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10 Rappers Whose Music Was As Scandalous As Their Lives5

By Dan Berry

10 Infamous Rappers Whose Music Was As Scandalous As Their Lives

It’s a hard-knock life, so why not rap about it and become a millionaire. But then again—mo’ money, mo’ problems.

That’s certainly the case for the lead character in Rhyme Animal, a series following an up-and-coming rapper who’s also a cannibalistic serial killer. But cannibalism aside, it’s the music that matters when engaging in the rap game. But it’s hard out there for a pimp. Often, a rapper’s art is a rapper’s reality, and reality has a way of getting in the way. And as we all know, harsh realities have a way of spawning some serious scandal.

Here are ten infamous rappers whose music was as scandalous as their lives – making both sinfully compelling.

Ryhme Animal – The Jump Off Bum Rush – The Freak Show

1. Tupac Shakur

Born in Harlem on June 16, 1971 (that’s right, he was originally an East Coaster), Tupac Shakur began his music career as a roadie and backup dancer for the alternative hip hop group Digital Underground before launching a solo rap career that saw him sell over 75 million albums worldwide. In addition to his career as a top-selling rap artist, he was a promising actor and a social activist. Still, it was the music that made him a legend. Most of Tupac’s songs are about growing up amid violence and hardship in ghettos, racism, and other social problems. And then there were his songs centered around his conflicts with other rappers (most notably, Biggie Smalls, whose wife Tupac boasted about bedding). During the East Coast-West Coast hip hop rivalry of the 1990s tensions quickly escalated into a deadly blood-feud, claiming the lives of numerous people, Shakur included.

In November 1993, Shakur and others were charged with sexually assaulting a woman in a hotel room. According to the complaint, Shakur sodomized the woman and then encouraged his friends to sexually abuse her. On the night of November 30, 1994, the day before the verdict in his sexual abuse trial was to be announced, Shakur was shot five times and robbed by two armed men in army fatigues after entering the lobby of Quad Recording Studios in Manhattan. According to the doctors at Bellevue Hospital, where he was admitted immediately following the incident, Shakur had received five bullet wounds: twice in the head, twice in the groin and once through the arm and thigh. He checked out of the hospital, against doctor’s orders, three hours after surgery.

In the day that followed, Shakur entered the courthouse in a wheelchair and was found guilty of three counts of molestation, but innocent of six others, including sodomy. On February 6, 1995, he was sentenced to 1½ to 4½ years in prison on a sexual assault charge. After serving eleven months of his 1½ to 4½ year sentence, Shakur was released from the penitentiary due in large part to the help and influence of the infamous Suge Knight, CEO of Death Row Records. Less than a year after being paroled, in September 1996, Tupac was shot 4 times in Las Vegas. He was taken to the University Medical Center, where he died of respiratory failure and cardiac arrest.

Due largely to a perceived lack of progress by law enforcement in the investigation of Shakur’s murder, many independent investigations and theories emerged. Because of the tensions between Shakur and Biggie (who was murdered in March 1997), there was speculation from the outset about the possibility of Biggie’s involvement. Biggie, as well as his family, relatives, and associates, vehemently denied all such accusations. In 2002, the LA Times published a story by Pulitzer Prize-winning investigative reporter Chuck Philips, who claimed to have uncovered evidence implicating Biggie, in addition to Anderson and the Southside Crips, in the attack. Philips quoted unnamed gang-member sources who claimed Biggie had ties to the Crips, often hiring them for security during West Coast appearances, and that Biggie colluded with the Crips to murder Shakur. In 2008, after The Smoking Gun reported that the documents relied upon by Philips for his story were fraudulent, the LA Times printed an official front-page retraction of Philips’ story. Less than five months later, Philips accepted a buyout and left the LA Times.

2. The Notorious B.I.G.

Christopher George Latore Wallace—popularly known as Biggie Smalls, Big Poppa, Frank White, and by his primary stage name The Notorious B.I.G.—grew up in Brooklyn, NY, and by the age of 12 was already selling drugs. At 17, Wallace dropped out of high school and became further involved in crime. In 1989, he was arrested on weapons charges and sentenced to five years’ probation. In 1990, he was arrested on a violation of his probation. A year later, Wallace was arrested in North Carolina for dealing crack cocaine. He spent nine months behind bars until he made bail.

Wallace began rapping when he was a teenager and success seemed inevitable. He quickly gained increased exposure and notoriety, leading to his debut album, Ready to Die (released on September 13, 1994) that reached #13 on the Billboard 200 chart, eventually being certified four times Platinum. The album, released at a time when West Coast hip hop was prominent in the U.S. charts, according to Rolling Stone, “almost single-handedly… shifted the focus back to East Coast rap.”

In his year of success, Wallace became involved in a rivalry between the East and West Coast hip-hop scenes with another legendary rapper, Tupac Shakur, his former friend and associate. In an interview with Vibe magazine in April 1995, while serving time in Clinton Correctional Facility, Shakur accused Uptown Records’ founder Andre Harrell, Sean “P Diddy” Combs, and Wallace of having prior knowledge of a robbery that resulted in him being shot repeatedly and losing thousands of dollars worth of jewelry on the night of November 30, 1994. Though Wallace and his entourage were in the same Manhattan-based recording studio at the time of the occurrence, they denied the accusation.

When Shakur was shot multiple times in a drive-by shooting in Las Vegas, Nevada, on September 7, 1996, and died six days later of complications from the gunshot wounds, rumors of Wallace’s involvement with the murder were reported almost immediately; but Wallace denied the allegation claiming he was in a New York recording studio at the time.

On March 9, 1997, at around 12:30 a.m., Wallace and his entourage left an after party for the 11th Annual Soul Train Music Awards in two GMC Suburbans. When Wallace’s truck stopped at a red light, a black Chevrolet Impala pulled up alongside the truck. The driver of the Impala, an African American male dressed in a blue suit and bow tie, rolled down his window, drew a 9 mm blue-steel pistol and fired at the GMC Suburban – four bullets hit Wallace in the chest. Wallace’s entourage rushed him to Cedars-Sinai Medical Center, but he was pronounced dead at 1:15 a.m.

Wallace’s murder remains unsolved and there are many theories regarding the identities and motives of the murderers. In late 2010, the case was “reinvigorated” as a result of new information that is being investigated by a task force composed of the LAPD, the L.A. County District Attorney, and the FBI.

3. Eazy-E

In 1987, Eric Lynn Wright (known by his stage name Eazy-E) used the profits from his drug sales to co-found Ruthless Records with Jerry Heller. When Ruthless signees Dr. Dre and Ice Cube wrote the song “Boyz-n-the-Hood,” Eazy-E formed the groundbreaking hip hop group N.W.A. with Dr. Dre and Ice Cube. (DJ Yella, MC Ren, and Arabian Prince were later added.)

N.W.A began to split up after only a few years together after Jerry Heller became the band’s manager. Dr. Dre recalls, “The split came when Jerry Heller got involved. He played the divide and conquer game. He picked one nigga to take care of instead of taking care of everybody, and that was Eazy. And Eazy was like, ‘I’m taken care of, so fuck it.’” Dre sent Death Row Records CEO and strongman Suge Knight to look into Eazy’s financial situation because he was beginning to grow suspicious of Eazy and Heller. Dre asked Eazy to release him from the Ruthless Records contract, but Eazy refused. The impasse led to what reportedly transpired between Knight and Eazy at the recording studio where Niggaz4life was recorded. After he refused to release Dre, Knight declared that Eazy had kidnapped Heller and was holding him prisoner in a van. However, the rumor did not convince Eazy to release Dre, and Knight threatened Eazy’s family. Knight gave Eazy a piece of paper that read Eazy’s mother’s address, with Knight telling him “I know where your mama stays.” Eazy finally signed Dre’s release, officially ending N.W.A.

The feud with Dr. Dre continued after a track on Dre’s The Chronic contained lyrics that dissed Eazy-E. Eazy responded with the EP It’s On (Dr. Dre) 187um Killa, featuring the tracks “Real Muthaphuckkin G’s” and “It’s On.” The album, which was released on October 25, 1993, contains pictures of Dre when he was a member of the Electro-hop World Class Wreckin’ Cru, where Dre wore “lacy outfits and makeup.”

On February 24, 1995, Eazy-E was admitted into Cedars Sinai Medical Center in Los Angeles with what he believed to be asthma. Instead, he was diagnosed with AIDS. During the week of March 20, having already made amends with Dr. Dre and Snoop Dogg, Eazy-E drafted his last message to fans. One week after making that announcement, Eazy succumbed to the disease. He was 31 years old.

4. Ice-T

Ice-T is the original O.G. He is also likes to go against the grain. The rapper/actor/lover of preposterously proportioned white women actually got his start in the streets as a pimp. From lover to fighter, Ice-T went on to record the legendary song “Cop Killer” – the self-proclaimed 1992 “protest record” that provoked much controversy and negative reactions from political figures such as then-President George H.W. Bush, then-Vice President Dan Quayle and Tipper Gore, co-founder of the Parents Music Resource Center. But, a true entrepreneur at heart, he protected his career by recalling the album. He would go on to start feuds in the rap world with public arguments involving rappers Redman, Ice Cube, LL Cool J and DeAndre Cortez “Soulja Boy Tell ‘Em” Way but ultimately would leave his focus on rap to build an acting career – culminating with a leading role on Law & Order: SVU.

He is quoted as saying, “I can’t act. I really can’t act. I ain’t no rapper. It’s all game. I’m just working these niggas.”

5. Ol’ Dirty Bastard

Russell Tyrone Jones (known by his stage name Ol’ Dirty Bastard) was downright filthy. One of the founding members of the Wu-Tang Clan, O.D.B. was noted for his trademark microphone techniques and his outrageously profane, free-associative rhymes delivered in a distinctive half-rapped, half-sung style. His stage name was derived from the 1980 martial arts film Ol’ Dirty and the Bastard, the relevance of which was articulated by Method Man’s assertion that there was “no father” to Jones’ style.

After establishing the Wu-Tang Clan, Ol’ Dirty Bastard went on to pursue a successful solo career. However, his professional success was hampered by erratic personal behavior (he was shot on multiple occasions and at one point changed his name to “Baby Jesus”) and frequent legal troubles (second degree assault, attempted robbery, attempted assault, failure to pay child support, DWI and multiple counts of drug possession) including incarceration.

Ol’ Dirty Bastard died in late 2004 of an accidental drug overdose, two days before his 36th birthday.

6. 50 Cent

Born on July 6, 1975, in South Jamaica, Queens, Curtis James Jackson III (better known by his stage name 50 Cent) began drug dealing at the age of twelve during the 1980s crack epidemic. After leaving drug dealing to pursue a rap career, he was shot at and struck by nine bullets during an incident in 2000. After releasing his album Guess Who’s Back? in 2002, Jackson was discovered by rapper Eminem and signed to Interscope Records. With the help of Eminem and Dr. Dre, who produced his first major commercial successes, Jackson became one of the world’s highest selling rappers with the albums Get Rich or Die Tryin’ (2003) and The Massacre (2005). In 2003, he founded the record label G-Unit Records, which signed several successful rappers such as Young Buck, Lloyd Banks, and Tony Yayo.

Jackson’s fame, talent and toughness aside, is due in large part to the fact that he’s constantly beefing. 50 Cent has somehow found space in his schedule to engage in feuds with a slew of other rappers including the Wu-Tang Clan, Ja Rule, Fat Joe, Jadakiss, Cam’ron, Rick Ross, and former G-Unit members The Game and Young Buck, among others – all while still performing and even acting.

7. Lil’ Kim

Kimberly Denise Jones (a.k.a. Lil’ Kim) was born and raised in Brooklyn, living much of her adolescent life on the streets after being expelled from home. Influenced by fellow rapper The Notorious B.I.G. (with whom she carried on a brief affair), Kim began her music career in 1995 with the group Junior M.A.F.I.A. In late 1996, her solo debut album Hard Core was released. Hard Core was certified double platinum and spawned chart-topping hits “No Time” and “Crush on You.” Her following albums, The Notorious K.I.M. (2000) and La Bella Mafia (2003), both were certified platinum by the RIAA.

On March 17, 2005, Kim was convicted of three counts of conspiracy and one count of perjury for lying to a Federal grand jury about her friends’ involvement in a 2001 shooting outside the Hot 97 studios in Manhattan. She was sentenced on July 25, 2005 to a one-year and a day in prison, thirty days home detention upon release from custody, and three years of probation. She served the entirety of her sentence at the Federal Detention Center in Center City, Philadelphia. During her incarceration, her fourth album The Naked Truth hit the shelves.

Lil’ Kim was released from prison on July 3, 2006, after serving approximately 10 months, and returned to the public spotlight in 2009 with an appearance on Dancing with the Stars.

8. Jay Z

Originally from Marcy Houses housing project in the Bedford-Stuyvesant neighborhood of Brooklyn in New York City, Shawn Corey Carter was abandoned by his father and, at the age of 12, he shot his brother in the shoulder for stealing his jewelry. Needless to say, the young boy who would grow to become Jay-Z—one of the most financially successful hip hop artists and entrepreneurs in America—got his start scoring scratch by slinging rock on the street.

From the beginning of his professional recording career, when no major label gave him a record deal, Jay-Z, Damon Dash, and Kareem Biggs created Roc-A-Fella Records as their own independent label. After striking a deal with Priority to distribute his material, Jay-Z released his 1996 debut album Reasonable Doubt. The album reached number 23 on the Billboard 200 and was well received by critics.

After reaching a new distribution deal with Def Jam in 1997, Jay-Z released his follow-up In My Lifetime, Vol. 1. It sold better than his previous effort. Then, in 1998, Jay-Z released 2 Albums: Vol. 2… Hard Knock Life, which spawned the biggest hit of his career at the time, “Hard Knock Life (Ghetto Anthem),” and Vol. 3… Life and Times of S. Carter, which sold over 3 million records. Around that same time, Jay-Z was accused of stabbing record executive Lance “Un” Rivera for what Jay-Z perceived was Rivera’s bootlegging of his album Vol. 3… Life and Times of S. Carter. The stabbing allegedly occurred at the Kit Kat Klub, a now defunct nightclub in Times Square, New York City, on December 9. Jay-Z’s associates at the party were accused of causing a commotion within the club, which Jay-Z allegedly used as cover when he supposedly stabbed Rivera in the stomach with a 5-inch blade.

Jay-Z initially denied the incident and pleaded not guilty when a grand jury returned the indictment. Jay-Z and his lawyers contended he was nowhere around Rivera during the incident, and they had witnesses and videotape evidence from the club that showed Jay-Z’s whereabouts during the disturbance. Nevertheless, he later pleaded guilty to a misdemeanor charge that resulted in a sentence of three years probation.

Like every rapper on this list, Jay-Z had his squabbles. In 2001, he spoke out against Prodigy and performed a song “Takeover” at Summer Jam, which attacked Prodigy and revealed photos of Prodigy dressed like Michael Jackson. A line at the end of “Takeover” also referenced Nas, who criticized Jay-Z on “We Will Survive.” Nas responded with a diss track called “Ether” and almost instantly, Jay-Z added a verse to “Takeover” continuing to dis Nas.

But I doubt any of that bothers Jay-Z. Like one of his chart-toppers attests to, Jigga might have 99 problems, but a bitch ain’t one. He’s currently married to (occasionally blonde) bombshell Beyonce.

READ: Hollywood’s 10 Most Sensual Blonde Bombshells – #7 Beyonce

9. Lil Wayne

At the age of nine, Dwayne Michael Carter, Jr. (a.k.a. Lil Wayne) joined Cash Money Records as the youngest member of the label. In 1999, Lil Wayne released his Platinum debut album Tha Block Is Hot, selling over one million copies in the U.S. Although his next two albums were not as successful, Lil Wayne reached higher popularity in 2004, with Tha Carter, and in 2005, with its sequel Tha Carter II. His most successful album, Tha Carter III, released in 2008, went on to sell over 1 million copies in the U.S. its first week of release. It included the number-one single “Lollipop” and won the Grammy Award for Best Rap Album.

A renowned pothead and purple drank addict, Wayne has been repeatedly arrested for use or possession of drugs. On July 22, 2007, Lil Wayne was arrested in New York City following a performance at the Beacon Theatre. The New York City Police Department discovered Lil Wayne and another man smoking marijuana near a tour bus. After taking Lil Wayne into custody, police discovered a .40 caliber pistol on his person. The gun, which was registered to his manager, was in a bag located near the rapper. He was charged with criminal possession of a weapon and marijuana and was eventually sentenced to a year in prison, which he served in Rikers Island.

Wayne was released from prison after serving 8 months and was immediately placed on 3 years probation as the result of a separate drugs and weapons case in Arizona that had occurred in 2008, prior to the NYC gun charges.

10. Eminem

Marshall Bruce Mathers III quickly gained popularity in 1999 with his major-label debut album, The Slim Shady LP, which won a Grammy Award for Best Rap Album. This would be the first of three such Grammy Awards, as well as an Academy Award for Best Original Song, garnered by Eminem, the best-selling artist of the last decade. Needless to say, when it comes to music, the man can be considered a genius. But then again, his skill could also be attributed to his rocky relationships and past problems, which he raps about relentlessly in his songs. Go with what you know, they say, and that’s precisely what he’s done. The subject of much scrutiny, both as a rapper as well as in his personal life, Mathers has twice been married to his high school sweetheart who sued him for defamation (his own mother also sued him for slander), battled drug problems, and been arrested on numerous occasions for everything from assault to weapons charges. Sufficed to say, Eminem’s art is his life, and his life is fraught with scandal.

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Ryhme Animal – The Jump Off Bum Rush – Dreams Is Visions

Watch more episodes of the hip hop horror series RHYME ANIMAL

Dan Berry began writing and performing stand-up comedy while skipping class and drinking heavily at New York University. An inexplicably instant success, he has since appeared in clubs and on college campuses nationwide and is frequently featured on radio and television. Aside from creating the humor site “Jotter of a Rotter” and the internationally acclaimed website “The Prison Kite,” Dan has also lent his warped writing skills to a pair of failed pilots for FX and NBC, as well as to several current network shows that are somehow proving successful in spite of his crazed contributions.

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Must Reads 7/30/2014