Charles Hamilton’s Greatest Fails: A Retrospective

Around this time last year Charles Hamilton was a relatively unknown Harlem MC that became one of the most talked about upcoming hip-hop acts in a matter of weeks. Blogs were showing love and early mixtapes signaled promise. Hell, the first time we saw this guy spit was in a cipher with Kanye West and The Game. Not a bad first impression. But what a difference a year makes.

It’s not like we think the Sonic-obsessed rapper’s music has gotten wack (it’s still pretty consistently dope), but even his diehard fans would be hard-pressed to overlook this guy’s bizarre career missteps over the past 12 months. The latest Charles Hamilton controversy surrounds his decision to list the late James Yancey, better known as J. Dilla, as the executive producer of his debut album, This Perfect Life. The explanation? What he describes as a “paranormal relationship” with Dilla. Huh?

We give the kid some credit for keeping his name in the news in an era where fans are more fickle than ever, but unfortunately it’s become less about his music, and more about his public failures. Some of these are just normal growing pains of a new artist, but a lot of them could’ve been avoided if Charles would just take a take deep breath and log off every once in awhile. With that said, here’s a full breakdown of Charles Hamilton’s greatest fails as rated by our Rick Ross Fail Scale. Sorry Sonic…

SOULJA BOY TOLD ‘EM
WHEN: December 2008
• Charles Hamilton blamed Soulja Boy for hipster-rap’s lack of mainstream acceptance in an interview and obviously forgot to check the kid’s online-beef track record. Soulja Boy fired back with one of his infamous video responses and laid into Charles for over seven minutes. Ether moment: “X out the Sonic. You might wanna fuck with Mario. You might wanna eat a mushroom. Wooka wooka wooka.” Then after conspiracy theories about the authenticity of the beef developed (both are Interscope artists), most blogs, including Nah Right, never even posted Charles’ Auto-Tuned response. Fail.

Rick Ross Fail Scale:

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CAN’T TAKE YOU SERIUS
WHEN: January 2009
• Charles Hamilton handled old heads Rhymefest and Uncle Luke just fine, but he finally met his match when veteran battle rapper Serius Jones stepped up. “Your clothes look like the inside of a pussy.” Ouch. It was a good battle though, and while hip-hop may have won, Charles Hamilton definitely lost. In all fairness: we know your pea coat didn’t cost $2,000, Serius.

Rick Ross Fail Scale:

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JACKIN’ FOR BEATS
WHEN: March 2009
• Underground producer Black Spade cried foul after noticing Charles Hamilton’s self-produced song “Shinin’” bears a striking resemblance to one of his beats (compare the tracks here). Of course, Charles denied the accusation and even posted his Pro Tools session file online in an attempt to clear his name. Unfortunately for him, the file turned out to be self-incriminating and pretty much confirmed—as evidenced above—that he did jack Black Spade’s beat. Um, fail.

Rick Ross Fail Scale:

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SONIC DOESN’T LOVE COLLEGE
WHEN: March 2009
• Oh, how nice of Charles Hamilton to freestyle with college kids after a concert. It just sucks when your fans can outshine you. Sure, Charles didn’t appear to be battling as hard as the fan was, but you should never half-ass it when cameras are rolling. The guy with the deal and the Interscope machine behind him should never let anyone think that he lost a battle to this kid. Not even for a second.

Rick Ross Fail Scale:

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CHARLES HAMILTON IS A DIRTY KID
WHEN: April 2009
• On meeting Pharrell in an interview with Nylon Guys: “[We met at] the Four Seasons, right?” says Hamilton. “I had just taken a shower that day for the first time in a couple of days.” Need we say more?

Rick Ross Fail Scale:

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WALE AND CHARLES FIGURE OUT WHAT’S BEEF
WHEN: April 2009
• Charles Hamilton and Wale have had a rocky relationship since people began grouping them together in the same “freshman class” collective. Charles denied firing shots early on, but by spring, a real feud developed. The labelmates tried to cover their tracks and called the beef “fake” on Twitter, but that didn’t last long. Wale’s hilarious jab from the clip above combined with his comments in our recent interview might not have signaled a full-on assault, but they were pretty funny. Chalk it up to a W for the D.C. guy.

Rick Ross Fail Scale:

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CORY GUNZ GOES OFF
WHEN: April 2009
• Cory Gunz and his Square Off cronies dissed Charles Hamilton on PMS Radio (no, really) because apparently, Sonic had been talking greasy. But that guy’s career is a mess too, so no L for Charles here.

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THE PUNCH HEARD ‘ROUND THE BLOGOSPHERE
WHEN: May 2009
• We give Charles Hamilton credit for not going the Chris Brown route and retaliating, but that doesn’t exempt him from scrutiny. Think about the last time you got punched in the face by a girl. Anything cool about that? Didn’t think so. Unfortunately for Charles, Briana Latrise’s right hook became entertainment for millions and spawned even more jokes. The Pink Panther doll attached to his arm significantly increased the fail factor too. Sonic definitely lost his rings with this one. And those corny couples therapy sessions after the fact? Not a good look.

Rick Ross Fail Scale:

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CHARLES HAMILTON IMAGINES WORKING WITH DILLA
WHEN: June 2009
• Earlier this week, Charles Hamilton posted cover art for his debut album, This Perfect Life, on his blog. Aside from the failure that is being signed to a major and having your glorified mixtape “debut” released for free online, Charles caused an uproar by crediting the deceased legend, J. Dilla, as the executive producer of the album. Charles said that proceeds (from a free album?) will go to the J. Dilla Foundation, which apparently doesn’t exist. Ma Dukes doesn’t even know who the kid is. Now he’s saying that he worked with Dilla through a “strictly paranormal relationship.” FOH.

Rick Ross Fail Scale:

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RIHANNA OBSESSION GOES NOWHERE
WHEN: 2008 – Present
• We all love Rihanna in one way or another, but when you blog about her regularly and fabricate an imaginary relationship with her (“Cuz word on the street is I only hear boo when Rihanna’s referring to me.”) while another young rapper is rumored to be getting it in with her, you lose. That loser in this situation would be Charles Hamilton. May the fail be with you.

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