To be a great emcee, one must not only be able to string together sentences that end in a rhyme, but also have the skill to paint a picture for the listener.

In hip-hop, the storyteller is often held on a pedestal, with many of rap's all-time greats having transferred various plots and themes onto wax throughout the years. While there have been a slew of notable rappers that have mastered the art of storytelling, one that ranks near the top of the list is The Notorious B.I.G., who, in spite of his relatively short catalog, is often regarded as the greatest rapper of all-time.

Infamous for his wit, charm and charisma, the late Brooklyn rapper's ability to spin spellbinding tales was apparent from the outset of his career, particularly on the early singles "Party and Bullshit" and "Dreams." Both songs pushed the envelope and got the attention of the underground prior to his major label debut.

But it would be his rags-to-riches parable on Ready to Die's lead-single, "Juicy," that would truly cement him as a new star and place him on the fast-track to becoming the King of New York.

One aspect of Biggie's storytelling that set him apart from many of his contemporaries was the colorful characters he wove into his verses. His knack for detail gave the characters he mentioned backstories and personas of their own.

On Ready to Die and Life After Death, the two albums he recorded prior to his murder in 1997, The Notorious B.I.G. introduced listeners to a cast of fictional figures that have been immortalized in hip-hop—a wrinkle in the fabric of his influence on hip-hop, but an essential one.

From Pops From The Barbershop to Dark Skin Jermaine, The Boombox presents our ranking of the Top 10 fictional characters from The Notorious B.I.G.'s catalog.

  • 10

    "Miss U" featuring 112


    "There was this girl around the way that made cats drool/Her name's Drew, played fools out they money in pool/People swore we was fuckin', but we was just cool/She used to hang while I slang my joints after school"

    The Notorious B.I.G. introduces us to Drew, an around-the-way girl and kindred spirit with whom the Bed Stuy legend shared a special bond. Unfortunately, Drew would get mixed-up with a crew of wholesale drug dealers and be murdered by Taya, one of her lovers' baby mothers, in a jealous rage, making her character one of the more cautionary to be introduced to us by The Notorious B.I.G.

  • 9

    "Somebody Gotta Die"


    "I'm interrupted by a doorbell, 3:52 - who the hell is this?/I gets up quick, cocks my shit/Stop the dogs from barking, then proceed to walking/It's a face that I seen before/My nigga Sing, we used to sling on the 16th floor"

    Sitting in his plush crib on a rainy night, The Notorious B.I.G. gets a visit from Sing, an old associate he met while the two were hustling hand-to-hand, who has some unfortunate news about their mutual friend C-Rock, who was the victim of a murder earlier that night. After hipping Biggie to the whereabouts of C-Rock's murderer, Sing directs him to where the culprit and his crew holds court. Biggie gets retribution for the murder of his friend, albeit with a unexpected twist.

  • 8

    "Nasty Boy"


    "I remember we went to Tennessee/Then we came home, mad messages was on my phone/Bitch named Simone/Screamin, she fiendin for the semen"

    Returning to Brooklyn following an excursion below the Mason-Dixon, Biggie makes a booty call to Simone, a half black, half Indian beauty who's been blowing up his answering machine in hopes of setting up a rendevous. Being the player that he is, the Brooklyn Don obliges, bringing out the whipped cream, ice, and handcuffs after taking her back to his condo for a night of pleasure.

  • 7

    "Somebody Gotta Die"


    "Filling clips, he explained our situation/Precisely, so we know exactly what we facing/Some kid named Jason in a Honda station wagon/Was bragging, about how much loot and crack he stacking"

    Jason, the leader of a murderous drug crew in Brooklyn, gets in Biggie's cross-hairs after it's discovered that he's the cause of the murder of Biggie's close friend C-Rock. The irony in this tale is deep, as Jason targeted C-Rock for his participation in a robbery that resulted in Jason's family being harmed. However, The Notorious One plays judge and jury, murdering Jason, who was holding his daughter at the time of his death, in cold blood, settling the score once and for all and making it an eye for an eye.

  • 6

    "You're Nobody (Til Somebody Kills You)"

    Tamika and Tammy

    "Incidents like this I take trips/Lay up in Miami with Tamika and Tammy/Some Creole C-O bitches I met on tour/Push a peach Legend Coupe, gold teeth galore"

    Tamika and Tammy, two Creole correctional officers based in Miami, link up with The Notorious B.I.G. during a tour-run and proceed to put him onto some of the finer things in life. Meeting up with Biggie in his own stomping grounds, Tamika and Tammy stay true to their word, gifting him to gator shoes, putting him onto Cristal, and moving throughout the five boroughs with ease.

  • 5

    "Niggas Bleed"

    Puerto Rican Gloria

    "We agreed to go in shooting is silly/Because niggas could be hiding in showers with Mac-millis/So I freaked them, the telly manager was Puerto Rican/Gloria, from Astoria"

    As chance has it, Frank White spots Gloria, a boriqua from Astoria, who happens to be working as the manager at the hotel that he and his partner Arizona Ron are meeting for a phony drug transaction. Gloria, who used to run with some of Biggie's rivals in the early '90s, gives Biggie intel on a Jamaican and two lesbians that have been parked outside in a Range Rover. The informationproves to be invaluable when all is said and done.

  • 4

    "Everyday Struggle"


    "I had the master plan/I'm in the caravan on my way to Maryland, with my man Two-TEC's to take over this projects/They call him Two-TEC's, he tote two TEC's/And when he start to bust, he like to ask, "Who's next?"

    After realizing that the crack economy was booming outside the five boroughs of New York City, The Notorious B.I.G. takes a trip down to the home of the Terrapins, accompanied by his partner Two-Techs, a trigger-happy goon out of Brooklyn. Two-Techs and The Notorious B.I.G. would eventually go their separate ways shortly before Two-Techs was murdered in a small town during a gun-trafficking transaction gone awry.

  • 3

    "You're Nobody (Til Somebody Kills You)"

    Dark Skin Jermaine

    "You mean that kid that nearly lost half his brain over two bricks of cocaine?/Getting his dick sucked by Crackhead Lorraine?/A fucking shame, dude's the lame, what's his name?/Darkskin Jermaine, see what I mean?"

    On the Life After Death outro "You're Nobody (Til Somebody Kills You)," The Notorious B.I.G. reminisces on a Brooklyn hustler named Jermaine that met his demise on the very blocks he plied his trade on. From the Champagne Range to the Gucci frame, Dark Skinned Jermaine seemed to be on top of his game, but would become a distant memory in yet another scenario involving sex, money and murder.

  • 2


    Pops from the Barbershop

    "It's my nigga, Pop, from the barbershop/Told me he was in the gambling spot and heard the intricate plot/Of niggas wanna stick me like flypaper, neighbor/Slow down love, please chill, drop the caper"

    The Notorious B.I.G. gets an urgent page during the wee hours from Pops, a patron at a local barbershop who's come across information of him being set up to be robbed by a crew out of Brownsville aiming jack him for his riches. Pop breaks down the scenario swiftly before offering to help his comrade seek vengeance on his conspirators, but Biggie ultimately decides to handle his business on his own accord.

  • 1

    "Niggas Bleed"

    Arizona Ron

    "Since it's on, I call my nigga Arizona Ron/From Tucson, push the black Yukon/Usually had the slow grooves on, mostly rock the Isley/Stupid as a youngin, chose not the moves wisely"

    In the midst of planning a high-stakes robbery, The Notorious B.I.G., in character as Frank White, phones in his old cronie Arizona Ron, a hardened criminal with a hot streak and a thirst for murder and mayhem. After giving a brief rundown of his backstory, which includes appearances on America's Most Wanted and dodging a murder charge, the Notorious and Arizona Ron proceed to pull off the juxe, walking away with nearly $1.5 million in cash in a hail of gunfire.