The 13 Worst Career Moves in Hip-Hop History

Written by Barbie Bardot. Posted in The Biz

Published on August 08, 2009 with 85 Comments">85 Comments

50 Rule/Ja Cent
Sometimes the only thing separating a Fif from a Ja is one smart move.

Pesky decisions swarm us daily in life, like a troop of blind killer bees. Most of us just swat them with the slipshod petulance of a dog’s tail. But our hip-hop heroes know better, because when it comes to running a career into the ground or digging a hole bigger than the U.S. deficit, no one knows better than rappers. Here are 13 hip-hop artists to meditate on next time you run into an occupational obstacle, for they are the ones who made modern rap’s worst career moves. (– Rizoh)

Alfamega
13. Alfamega’s D.E.A. saga
Alfamega’s quick rise and fall has been well documented. His career has been in a downward spiral ever since word leaked that he may have been a D.E.A. informant in the past, but he doesn’t seem to know when to stop talking. Last week Alfa released a track in which he was going at T.I. [Ed: Mega denied this, but who cares? The song is caca anyway. - Rizoh] Yeah, homie, that’s a good way to reignite your career — by taking digs at your boss while he’s in jail. *blank stare*

 

Yung Berg

12. Yung Berg’s “dark butts” comments
Poor Yung Berg. Dude could actually craft a nice little catchy song. However, he couldn’t manage to keep his mouth shut. 1st came his “dark butts” comment — he did an interview in which he said he prefers light-skinned girls over darker-skinned girls. Referring to darker-skinned girls as “dark butts,” though, wasn’t the best idea. Neither was the weak apology that came after he caught flack for it. Then he kept running off at the mouth and eventually got smacked up. After talking trash in Detroit, Berg got a few hits upside his head and his transformers chain snatched. Then Maino smacked him up. Lesson to be learned here? Sometimes, its just best not to talk sh-t, especially if you cant back it up.

 

mc_hammer

11. Hammer’s brief stint as a gangsta rapper
Whose bright idea was that? It was so unbelievable it ended up being more comical than anything. Remember the “Pumps And A Bump” video? Someone forgot to tell Hammer that gangstas don’t wear banana hammocks. Epic FAIL, indeed.

 

Lauryn Hill

10. Lauryn Hill‘s self-imposed music exile
Whether it was the good Marley being administered to her on a daily basis, or the pressure of the music industry, we’ll never know. Either way, L-Boogie ruined an amazing career by losing her mind after the multiple-Grammy winning Miseducation of Lauryn Hill was released. (Check her interviews and her MTV Unplugged CD that came after that, if you don’t remember). Please Lauryn, get better and come back. Hip-hop needs you.

 

buck-is-higher-than-a-kite
9. Young Buck crying on the phone to 50 Cent
It’s a damn shame what happened to Buck, really. For years he was on top of the charts as a G-Unit soldier. He dropped two impressive solo albums and had folks debating if he was the best lyricist in his crew and if he could carry the torch for them in their latter years. Then he started to buck against 50 Cent. Buck went on radio stations saying that Fif’s beefs weren’t his beefs, and it seemed that all wasn’t right between them, but everyone, including Buck, kinda hoped they’d eventually resolve their differences. Then, 50 dropped the equivalent of an atomic bomb when he released taped conversations between him and Buck with the Nashville rapper crying on the tape. Hysterically. And apologizing. Repeatedly. *shakes head* After that episode, Buck was dropped from G-Unit and he went into hiding for awhile, albeit understandably. As of late he’s been releasing songs over the internet but Buck may be the only person who doesn’t realize his career is over yet.

 

charles-hamilton-calling-out-to-j-dilla

8. Charles Hamilton naming J. Dilla the executive producer of his album
Recently, Charles Hamilton has been on rap’s radar not for his talent but because of his ability to turn folks off with his personal commentary. He had a huge buzz going no matter what folks thought about him and then he named the late J Dilla as the executive producer of his debut album. What Charles perceived as paying homage to J. Dilla, with whom he claims to have some type of a paranormal relationship, was perceived by others as disrespectful. We haven’t really heard much from Chuck since that fiasco.

 

ll-vs-canibus

7. Canibus trying to play LL Cool J’s game
How many times have you heard a rhyme and thought a rapper was covertly getting at another rapper? How easily words can be misunderstood. Canibus and LL were on the same song. LL thought something Canibus said was disrespectful. They spoke and cleared it up (or so Canibus thought), but LL kept his incendiary verse against Bis on the same song, thus sparking a huge feud between them. Diss tracks ensued, LL was declared the victor [Ed: I'd like the name and address of everyone who declared LL victorious in this battle, so I can physically fight them - Rizoh], while Canibus was allegedly blackballed by LL’s industry cronies.

 

shhhh-x-is-praying

6. DMX’s frequent visits to the big house
In 1998, DMX was one of the most lyrically gifted rappers out. Who could forget his verse on the Lox’s “Money, Power, Respect”? Its Dark & Hell Is Hot and Flesh Of My Flesh, Blood Of My Blood came out in the same year and were both certified platinum. In fact, X was the second rapper (behind 2Pac) to have two albums released in the same year debut at number one on Billboard’s Top 200 chart. Problem was, at that point DMX really succumbed to his addiction problems and continually stayed on the radar due to his incessant arrests. [Here's hoping D can finally overcome his demons, because if Mase came back, I'm gonna need for DMX too.]

 

Shyne
5. Shyne signing to Bad Boy
December 1999. Club NY. I’m sure it’s a moment that Shyne Po would love to go back to and alter the events of. Remember how huge Shyne’s buzz was? You couldn’t go anywhere without hearing “Bad Boys” on the radio back then. It was all good until Shyne was found guilty and sentenced to 10 years in prison for shooting a gun in Club NY. It still baffles the mind how Diddy escaped scot-free from that incident. Shyne will be released from prison on October 6th. Diddy better watch his back.

 

Guerilla Black
4. Guerilla Black’s attempt at a rap career
First, if you’re going to rep a city make sure it’s where you’re truly from. Guerilla Black had a nice buzz going on with his “Compton” single. But then he caught a lot of flack for claiming a city that he was rumored not to be from. It didn’t help that he sounded like a Biggie Smalls impostor. Now he’s just another rapper that folks vaguely remember.

 

roc-family

3. Dame Dash and Biggs pissing off Jay-Z
C’mon man, it was supposed to be Roc La Familia for life! Everyone knew that when the Roc broke up Jay-Z would be okay but Beans, Freeway, the Young Gunz, Memphis Bleek, Noreaga, M.O.P. and countless others were left floundering. Not to mention Dame Dash could no longer afford to pay his bills…or afford his wife.

 

bad-boy-4-life
2. Signing to Bad Boy after Biggie died
Remember G. Dep, Black Rob, Ness, Babs, Chopper, Da Band, Dream, Mark Curry, Danity Kane, DeAngelo, Redman or Kain? Know what happened to any of them? Yeah…that’s what I thought. Drug addictions, jail and sitting on the shelf. Yeah, signing to Bad Boy would do that to you.

 

50 Rule/Ja Cent

1. Ja Rule challenging 50 Cent to a battle
This right here is the definition of career ending. Before this battle, Ja Rule was on the top of the world — every song he put out was a hit. Then he started beefing with 50 and it all came to a standstill. The best part of the whole thing? Fif stole Ja’s sing-songy style, did it better than him and dominated the charts for years after that. Ja’s career and Murder Inc. haven’t been the same, nor have they achieved that type of success since then.

 

Honorable Mention
I was pretty sure we left off some other regrettable career moves, so we posed the question on Twitter. Check out some of the responses below:

Chingy/Mims
chingy-and-mims

Signing to Death Row
getting-suged

Ja vs 50 was the most popular response, so I had to include at least one of them
ja-vs-50

Shan
shan-symphony

Wayne kissing Baby
wayne-kissing-baby

Wayne the rocker
wayne-the-rock-artist

Tony Yayo
yayo-the-grocer

Nas and Kelis
nelis

 

[Many thanks to Lyriciss for helping to jog my memory about some of these events (and the ensuing laughter that came with that conversation) ~ check him out on Twitter and Myspace] (–Black Barbie)

TRU

Barbie Bardot

Barbie Bardot is a writer of, and lover of, hip hop music & its culture, fashion, food and football. She currently resides in Brooklyn, NY, where for fun, she routinely walks in front of annoying tourists pictures, becoming the brown blur they can never identify. She runs www.itsbarbiebitch.com and is currently plotting ways to take over the world, a la Pinky and the Brain.

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  • kevvie kev

    Man I have to agree completely with Can-I-Bus crushing LL. I never understood the hype of LL ‘winning’ that battle. As Jeff said the people who declared him the winner were the people listening to him on the radio. Sucks that LL spoiled someone who was one of the rawest emcees at the time. The dude could have kept hip hop what it was in the early 90′s….and instead helped imo contribute to hip hop dying and radio rap becoming king.

    Hip hop is not dead, it’s just hiding.

  • matrix29

    Nobody with a job or brain cares about any “Rap Musician”. It is just a bunch of noisy whining and noisy undeserved bragging about how stupid they are. Good riddance to self-devalued rubbish.

  • matrix29

    Nobody with a job or brain cares about any “Rap Musician”. It is just a bunch of noisy whining and noisy undeserved bragging about how stupid they are. Good riddance to self-devalued rubbish.

  • matrix29

    Nobody with a job or brain cares about any “Rap Musician”. It is just a bunch of noisy whining and noisy undeserved bragging about how stupid they are. Good riddance to self-devalued rubbish.

  • MCSamurai

    @ matrix29

    go to youtube, or pandora and type in either Da Grassroots, Cunninlynguists, Jurassic 5 or Masta Ace and see if that doesn’t change your mind. like someone said before “hip-hop isnt dead its hiding” somewhere along the line in my early teenage years i turned off the radio and MTV and found other mediums and sources to find amazing hip hop music. you wont regret it.
    Happy Hunting

    One love, One life.
    Samurai aka “Deuce”

  • MCSamurai

    @ matrix29

    go to youtube, or pandora and type in either Da Grassroots, Cunninlynguists, Jurassic 5 or Masta Ace and see if that doesn’t change your mind. like someone said before “hip-hop isnt dead its hiding” somewhere along the line in my early teenage years i turned off the radio and MTV and found other mediums and sources to find amazing hip hop music. you wont regret it.
    Happy Hunting

    One love, One life.
    Samurai aka “Deuce”

  • MCSamurai

    @ matrix29

    go to youtube, or pandora and type in either Da Grassroots, Cunninlynguists, Jurassic 5 or Masta Ace and see if that doesn’t change your mind. like someone said before “hip-hop isnt dead its hiding” somewhere along the line in my early teenage years i turned off the radio and MTV and found other mediums and sources to find amazing hip hop music. you wont regret it.
    Happy Hunting

    One love, One life.
    Samurai aka “Deuce”

  • MrBrown

    #1 Failure is claiming to be from St. Louis. That city is a wasteland of talent. Nelly, Chingy, J-Kwon.. nothing good come outta that city in terms of Rap. It should be banned from making records

  • MrBrown

    #1 Failure is claiming to be from St. Louis. That city is a wasteland of talent. Nelly, Chingy, J-Kwon.. nothing good come outta that city in terms of Rap. It should be banned from making records

  • MrBrown

    #1 Failure is claiming to be from St. Louis. That city is a wasteland of talent. Nelly, Chingy, J-Kwon.. nothing good come outta that city in terms of Rap. It should be banned from making records

  • J to the AAP

    Canibus’ failure wasn’t in dissing LL (2nd Round Knock Out completely lived up to it’s title) but in releasing a lackluster debut album that wasn’t able to ride on the buzz that beef gave him.

    Still, good list! HipHop lost one with Lauryn’s hermit swagger.

  • J to the AAP

    Canibus’ failure wasn’t in dissing LL (2nd Round Knock Out completely lived up to it’s title) but in releasing a lackluster debut album that wasn’t able to ride on the buzz that beef gave him.

    Still, good list! HipHop lost one with Lauryn’s hermit swagger.

  • J to the AAP

    Canibus’ failure wasn’t in dissing LL (2nd Round Knock Out completely lived up to it’s title) but in releasing a lackluster debut album that wasn’t able to ride on the buzz that beef gave him.

    Still, good list! HipHop lost one with Lauryn’s hermit swagger.

  • Soldier Road

    Don’t really agree with the Lauryn Hill piece. Her Unplugged cd has some of the most intelligently written, honest, truthful lyrics this generation is likely to have the opportunity to listen to. That cd made her a genius in my book!

  • Soldier Road

    Don’t really agree with the Lauryn Hill piece. Her Unplugged cd has some of the most intelligently written, honest, truthful lyrics this generation is likely to have the opportunity to listen to. That cd made her a genius in my book!

  • Lo-Key the Architect

    I agree with Soldier Road about Lauryn. I never saw that clown thing and I won’t let that take away from her genius. She even said it in her unplugged album: if people “think” you’re crazy, then they leave you alone. She just wants peace and she got it.

  • Lo-Key the Architect

    I agree with Soldier Road about Lauryn. I never saw that clown thing and I won’t let that take away from her genius. She even said it in her unplugged album: if people “think” you’re crazy, then they leave you alone. She just wants peace and she got it.

  • KLK

    LL COOL J DIDN’T WIN THE MUSIC BATTLE, THE MEDIA MADE HIM THE WINNER BUT HE DIDN’T WIN!

  • KLK

    LL COOL J DIDN’T WIN THE MUSIC BATTLE, THE MEDIA MADE HIM THE WINNER BUT HE DIDN’T WIN!

  • JohnBlack

    Excellent post, but you mist a few:
    - Proof Bringing a gun to a club and threatening a bouncer wasn’t the smartest thing to do.

    - C-Murder bringing a gun to a nightclub. Also not very smart.

    I thought the goons were supposed to carry the guns?

  • JohnBlack

    Excellent post, but you mist a few:
    - Proof Bringing a gun to a club and threatening a bouncer wasn’t the smartest thing to do.

    - C-Murder bringing a gun to a nightclub. Also not very smart.

    I thought the goons were supposed to carry the guns?

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  • LORDKASEEM

    Peace…Niggaz know Canibus killed LL…”…make ya moms get on the phone..call Minster Farrakhan to ask him to squash it…I’m like NAAAAAAa he forgot what a real hip hop artist is…”
    They black balled Canibus on some Gay shit.

  • LORDKASEEM

    Peace…Niggaz know Canibus killed LL…”…make ya moms get on the phone..call Minster Farrakhan to ask him to squash it…I’m like NAAAAAAa he forgot what a real hip hop artist is…”
    They black balled Canibus on some Gay shit.

  • L.O.V.E,

    SIGNING to DTP…aka the write-off section on Luda’s W2′s

  • L.O.V.E,

    SIGNING to DTP…aka the write-off section on Luda’s W2′s

  • miguelito

    I hate when people say cannibus killed LL. I want everyone who says that to name your ten favorite LL and your ten favorite cannibus songs. How many cannibus songs are on your ipod? How many cannibus albums do you own? What was cannibus’s follow-up to LL’s response? LL did not need to be better he just needed to respond. Anybody over thirty knows LL has lyrics and although he did not bring his a-game we forgave him because a suspect rookie rapper does not deserve your a-game. Its like the high schooler dunking on lebron. Where is he now?

  • miguelito

    I hate when people say cannibus killed LL. I want everyone who says that to name your ten favorite LL and your ten favorite cannibus songs. How many cannibus songs are on your ipod? How many cannibus albums do you own? What was cannibus’s follow-up to LL’s response? LL did not need to be better he just needed to respond. Anybody over thirty knows LL has lyrics and although he did not bring his a-game we forgave him because a suspect rookie rapper does not deserve your a-game. Its like the high schooler dunking on lebron. Where is he now?

  • Walter

    Sleeping with Kat Stacks, lol…

  • Ronuno4

    Right in the Heart of NYC back then Canibus was declared winner on hot 97 on battle of the beats.
    Voted on by the ppl of NY where these guys where based out of.
    Now I’m not saying this is why I believe Canibus won. He won in my mind because 2 nd round lyrically murdered LL subsequent 3 diss retaliation songs.
    That’s right you don’t remember he layed out 3 tracks that where rumored to be ghost written.

    He did get blackballed.
    You guys need to show Canibus some more respect, he continued to write and inspire rappers of all walks. Lyrical artists.

  • 1417sinestro

    Maybe I’m a bit old or missed a point in time but I’ve NEVER heard of DeAngelo Redman. I don’t think he made it to the UK!

  • http://pulse.yahoo.com/_NUYLYXEBPG6TREUISWQDDNI5QI Killa J

    double post

  • http://pulse.yahoo.com/_NUYLYXEBPG6TREUISWQDDNI5QI Killa J

    Yo yall musta forgot bout ole boy houston summers… dude flipped the fuck out and snatched his eyeball out the fuckin socket like the bitch did ole girl on kill bill.. he had a nice buzz going and errything 

  • http://www.americanrxhealth.com/south-beach-java-diet-coffee-review South Beach Java

    I think Shyne’s mistake was getting those grills. He looks so retarded.. 

  • http://pulse.yahoo.com/_MQ5X7E7L6QTJ5YDDAAJNNQBANA mac

    Others:
    Rozay – lying about his past (he should be done already)
    T-Pain – using autotune to ‘sing’
    So much of this list is on point though

    PS, Always going to be an LL fan, but ‘Bus gave it to him lyrically. 

  • http://pulse.yahoo.com/_MQ5X7E7L6QTJ5YDDAAJNNQBANA mac

    Others:
    Rozay – lying about his past (he should be done already)
    T-Pain – using autotune to ‘sing’
    So much of this list is on point though

    PS, Always going to be an LL fan, but ‘Bus gave it to him lyrically. 

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  • http://www.soundkits.webs.com sound packs

    Yea really what was the deal with guirilla black, i never heard too much from but every time i see him in the hood he seems to be really welll for himself

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