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)

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*

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.

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.

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.

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.

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.

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.

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.]

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.

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.

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.

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.

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

Signing to Death Row

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

Shan

Wayne kissing Baby

Wayne the rocker

Tony Yayo

Nas and Kelis

[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)