Can’t say they’re gangsta with a straight face.
DJ Khaled
I watched about six minutes of this DJ Khaled on MTV Cribs before I decided on the topic for this article. Listening to this man talk was just straight up bad. From yelling “We da bessssst,” upon entry into his home (and repeating it countless times after that), to basically overdoing every physical and verbal aspect of the stereotypical gangster rapper, there’s maybe an extremely small chance that DJ Khaled is as gangster as he makes himself out to be. Since he completely blew that image out of proportion on Cribs, though, that’s highly unlikely. Mr. Khaled Khaled is by far the most annoying rapper I have ever had the misfortune of noticing.
Kevin Federline
Why oh why didn’t you just stick to dancing, K-Fed? Oh right, you wouldn’t have gotten half of Britney Spears’ fortune if you did. Kevin Federline started out as a backup dancer, then went into modeling, rapping, and being Britney’s baby daddy. His rap “career” was just a huge embarrassment to hip-hop, with his debut album being dissed by everyone in every direction; you can’t really rap about how you’re “gangster” and a “star” while every song on your album is about how you’re going to throw away your (insanely wealthy) wife’s money on weed and parties. It doesn’t work, Fed-Ex.
Akon
Like 50 Cent, Akon has built his entire image on the “hardened gangster.” Unlike 50 Cent though, Akon’s street cred is completely hollow. For a guy who brags in every other interview about being an ex-ringleader of a huge car theft ring, writes songs about being “Locked Up,” and has a record label called “Konvict Muzik,” Akon has never been convicted of anything substantial. Ever. Actually, he did do three years probation for gun possession, but really? Gun possession? Aren’t guns more common than fast food in the States?
Rick Ross
No, this ain’t Ricky Ross the LA drug trafficker; this is William Leonard Roberts II. The big thing with this big man is this: he’s no drug dealer; he used to be a corrections officer. Yeah, he had a gun alright. Thing is, he wore the badge too. Rick Ross also claimed to have gang ties to Miami’s Carol City Cartel when he was busted for marijuana in ’08. Unfortunately, he couldn’t prove it, his lawyer prove it, and the officer in charge had to take his case off the gang task force. Paper gangster much?
50 Cent
Okay, okay. I get that Fiddy has the roughest childhood out of all five rappers/singers on this list. No father, mother was murdered when he was eight, grew up in Queens, sold crack, and even got caught at his high school with drugs and guns – G-Unit isn’t an empty name. However, as of right now, I think it’s safe to say that 50 Cent doesn’t have much time for anything other than straight business. He has a young son who’s a pretty important part of his life, from what he’s said in interviews, and it’s hard to imagine him going back to the street life, especially now that he’s made his gold. Curtis Jackson III is in business with Reebok, Vitamin Water, movies, video-games, and TV – in addition to music, of course. You’re more likely to find him in a suit than swinging a rag, although if he is swinging one, it’s probably Louis Vuitton. He’s come a long way, and I have to say that out of the five artists on this list, he’s the most deserving of mine, so props to you, 50.