1. Entertainment
Send to a Friend via Email

Your suggestion is on its way!

An email with a link to:


was emailed to:

Thanks for sharing About.com with others!

You can opt-out at any time. Please refer to our privacy policy for contact information.

11 Most Embarrassing Moments in Hip-Hop History


Rappers, like everyone else, have some dark, embarrassing secrets that they hope would remain just that - secrets. The difference between us and them is that public figures don't have the privilege of being able to deal with embarrassing moments in private like the rest of us. But Ross isn't the only rapper who's had to lick his wounds in public. Here's a rundown of 11 most embarrassing exposures in hip-hop history.

11. Dr. Dre in Pumps and Mascara

Dr. Dre
Photo © Michael Buckner/Getty Images

At the height of the Eazy-E vs Dr. Dre beef in 1992, the feuding friends traded insults non-stop. Just when it appeared as if Dre had sealed the deal with "Dre's Day," Eazy-E rebounded with "Real Muthaf-ckin' Gs." Eazy-E attacked Dre and Snoop, dubbing them studio gangsters who had never really witnessed the harsh realities of the "hood," but that wasn't the highlight. He devoted plenty of airtime to Dre's past as a member of the electro-pop group World Class Wrecking Cru' saying that he dressed in drag outfit while in the group. "Damn it’s a trip how a n-gga 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.

10. Akon or Con Man?

Akon always touted his past reputation as the ring leader of a notorious car theft clique. He claims to have been locked up for 31/2 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 would later revealed some inconsistencies between his account and the real deal. Sure, Akon was arrested several times, but the man who titled his sophomore LP Konvicted has never served jail time.

9. Eve's Dirty Secret

Ma$e once ran into Eve at a strip club years before she became famous, but he never mentioned it to anyone. Some internet jerk who stumbled upon pictures of Eve from her stripping days, however, wasn't so nice. In 2003, just as Eve was in the middle of revamping her image as an artist and aspiring 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 female. She later denied being a lesbian, saying 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 the stripper saga.

8. Eminem's N-Bomb Fiasco

© Interscope

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 nigger shit/I'm just here to make a bigger hit."

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

7. Young Buck's Emotional Breakdown

© Bryan Bedder/Getty Images

Before he was unceremoniously dismissed from 50 Cent's G-Unit crew, Young Buck spent plenty of time airing the group's dirty laundry. In various interviews, the Tennessee rapper claimed 50 owed him some royalties and that he was getting screwed in his deal. To stir up buzz for G-Unit's T.O.S. album, 50 unleashed an old phone conversation with Buck to the web. Throughout the call, Young Buck mentioned that he owes 50 some money while telling his boss about his own financial plight. At some point, he broke down over his dismissal from the Unit, "Sh*t got me confused, man," he said repeatedly. To which 50 Cent coyly replied, "You'll be alright, don't worry about it."

6. The Source's Fall from Glory

Eminem Source Cover

When pioneering hip-hop magazine The Source went bankrupt, the last explanation its Board of Directors expected to hear was, "Um...sorry, Dave and I 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."

5. Vanilla Lies, Lies, Baby

© Rob Van Winkle/Getty Images
For a while in 1990 or thereabout, everyone on the planet was combing through Vanilla Ice's past to see they could find any discrepancies in his stories. Ice repeatedly told the media that he had been raised in the mean streets of Miami. Adding salt to injury, Ice gave 3 different accounts of an incident, in which he claimed he was stabbed 5 times and lost half of his blood. It was later discovered that the tough-talking Ice wasn't raised in the streets. Robert van Winkle actually spent the better part of his teen life in an affluent Dallas suburb. His stories about attending an all-black Florida high school and living a rugged life of crime were revealed to be tall tales

4. Solange Goes Kung Fu on Jay Z

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 internvenes. A week later, the familiy made nice and released a statement saying that "families have problems and we're no different."  Truth.

3. Officer Rick Ross' C.O. Photos

© Henry Adaso/About.com

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 cuff 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. Pile of documents from the Florida State Department of Corrections later showed that Rick Ross had, in fact, worked as a Corrections Officer, forcing the Miami rap star 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."

2. Nas and Jay Had Something in "Carmen"

Many theories exist on why Jay-Z and Nas found themselves embroiled in one of the most dramatic feuds in hip-hop history. Was Nas envious of Jay's commercial exploits? Was Jay dissing Nas' girlfriend on "Is That Your Chick"? Nas' ex-girl Carmen Bryan claims she's the unintentional brain behind the beef. Both MCs initially tried to conceal the fact that Carmen, who has a daughter with Nas, had anything to do with the feud. In her memoir, Bryan reveals intimate details of her romp with Jay-Z and how it impacted the beef. In the same vein, Jay-Z admitted to the affair on the scathing "Super Ugly" freestyle. Disgusted by her son's rhymes, Gloria Carter demanded that Jay apologize publicly to Nas and his family. He obliged.

1. Cam'ron's No Snitching Campaign

© Asylum Records
During a 2007 appearance on 60 Minutes to discuss the role of snitching in urban communities, Anderson Cooper asked Cam'ron what he'd do if he knew a murderer lived next door. Cam's response defied reasoning and 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 and he would never condone it. After a Smoking Gun article unearthed document proving Cam's cooperation with authorities in 1997, he quickly found himself singing from a different hymn book. Cam apologized for his earlier statement.
  1. About.com
  2. Entertainment
  3. Rap/Hip-Hop
  4. Hip-Hop History
  5. Articles
  6. 11 Most Embarrassing Moments in Hip-Hop History

©2014 About.com. All rights reserved.