finds JAY-Z employing a double-time flow over jittery drums and synths, and turning in a masterful lyrical performance in the process. Featuring a guest spot from Amil, who urges Hov to “switch your flow” and get his dough, and former mentor Big Jaz, who reels off a climatic stanza to anchor the track, “Nigga What, Nigga Who (Originator 99)” was released as the fourth and final single from the album and stands as a prime display of Hov’s wizardry as an emcee, making it an essential selection.

3 | “Reservoir Dogs”

No album from the late 90s was complete without a posse cut on which a rapper tested his mettle against the top spitters in the game. Being the competitor that he is, JAY-Z reveled in the opportunity to run such a gauntlet, recruiting The LOX, Beanie Sigel and Sauce Money to spar with him on “Reservoir Dogs,” a track that will leave any rap enthusiast drooling at the mouth with the amount of metaphors and punchlines volleyed back and forth between the six emcees. Produced by Rockwilder, “Reservoir Dogs” is a lyrical free-for-all that hits on all cylinders and is a reminder of the brutal field of spitters that inhabited the East Coast rap scene during one of its renaissance periods.

2 | “Money, Cash, Hoes”

Holding the title of King of New York was once the most prestigious honor one could be bestowed in rap and, in 1998, both JAY-Z and DMX were leading contenders to occupy that throne, which was left vacant the previous year in the wake of The Notorious B.I.G.’s death. And with a history that includes a legendary rap battle, as well as various run-ins on wax, the stage was set for the two to collide for the world to witness, which occurred on Vol. 2 when JAY-Z tapped DMX to appear on “Money, Cash, Hoes,” a track from the album that cast the two titans of NYC opposite each other, over production by Swizz Beatz. With Swizz going ham on the Casio, Hov and X turn in more complimentary performances instead of going toe-to-toe in an effort to outshine each other, with each artist vibing off of the other’s energy, helping make “Money, Cash, Hoes” one of the biggest street anthems of 1998 and spawning an even more explosive remix the following year.

1 | “Hard Knock Life (Ghetto Anthem)”

Prior to the release of Vol. 2, JAY-Z had already proved himself as an elite wordsmith and collaborator with the ability to coexist with the likes of The Notorious B.I.G., but still had yet to establish himself as a hitmaker or household name. While the tide surrounding his status and reputation began to change with the release of singles like Jermaine Dupri’s “Money Ain’t a Thang” and Vol 2.‘s lead single “Can I Get A…,” the song that would truly break down the glass ceiling between him and widespread mainstream success was title track “Hard Knock Life (Ghetto Anthem).” Produced by Mark The 45 King, “Hard Knock Life” captured JAY-Z speaking to the heart of the hood over an Annie sample and using his own experience and come-up in an attempt to help inspire the next generation of hustlers to overcome their obstacles and prevail in the game of life. Released as the second single from Vol. 2, “Hard Knock Life” would be JAY-Z’s most successful at that point in his career, peaking at No. 15 on the Billboard Hot 100 and helping push Vol. 2 to over 5 million copies sold in the U.S. alone, making it one of the biggest rap songs of the entire year, and the most unforgettable song from the most successful album in the most accomplished rapper’s career.

More by Preezy Brown: