The 12 Most Embarrassing Moments in Hip-Hop History

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The 12 Most Embarrassing Moments in Hip-Hop History

Jay Z and Beyonce
(Photo by Neilson Barnard/Getty Images)

A few years back, tough-guy rapper Rick Ross was found to be a former correctional officer. Now, there's nothing wrong with being a CO. Well, unless you happen to be a rapper who built his career on tales about moving weight in the hood. Rick Ross denied it at first, but later copped to his old profession.

Ross isn't the only rapper who's had to lick his wounds in public. Rappers, big and small, have had a few embarrassing moments they hope would remain hidden. Unfortunately for them, they rarely have the privilege of being able to deal with embarrassing moments in private like the rest of us.

Here's a rundown of the 12 most embarrassing hip-hop moments.

02
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Eve's Dirty Secret

Pastor Ma$e once ran into Eve at a strip club, years before she became famous. Ma$ never mentioned it to anyone. Years later, some internet jerk unearthed pictures of Eve from her stripping days. In 2003, just as Eve was in the middle of revamping her image as an artist/actress, unflattering pics of her in full-on stripper outfit surfaced on the web to the amusement of many. Some of the photos showed the Ruff Ryders' first lady in a compromising position with another dancer. She later claimed that the other lady had been Photoshopped onto the original picture. Well, there was nothing doctored about the sex tape that turned up a couple years after, co-starring former Bad Boy producer Stevie J.

03
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Dr. Dre in Pumps and Mascara

CIRCA 1990: Photo of Dr. Dre
Raymond Boyd/ Michael Ochs Archives/ Getty Images

At the height of the Eazy-E vs Dr. Dre beef in 1992, the feuding friends traded insults non-stop. Just when you thought Dre had won the battle with "Dre's Day," Eazy-E bounced back with "Real Muthaf--kin' Gs." Eazy attacked Dre and Snoop, calling them studio gangsters who had never really witnessed the harsh realities of the hood, but that wasn't the highlight of the diss. He devoted plenty of airtime to Dre's past as a member of the electro-pop group World Class Wrecking Cru'. "Damn it’s a trip how a n---a can go so quick from wearing lipstick to smoking on chronic at picnics," he rapped. Eazy also threw in a promo pic of Dre from 1986 dressed in pumps and mascara to boot.

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The Rap Bible's Fall from Grace

Eminem Source Cover
Eminem Source Cover.

When pioneering hip-hop magazine The Source went bankrupt, the last thing the Board of Directors expected to hear was, "Um...sorry, Ray spent all the money on weed and bling bling." Like a 7-headed dragon, their problems multiplied and attacked from various angles.

A Manhattan lithographer sued for $30,000. A 5th Ave. jeweler petitioned for a $36,000 dent. The magazine's travel agent was owed $142,000. Former Editor-in-Chief Kim Osorio filed a sexual harassment lawsuit. Osorio's description of The Source work environment sounded like something straight out of a movie: a "raunched-out workplace where executives watched porn, smoked pot and called female employees b*tches."

05
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Diddy's UCLA Altercation

Diddy.jpg
(Photo © Gareth Cattermole / Getty)

On June 22nd, 2015, just a day after Father’s Day, Diddy embarrassed himself at his son’s training facility. Diddy was arrested after allegedly confronting a UCLA assistant coach. Diddy, whose son Justin Combs plays defensive back for the Bruins, was possibly upset at his son's lack of playing time.

Diddy was arrested on three counts of assault with a deadly weapon, the deadly weapon being a kettlebell. (Wait, Diddy can lift a kettlebell?) He was also charged with one count of making terrorist threats and one count of battery.

06
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Akon's Squeaky Clean Past

Akon always touted his past reputation as the ring leader of a notorious car theft clique. He claims to have been locked up for 3 1/2 years. He even rode his way to fame on the strength of a catchy single titled "Locked Up," in which 'Kon gave a supposedly autobiographical account of prison desolation. In fact, Akon was so obsessed with his felonious past that he named his label Konvict Music. That sound you hear at the beginning of every song he produces? That's the sound of a clanking cell door.

A Smoking Gun investigation later revealed some inconsistencies between Akon's story and official documents. Turns out that the man who titled his sophomore LP Konvicted has never served jail time.

07
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Eminem's N-Bomb Fiasco

Eminem during Eminem in Concert at the House of Blues - February 26, 2006
Kevin.Mazur/ Getty Images

In a desperate attempt to paint Eminem as a racist, The Source founders Benzino and Dave Mays emerged with a tape that caught a 17-year old Marshall Mathers using the N-word. On one of the songs from the 1988 tape, an amateurish Eminem spewed hateful venom at black women: "All the girls I like to bone have big butts/No they don't, 'cause I don't like that n****r shit/I'm just here to make a bigger hit."

Eminem explained that he wrote the song out of anger, having gone through a nasty break-up with his black girlfriend. He apologized and detailed the entire saga on "Yellow Brick Road," one of his best songs ever.

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Young Buck's Emotional Breakdown

Young Buck
Michael Loccisano/ FilmMagic/ Getty Images

No one will forget the time 50 Cent publicly gave Young Buck the boot. Before being unceremoniously dismissed from 50's G-Unit crew in 2008, Young Buck spent some time airing the group's dirty laundry. In a bid to build consensus among his fanbase, the Tennessee rapper claimed that 50 owed him unpaid royalties and that he was getting screwed in his deal.

Buck quickly forgot that 50 Cent is the King of Controversy. To build buzz for G-Unit's T.O.S. album, 50 unveiled an old phone conversation with Buck. Throughout the call, Young Buck admits that he owes 50 Cent a ton of money. He even goes on to tell his former boss about his own financial plight. At some point, he breaks down over his dismissal from the Unit, "Sh*t got me confused, man," he's heard saying repeatedly, amid choked up tears. To which 50 Cent coyly replied, "You'll be alright, don't worry about it." Of course, Buck had no idea he was being recorded. 50, you sneaky bastid.

09
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Jay Z's Elevator "Beatdown"

Jay Z and Beyonce
(Photo by Neilson Barnard/Getty Images)

In what may have been the longest elevator ride ever, Solange opened a can of whoop-ass on brother-in-law Jay Z. In the security camera footage leaked days later, Solange is seen yelling, kicking and spitting at Hov, while Beyonce watches. The karate chops continue until a bodyguard finally intervenes. A week later, the familiy made nice and released a statement saying that "families have problems and we're no different." Truth.

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Vanilla Lies, Lies, Baby

For a while in 1990 or thereabout, everyone on the planet was combing through Vanilla Ice's past to see they could find any skeletons in his closet. Ice planted doubts in the minds of his followers by repeatedly portraying an image of a tough guy. He told the media that he was raised in the mean streets of Miami. Worse, Ice gave three different accounts of an incident, in which he claimed he had been stabbed five times and lost half of his blood.

It was later discovered that the tough-talking Vanilla Ice was full of lies. The man born Robert van Winkle actually spent most of his teenage life in an affluent Dallas suburb. His stories about attending an all-black Florida high school and living a rugged life of crime were all found to be tall tales.

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Cam'ron's No Snitching Campaign

Cam'ron
Bennett Raglin/BET/Getty Images

During a 2007 appearance on 60 Minutes to discuss the role of snitching in urban communities, Anderson Cooper asked Cam'ron a simple question: What would you do if you knew that a serial killer lived next door? Cam's response defied reasoning. It ignored common sense:

"If I knew a serial killer was living next door to me? I wouldn't call and tell anybody on him. But I'd probably move. I'm not going to call and be like, 'The serial killer's in 4E.'"

Cam went on to say that snitching was in strict violation of his code of ethics--that he would never condone it. After a Smoking Gun article showed documents proving that Cam had actually violated his own code in the past. Police reports showed Cam cooperated with authorities during a criminal investigation in 1997. The Harlem rapper quickly found himself singing from a different hymn book. To his credit, Cam apologized for the earlier statement.

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Officer Rick Ross' C.O. Photos

Apparently the party favors were heavy in rotation. Rozey, Tunechi and Khaled Hustle Hard onstage at the BET Awards. &copy Kevin Winter/Getty Images

Rick Ross modeled his rap persona after the infamous drug kingpin Freeway Rick Ross. In reality, Ross' past most resembles that of the men who handcuff drug dealers than a kingpin.

When photos of a young Rick Ross in prison guard uniform turned up on the web, he consistently denied the reports. Ross insisted that it was a doctored image aimed at assassinating his character. Piles of documents from the Florida State Department of Corrections later showed that Rick Ross had, in fact, worked as a Corrections Officer, forcing the MMG boss to finally admit to his noble past. "In the game we in, it's real competitive," Ross later explained. "Competitors have to do what they have to do to eat."

13
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Nas and Jay Z's Dirty Laundry

Jay z Nas
Getty

There are many theories on why Jay Z and Nas found themselves embroiled in one of the greatest battles in hip-hop history. Was Nas jealous of Jay's commercial success? Was Jay dissing Nas' girlfriend on "Is That Your Chick"? Was this really about the imaginary throne of hip-hop? Nas' ex-girlfriend Carmen Bryan may escalated the feud. Both MCs initially tried to conceal the fact that Carmen, who has a daughter with Nas, had anything to do with the beef. In her memoir, however, Bryan shares intimate details of her romp with Jay Z and how it impacted the battle between Nas and Jay. In the same vein, Jay Z admitted to the affair on the scathing "Super Ugly" freestyle. Disgusted by her son's rhymes, Gloria Carter asked Jay apologize publicly to Nas and his family. Jay obliged and apologized to Nas and his family. Nas and Jay would eventually put the feud behind them. Hey, they're even besties on the mic now.

See Also: Jay Z vs Nas: The Story Behind the Feud | Top 10 Hip-Hop Beefs20 Awkwardly Hilarious Rap Album Covers | The Worst Rap Albums by Great Rappers | 10 Rappers Who Actually Killed People

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Adaso, Henry. "The 12 Most Embarrassing Moments in Hip-Hop History." ThoughtCo, Mar. 3, 2017, thoughtco.com/most-embarrassing-moments-in-hip-hop-history-2857994. Adaso, Henry. (2017, March 3). The 12 Most Embarrassing Moments in Hip-Hop History. Retrieved from https://www.thoughtco.com/most-embarrassing-moments-in-hip-hop-history-2857994 Adaso, Henry. "The 12 Most Embarrassing Moments in Hip-Hop History." ThoughtCo. https://www.thoughtco.com/most-embarrassing-moments-in-hip-hop-history-2857994 (accessed November 19, 2017).