Popular Culture

15 Rappers Who Weren’t So Gangster When They Were Young



Let’s be honest: being young isn’t really that gangster. Breastfeeding, wearing diapers, soiling yourself, crying uncontrollably — come to think of it, this was pretty much an average day in the life of Ol’ Dirty Bastard. I take it back. Being young is totally gully. With that in mind, not every rapper was representing in their younger days. Should it surprise us that many rappers acquire their gangster posturing as a promotional tool to further their calculated careers? Naw, son. Should it delight us to revel in the juicy details of their hypocrisy? Hellz yeah!

Rick Ross

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Other rappers get Jesus bling. Rick Ross’ custom made medallion sports his own giant, scowling visage. It’s like twice the Rick Ross staring you down. That kind of intimidation factor can really help you in certain careers: rapper, nursing home manager, and corrections officer. Rick Ross has done two of those. Rick Ross, cocaine braggart, was a screw. 50 Cent spent a lot of time beefing with “Officer Ricky,” and making a lot of drama over the fact that Ross had worked the other side of the prison system. He also narrated a sex tape featuring the mother of one of Ross’ children (I refuse to say “baby mama,” it smells like the Social Services building). All this grotesque public bickering makes one long for the days when rappers settled their beef by hiring someone to shoot the other guy.

LL Cool J

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It’s a fact that Ladies Love Cool James. Ladies really love men who spent their youth singing in the church choir, boy scouting, and working as a paperboy. Ladies also like a man who is good with children, and LL was originally in the film “Rugrats Go Wild!” as the voice of a Piki doll, but his character was cut from the final version. Ladies love men who love and respect their mothers. When Mama says “Knock him out,” LL is the first one to respectfully obey her commands. Also, LL is a Republican, which chicks actually hate. Ladies really don’t want to hear about love of free markets and increased defense spending and limiting of their medical rights. Believe me, I’ve tried all these as pick up lines. You could try these at the Republican Convention and still strike out. Therefore, I stand corrected: Ladies Do Not Love Cool James. Un-gangster.

Marky Mark

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Marky Mark (I refuse to say “Mark Wahlberg,” it smells like Jeremy Piven’s bluetooth) built his hardcore rap career off the image of a tough, streetwise kid. He refused to follow in the footsteps of his older brother and join New Kids on the Block because of their squeaky clean image. Marky wasn’t going to go soft. Marky was hard. Hard enough to severely beat two middle aged Vietnamese men and shout racial slurs during his arrest. Beating confused strangers because of their race is not gangster. He should have been beating confused strangers because of their mistakenly inferred gang affiliation (some of just look good in blue paisley, don’t hate). Marky would probably like all of us to forget his rap career, and especially forget his hate crimes against immigrants (that’s Neil Diamond’s game, Marky!), but all I can think of whenever I see Marky Mark in a movie is him delivering a vicious race-beating while humming “Good Vibrations.” That’s probably why I didn’t care for “The Happening.” Just kidding, Marky Mark race-beatings would have vastly improved “The Happening.”

Young Jeezy

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Young Jeezy dropped a song called “Mr. 17.5.” According to him, that’s the going rate for a kilo of coke. I wouldn’t know, since the only coke I get comes in a can. This dude named Emilio who hangs around outside the Sunoco is paranoid, so he slips all his yay in empty cans, throws it down and walks away and then I can go pick it up after he’s left. It’s a pretty smart system actually. What were we talking about? Oh right, so fellow rapper Pimp C called Jeezy out on the price, claiming he scores keys at 10k, and 17.5 is pure fiction. Both have deflected from the comments since; Young Jeezy claims Pimp C’s comments were not about him (did someone else write a song called “Mr. 17.5?”) while Pimp C has claimed he has nothing against Young Jeezy. All this backtracking and apologizing really makes one long for the days when rappers settled their beef by paying off expendable gang members to kill their rivals in drive by shootings. That was classy.

Robert Van Winkle

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Robert Van Winkle, or Vanilla Ice, has taken his fair share of abuse for not being authentically from the street. It makes it difficult to claim street cred when your father sells reasonably priced used cars. It’s not really Van Winkle’s fault he wasn’t born into poverty. And who’s to say the middle class can’t rap too! (“This William Safire editorial be ignoring issues of class/ whack muthawriter lying worse than Jason Glass.”) Sorry, the middle class is not allowed to rap. Mr. Van Winkle must have realized this early on because the lyrics to “Ice, Ice Baby” recount an attempted car jacking: “Gunshots rang out like a bell/ I grabbed my nine all I heard were shells/ Falling on the concrete real fast/ Jumped in my car slammed on the gas.” “Ice, Ice Baby” has become such a kitschy cultural relic that I forgot it recounted a car jacking. It also does it very poorly. Why would the narrator only hear shells during a presumably loud gun battle and if that’s the case doesn’t it conflict with his previous statement “gunshots ring out like a bell?” Also, the simile “like a bell” is a cliché. This is why the middle class should not rap and should not analyze rap. Let’s get out of here.

Busta Rhymes

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Back in the day, Busta was a part of a the hip-hop group Leaders of the New School. The moniker was decidedly un-gangster. Taking group pictures in front of a school bus to emphasize your un-gangster name is most un-gangster. The most un-gangster thing about Leaders of the New School is how they broke up. Young Busta was supposed to drive Leaders of the New School to a music festival, but unfortunately flaked out “to get dome” from a girl. Leaders of the New School, pioneering rap geniuses, broke up because Busta blew them off for girl and forgot to give them a ride (None of the other members own cars? Do they actually ride the school bus?). That sounds less like “Boyz n the Hood” drama and more like “Degrassi Junior High” drama. Thankfully, Busta has spent time making up for his wasted youth and association with education by more recently engaging in assault and drunk driving.

Young Buck

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Former G Unit member Young Buck peaked his gangster persona pretty quickly. Wikipedia says Buck started out as a “techno singer” rather than a rapper (what the hell is a “techno singer” by the way?). After Buck fell in with G Unit he fell out pretty quickly and started running into financial trouble, which is never very gangster. Eventually he called his former mentor, 50 Cent, and spent a great deal of time crying on the phone. Of course, 50 leaked the call to his website (50 Cent is like the rap world’s “Heathers,” right?) In any case, after crying on the phone like a teenage girl (what adult cries on the phone not during phone sex?) Young Buck pretty much strained any chance that his career could make a comeback. Supposedly he’s still in his contract with G Unit, but trying to get out of it and make his own label. It’s called Crying on the Phone Records.

Asher Roth

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Asher Roth wasn’t gangster when he was young, but to be fair he’s not really gangster now. His most solid joint is “I Love College.” Jesus. I guess that’s what growing up in a Philadelphia suburb does to you. After bragging about not having learned anything from classes Roth busts out “Yeah, of course I learned some rules/ Like don’t pass out with your shoes on/ And don’t leave the house ’til the booze gone/ And don’t have sex if she’s too gone/ When it comes to condoms put two on.” Ah yes, he learned the hallowed collegiate rule of “Don’t date rape your acquaintances,” and the ever useful “Practice methods of STD prevention in a manner that’s dangerously ineffective.” Steve Rifkind, current chairman and CEO of SRC Records (home to artists like Akon and Wu-Tang Clan), has said of Roth’s success: “The street is the street… but that’s changing. It’s also wherever the college street is, and, also, the street’s on the Internet now.”


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Common also went to college; he studied Business Administration at Florida A&M University. Unlike Roth, Common likes to promote the value of education in his career and openly encourages kids to go to college, a decidedly un-gangster stance to take.


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What can be said about a rapper who appears in photos with Lil Wayne while throwing up gang signs. Gangster. But, dear reader, what if his real name is Aubrey and he appeared on “Degrassi Junior High,” and (gasp!) he’s Canadian. Not so gangster. Please stop rapping about your ex-girlfriends, Aubrey.

Lil Wayne

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Lil Wayne was in the gifted program at Lafayette elementary in New Orleans, and also in a production of “The Wiz.” He also accidentally shot himself in the chest with a handgun when he was twelve.

He was also on the honor roll in High School. He also dropped out. Who am I kidding? It’s really hard to hate on Lil Wayne. Wayne’s gangster persona seems less like a put on than many other rappers. For one, he’s always getting arrested and unlike most celebrities, he ends up in jail. He has also been experimenting, for better or worse, with rock (the genre, though probably also the substance), so his ability to chameleon into different personas seems like an extension of his undeniable creativity. Let’s give Lil Wayne a pass here. Prolific creativity and trail blazing ingenuity wasn’t really gangster, but Lil Wayne made it gangster. That’s a welcome game changer. Also, I would pay so much money to see a Lil Wayne version of “The Wiz.”

Ice Cube

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Cube’s coming straight outta Compton, to study architectural drafting at Phoenix Institute of Technology. Ice Cube is another example of a “gangster” (and Cube might arguably have been the epitome of “gangster rap”) who didn’t start out or end up with that persona, but definitely dabbled. It used to be a good day if he didn’t even have to use his AK (do they actually let you bring an AK into Spanish 201? I didn’t see it on the syllabus…), now it’s a good day if “Are We There Yet” does well at the box office. Ice Cube’s considerable influence in the hip-hop world can’t be denied, even if his personal life and his rap persona don’t match all the time. First with N.W.A. and then as a solo artist, Cube made the political personal with his scathing critiques of inner-city poverty, police oppression, and systematic racism. Without Ice Cube the cultural milieu of the modern gangster wouldn’t exist, and Cube brings the most worthwhile political elements to the genre.

Kanye West

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Another famous college dropout, Kanye West spends a lot less time rapping about the mean streets of Chicago these days. On his first record though, he busted lines about having to “rap, sell crack, and get a job.” That seems to be less on his mind these days. As oppressive as he wanted to paint his gritty urban upbringing, his mother was an English professor and his father was an award winning photographer. The gangster persona never really suited West, and his brief flirtation with it on some tracks of “The College Dropout” is overshadowed by the realities of his ego. He readily admits on track after track that he’s a young man who’s too often seduced by style rather than substance, and has a hard time reconciling economic realities and out-of-reach dreams. At this point in his career, Kanye seems to have left most of his gangster persona behind (unless making teenage white girls cry is gangster), but a lot of the framework of the confused persona that skirts between excessive arrogance and  apologetic humility still remains. The fact that Kanye makes it enjoyable is actually proof of his immense artistic talent. Narcissists rarely take the time to pull you into their worldview, but Kanye does it with style.


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Before he dropped his major label debut “The Slim Shady LP”, Marshall Mathers dropped a decidedly different record with a decidedly different persona. “Infinite,” Em’s first record was pretty harshly critiqued in his hometown of Detroit. Em’s style was seen as derivative, and lyrics tended toward overly stylized and ultimately meaningless wordplay. When he does get near substantive ground, he raps about dreaming of a better life for himself and his family (as heard on the track “Never 2 Far”), which is decidedly un-gangster. Em himself has said that he was still searching for his style on “Infinite” and the record feels that way. When he discovered the trademark rage and intense flow that comprise much of his more familiar work, I’m sure he and everyone else in earshot were thankful.

Dr. Dre

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Let’s not make a rookie mistake: don’t forget about Dre. Though Dr. Dre grew up in Compton, went on to make beats for N.W.A., Snoop Dogg, Eminem, 50 Cent, The Game, and nearly every other major player in the hip-hop world, he started out with a group called World Class Wrecking Cru. The Cru was good at wearing plastic clothes, prop jewelry, posing, and generally being very, very un-gangster. As Dr. Dre grew older, thankfully his penchant for sweater shirts and wearing a stethoscope waned, and he helped pioneer gangster rap instead. As cultural critic Michel Foucault once said in one of his lectures on power and identity: “Damn it feels good to be a gangster.”


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