Building a case for being the greatest rapper of all-time is largely predicated on one's accomplishments and longevity, two areas in which JAY-Z is near, if not at, the forefront.

Since first officially stepping onto the scene in 1996 with his classic debut album, Reasonable Doubt, the Brooklyn native has continuously risen to the occasion while leaving listeners in awe with his lyrical exploits and timely hits, putting together a resume that rivals his predecessors and offspring alike.

With more than 20 years and 13 solo studio albums under his belt, not to mention numerous collaborative endeavors and cutting-floor material, the sheer amount of defining moments in JAY-Z's career can seem overwhelming. But there are a few instances in the mogul's career that are synonymous with his continued evolution as an artist.

For instance, albums like Reasonable Doubt and In My Lifetime, Vol. 1 were the brainchild of a callous hustler attempting to reconcile his criminal with aspirations for stardom, resulting in some of his most edgy selections to date.

Vol. 2... Hard Knock Life would symbolize him realizing those aspirations, while subsequent albums would find him sneering at the competition while fulfilling his aspirations as a full-fledged boss, an evolution which was complete by the time Jay released what is often pitted against Reasonable Doubt as his best album 2001's, The Blueprint.

From there, retirements (The Black Album), comebacks (Kingdom Come), and sheer artistic license (American Gangster) were all themes that embodied the music featured on JAY-Z albums, making his career arc one of the more multi-faceted in the history of music.

To commemorate JAY-Z's legacy as one of the greatest emcees of all-time, The Boombox has handpicked and highlighted 11 of the most unforgettable songs in his career for your listening pleasure.

  • 1

    "Ain't No Nigga"

    JAY-Z featuring Foxy Brown

    When JAY-Z teamed up with fellow Brooklynite, Foxy Brown, on "Ain't No Nigga," the duo's contribution to The Nutty Professor soundtrack, his career began to take flight, with listeners intrigued by the relatively unknown spitter's slick flow. Hov has scored hits that have gone on to be more successful, but "Ain't No Nigga" represents his genesis as a rap star, and officially marked the arrival of Jigga.

  • 2

    "Brooklyn's Finest"

    JAY-Z featuring The Notorious B.I.G.

    Long before he would inherit the crown, JAY-Z struck a friendship with the original King of New York, The Notorious B.I.G., with the two gaining a mutual respect for one another, so much so that Biggie made an appearance on Hov's 1996 debut, Reasonable Doubt. Titled "Brooklyn's Finest," the Clark Kent-produced song saw the two trading bars championing their borough while pushing each other to their lyrical limits, making for a classic moment for hip-hop.

  • 3

    "Dead Presidents II"


    JAY-Z's catalog is littered with hits that rely more on his wit and charm than his prowess as a lyricist, but one of his finest performances to date lives on "Dead Presidents II," one of the singles released from Reasonable Doubt. Produced by Ski, "Dead Presidents II" is one of the songs responsible for cementing JAY's status as a top tier lyricist and one with the chops to evolve into a supreme soloist.

  • 4

    "Streets Is Watching"


    Depending on who you ask, In My Lifetime, Vol. 1 is either one of the more slept-on or maligned albums in JAY-Z's discography. But what cannot be denied is that it houses some of the hardest records of his career, one of them being "Streets Is Watching." Snarling at the peanut gallery and the opposition with every bar, JAY-Z is as cocksure as ever on this classic deep-cut.

  • 5

    "Where I'm From"


    After spreading love to the entirety of Brooklyn alongside the Notorious B.I.G., JAY-Z brings things close to home on the In My Lifetime, Vol. 1 gem "Where I'm From," taking listeners on a stroll through his stomping grounds in the Marcy Housing Projects. Famously throwing his own hat into the King of New York convo with the line "And argue about who's the best emcee, Biggie, Jay-Z, or Nas," Hov put forth an anthem that solidified Marcy Projects as a rap landmark, and the home of one of the greatest rappers of all-time.

  • 6

    "Hard Knock Life (Ghetto Anthem)"


    After failing to break through the glass ceiling of the upper echelon in mainstream rap with his first two albums, JAY-Z finally found his footing beyond regular rap fans with his third studio album, Vol. 2... Hard Knock Life. Released in 1998, Vol. 2... Hard Knock Life was led by the single "Hard Knock Life (Ghetto Anthem)," which would become JAY-Z's biggest hit at that point in his career, and push the album to five million in record sales.

  • 7

    "Big Pimpin'"

    JAY-Z featuring UGK

    Known for collaborating with artists from all over the country, JAY-Z surprised fans when he hooked up with southern rap duo UGK for "Big Pimpin'" off his Vol. 3... Life and Times of S. Carter album. Produced by Timbaland, the track featured a memorable opening verse by Hov, but was anchored with show-stealing verses on the part of his Texas counterparts, making it one of the more popular collaborations JAY-Z has ever recorded.

  • 8



    All is fair in love and war, but things got a bit personal between JAY-Z and Nas during their infamous war of words in the early aughts. The gauntlet was officially thrown on "Takeover," a scathing diss track on which Hov took aim at Nas and Prodigy of Mobb Deep. First teased at Hot 97's 2001 Summer Jam concert, the full-version of the track would arrive with the release of The Blueprint and be a pivotal moment in one of the greatest rap battles of all-time.

  • 9

    "99 Problems"


    Deciding to hang his jersey up with the release of his intended swan song, The Black Album, JAY-Z made sure that if he was gonna go out that it would be with a bang. Thus, he put together a collection of songs that speak to his genius as a songwriter and emcee. One song from the album that's indicative of his wizardry is the Rick Rubin-produced "99 Problems," which saw Hov firing back at critics and touching on racial profiling and discrimination, proving that he's equally effective over rollicking guitar riffs as he is standard boom-bap.

  • 10

    "Empire State of Mind"

    JAY-Z featuring Alicia Keys

    As one of the more legendary New Yorkers to call the Big Apple home, it was only right for JAY-Z to display his love and admiration for the five boroughs, which he does on The Blueprint 3 track "Empire State of Mind." Costarring alongside Alicia Keys, who contributes a powerful vocal performance, JAY-Z waxes poetic about what life in the big city is all about on the song, which won Best Rap/Sung Collaboration and Best Rap Song at the 53rd Annual Grammy Awards and is one of the most acclaimed songs in his stash of classic material.

  • 11

    "Story of O.J."


    Just when fans began to whisper that maybe he had lost a bit of the magic that made him one of the most beloved and feared rappers to ever step in a vocal booth, JAY-Z quieted any and all doubts with the release of 4:44, the rapper's 13th studio album, and first in nearly four years. While tracks like "Smile" and the album's title-track were both praised for their candor, one song from 4:44 that is particularly significant is "The Story of O.J.," which earned Hov a nomination for Record of the Year at 60th Annual Grammy Awards.