The 50 Worst Hip-Hop Fails

Fail Occurred: 9/3/2009

This was big: The NY Daily News actually ran a positive story about hip-hop. Repeating what she had originally told for the BEEF documentary cameras, Roxanne Shanté, the famed 1980s MC, revealed to the newspaper that-after retiring from music-she had matriculated and studied until she had earned a doctorate degree. The best part, she said, was that her record label had paid for it all! The worst part, though, was that the whole thing was a lie, especially the "getting a doctorate" part, as uncovered in an article on Slate. So much for a positive story.

Fail Occurred: 9/10/1998

Canibus, while winning his ongoing feud with LL Cool J, took an L of his own upon showing up to the 1998 MTV VMAs. On the arm of Wyclef Jean, there to perform his verse on the "Gone To November (Remix)," Canibus arrived on the red carpet looking like he was dipped in the same silver paint bucket that Sisqo used to color his hair. On his 2003 song "My Name is Nobody," Canibus raps, "To this day, if someone asks me, 'Why were you silver on MTV?' I have to just tell them it wasn't me, 'cause I'm nobody." Yup.

Fail Occurred: 1/12/2007

He being a CEO-slash-rapper, Jay-Z felt too big to respond to outright disses from the Dipset collective. So, he sent his newest Roc La Familia protegé, Tru-Life, into battle; a pawn, at best. Tru aimed high, putting out Tru York, a mixtape remembered only for the artwork: a Photoshopped Jim Jones in a Borat-style thong and Cam'ron as a Seventh Avenue transsexual hooker. Retaliation came quickly and nerdily. Tru's MySpace was plastered with a new cover, one for Jim York that featured Tru and Jay-Z where Dipset had once stood. Also, a fake message was sent out to his MySpace friends (2007!), with a fake Tru apologizing for disrespecting Dipset. The excuse? He was just "broke," "dust smoking," and bored from driving his "96 Windstar Caravan."

Fail Occurred: 6/26/2001
Having built their career on aggressively underground and elbows-out aggression, M.O.P. would be an odd fit for any pop collaboration. Crooning à la 98 Degrees? That's not what the Mash Out Posse does. Which is what made "Life Is Good," their collaboration with the Lyte Funky Ones on the Dr. Doolittle 2 soundtrack, so strange. If 98 Degrees was the bootleg Backstreet Boys, then LFO was truly the bottom of the boy-band barrel, the type of cornballs that Justin Timberlake probably clowned while getting his tips frosted. Over a track that would seemed like Sugar Ray-lite (as if that were possible), M.O.P. member Billy Danze yells, "It's hard to sleep at night with a guilty conscience." Wonder how he's sleeping now.

Fail Occurred: 6/25/1996

As David Silver on the original Beverly Hills 90210, Brian Austin Green tried his hand at rapping and DJing. Remember: that was a TV show. Fake. Well, in 1996, the grown-up Brian Green (no Austin) decided that it wasn't just his character's passion-it was his own. With The Pharcyde's Slim Kid 3 making the beats, Brian Green dropped his album One Stop Carnival...with a thud. Now, Brian Green has (well had, at least) Megan Fox on his arm, while Tre has this garbage/footnote on his Wikipedia page (at least he got to snuggle with the bindi-wearing white girl on The Real World: Hawaii, too).

Fail Occurred: 4/23/2009

While spending the day at Rutgers University, white stoner-cum-white rapper Asher Roth was, pardon the phrase, riding high. In that mindset, he tweeted, "Been a day of rest and relaxation - sorry twitter hanging with nappy headed hoes." He thought he was making fun of Don Imus; just about everyone else saw it as a retread of an ugly moment in time and race relations. The reaction was swift. His words were recycled and re-tweeted, and anger brewed up and down RSS feeds. Taste-making hip-hop site Nah Right banned Asher, and was criticized for not doing so earlier. After a few hours, Asher finally gave a fearful apology. No one's ever said it's easy being male, middle-class, and white.

Fail Occurred: 12/10/2011

"Tatt my fuckin' name on you so I know it's real," Drake says on his song "Free Spirit." Months later, some girl committed hard to the statement, paying Los Angeles—based tattoo artist Kevin Campbell to give her the Nathaniel Hawthorne treatment and print DRAKE in big block letters across her forehead. Nothing lasts forever except for tattoos and regret and no amount of tears will get that ink off. But this story doesn't end with some poor girl getting her face ruined: Campbell became an entertaining interview, calling Drake a "goofnugget." Drake responded that he'd "fuck that guy up." Campbell offered "any time, any place." But in the end they squashed it and nobody got hurt.

Fail Occurred: 10/18/1991

Despite having the same cinematographer as Schindler's List, Vanilla Ice's star-killing vehicle Cool As Ice did not win any Oscars. In fact, it might be the worst movie ever, a bitter end to Rob Van Winkle's 12-month career death knell. Just as Ice was becoming a music superstar and signing all sorts of crazy multi-picture deals with Hollywood studios, certain contested "facts" about his biography were making him the laughingstock of the music world, even outside of hip-hop. By the time his big-screen debut finally hit theatres (opening at a dismal #17), even his clueless suburban female fans couldn't take his hilariously cheesy James Dean impression seriously.

Fail Occurred: 4/12/2010

Immediately after a 10-year stint in prison and a quick deportation to Belize, Shyne was met by Def Jam executive L.A. Reid, who announced that he'd signed Shyne to a $1M contract. Congratulations! Unfortunately, Shyne-sick of deep-voice comparisons to Biggie-has decided to change up his vocals, so that he sounds like you'd imagine Biggie to sound like...if he sucked. Well, that's $1M down the hole to wherever Shyne's voice is coming out of. A word to L.A. Reid: just because something's been in the box for ten years doesn't mean its still in mint condition.

Fail Occurred: 6/1991

It's common knowledge that women don't buy Playgirl magazine. In 1991, Big Daddy Kane was approached to pose for Playboy's gay cousin. What followed were pages and pages of Big Daddy Kane doing an impersonation of the "Dick in the Box" video, fifteen years before there was a "Dick in the Box" video: John Lennon glasses, flat-top hair, and beige suits. (Big Daddy's cane was hidden from the cameras by silk boxers and bite-sized chocolate candies.) His come-hither bedroom eyes? Not a good look.

Fail Occurred: 1992

Main Source was about as much of a group as the Cavaliers are a team. That is, there was only one guy putting any points on the board, and no one really knew what the fuck the other guys were doing. Large Professor was making all the beats and writing/performing all the raps on their classic debut Breaking Atoms. So what were literal, not figurative, brothers Sir Scratch and K-Cut doing? Um...wowing the world with their renowned Canadian dual DJ sets? Right. So it would make total sense that their Mom-ager, who oversaw the group's finances, would screw Extra P out of paper and force the group's only talent to look at the front door, right? The non-rapping, non-producing DJs, who kept the Main Source name, went on to recruit New Music Seminar phenom Mikey D and make one of the worst sophomore albums ever before receding back to the frozen fortress of solitude that is Canada. Apparently, Professor is not the word to play.

Fail Occurred: 5/12/2008

Suge Knight has always been considered a man to fear. The former bodyguard, UNLV linebacker, and Piru banger would get what he wanted by any means necessary (ask Vanilla Ice...or Pac?) That all changed when, while at the club Shag in Hollywood, Greg "The Barber" laid Suge out. The pictures, leaked to TMZ, showed a bloodied and unconscious Suge, looking strikingly similar to a beached whale as he took up a good deal of sidewalk space. When it was revealed that Greg "The Barber" is of average height and weight, it gave hope to everyone who steers clear of the gym, should Suge Knight ever approach. We're not one to wish violence on a man, but seeing the tables turned on Sugar Bear was the most satisfying sight since Deebo got knocked the fuck out.

Fail Occurred: 7/21/2001

After four years of self-imposed silence, following The Miseducation of Lauryn Hill, Lauryn Hill was to make her grand return on MTV's rebooted Unplugged. One of her opening lines, "I used to be a performer, but I don't really consider myself a performer any more." Yeesh. Buckle up, because this joyless ride is going to get bumpy. Emotional, rambling, and generally strange, MTV Unplugged 2.0 (how is that really the name of this album?) is a freak show: Spanning two disks, L-Boogie participates in lengthy monologues, speaking on her religious conversion, her state of being, her life changes. Between Lauryn's clumsy guitar-playing and nonsensical raps, the long-awaited new songs sounded like disappointing demos. You expected to hear the hits? You must've been miseducated.

Fail Occurred: 1/13/2011

Gucci Mane has been knocked down a number of times during his career, but this year he finally Mike Tyson'd himself. Fresh off another jail bid, the rapper known for his "Brrr" ad-lib stopped by his friendly neighborhood tattoo artist and had an ice cream cone inked onto his face. With three scoops. And red lightning bolts firing out of the dessert. Oh, and the word "Brrr" underneath. Pictures of the face-tat immediately went viral, with everyone from fans to detractors to Gucci's own record label execs wondering if they were real. They were. When we asked Gucci why he got it he responded saying, "Because I'm the coldest MC in the game." Umm, okay.

Fail Occurred: 10/24/2006

It was a beef that never really picked up steam. Gillie Da Kidd, a no-hit Philadelphia rapper, claimed that an increasingly popular Lil Wayne had stolen his style, and-now that Weezy was getting famous-Gillie deserved the credit for his success. Bo-rrrring. So, Gillie leaked a picture of Lil Wayne kissing Baby (a.k.a. "Daddy"), a photo that had every blogger posting and every commenter SMH-ing. Alas, in all the hubbub, everyone forgot about Gillie. As for why they were kissing, Baby ("Daddy") explained saying, "It's a Mafia thing." Something no one really bought.

Fail Occurred: 7/27/2009

In life, there are only two things that last forever: tattoos and regret. Last summer, Crooked I took that sentiment to heart-or more accurately, to his forearm. After going to the tattoo artist Shade, Crooked I-a member of the rap collective Slaughterhouse- emerged with the made-up word SLAUGTER vertically inked into his skin, forever. (A half-assed fix by Shade would run HOUSE alongside the original misspelling, the two lines sharing one H.) As Homer Simpson said, "I am so smart! I am so smart! S-M-R-T, I mean, S-M-A-R-T!"

Fail Occurred: 11/18/2003

On November 18, 2003, Ray Benzino-owner of The Source, failed rapper-played audio that he claimed would destroy Eminem, who had become something of an obsession for him. On the tape, a demo from 1988, Eminem-white rapper that he is-used the N-word on two separate songs. Unconscionable. His excuse that the songs were recorded out of anger at a black ex-girlfriend doesn't explain why he'd say, "All the girls I like to bone have big butts/No they don't, 'cause I don't like that n*gger shit/I'm just here to make a bigger hit." He also blamed it on being young and stupid, which makes more sense. "Stupid" is exactly right. The shocking revelation remains the only stain on the reputation of the musical genius.

Fail Occurred: 1994-2005

This is going to sound strange to younger readers, but The Source used to be a really important magazine! (A magazine was like a bunch of Wikipedia pages that came to your house once a month.) Dave Mays and perpetually desperate wannabe rapper Benzino co-owned The Source, but Benzino ran the magazine as if it were a soapbox to stand on. While Mays was managing his Boston group the Almighty RSO, Benzino attempted to force the staff into giving RSO positive coverage. (They quit, instead.) In '99, an anonymous critic wrote up Zino's new group, Made Men, giving them four and-a-half mics for their album; a classic. By the time he started his obsessive beef with Eminem-via print and radio airwaves-all of The Source's cred had fallen out the window. The Source lost advertisers, subscribers, access to Universal Music Group artists, and-after filing for bankruptcy-it finally lost Benzino.

Fail Occurred: 9/27/2001

In 2001, after coming back from a video shoot, Erick Sermon fell from a third-story window. While he had originally told authorities that his injuries were caused by a car accident, police began investigating it as a suicide attempt as a result of jumping out of a woman's apartment in New Jersey. Gay rumors spread soon after. The fail isn't that there were gay rumors about Erick Sermon (they are gay rumors about nearly every popular rapper) but that he couldn't explain a simple accident which only made the story more and more bizarre. Erick Sermon denied everything, and continues to deny everything. Related: Since the fall, consumers have denied everything he's put out.

Fail Occurred: 1999

So dirty. So clandestine. So good. "Linda Trip," Company Flow's takedown of rival underground rapper Sole from the Anticon crew, featured excerpts from a secretly recorded phone conversation in which a pathetic Sole professes his admiration for Company Flow, after he'd already dissed them. The red-haired MC from Maine said, wide-eyed and earnest, "You know I like your shit. I don't want to be against you guys. I want to be down. I love Company Flow." El-P's rapped response? "I feel like Selena—the president of my fan club is trying to kill me!"

Fail Occurred: 2011

V-Nasty is a half Vietnamese half-white girl from Oakland representing her crew, the White Girl Mob. She defends her right to use the N-Word freely in her everyday conversation. It's okay, she assures us, because "it ain't no color in Oakland." She's on "some real n***a shit" she adds. Oh, and haters have never walked in her shoes. On her latest album she said she was trying to stop using the word, but accidentally used it anyway. The question isn't "Will this end well?" but "Will this please end?"

Fail Occurred: September 2007

September 11, 2007 pitted Kanye West and 50 Cent against one another in what turned out to be the most hyped sales battle in hip-hop history. That it was even possible for Kanye to beat 50 seemed unbelievable; a shift in the winds had moved fans away from bloody gutters-and-Lugers fantasies and toward Big Brother lovefests. The Battle of Billboard showed 50 to be vulnerable in a way that he never was before; news broke of him handling record-label frustrations by throwing a plasma TV through a window and into the street below. 50 Cent, who had threatened to quit rapping if he lost, lost. (While some would argue this point, 50 is still rapping.)

Fail Occurred: 5/9/1989

Strange for a radical and militant hip-hop group but, with the release of Spike Lee's joint, Do The Right Thing, Public Enemy had become really popular. So, their statements-good and the bad-were taken pretty seriously. Professor Griff, the group's "Minister of Information," infamously gave an interview to The Washington Times, saying, "Jews are responsible for the majority of the wickedness in the world," and various other Nazi and/or Nation of Islam clichés. After an uproar in the media, Russell Simmons called Griff "a racist stage prop" and he was booted from the group. Sadly, this was still Professor Griff's biggest contribution to Public Enemy, as the controversy overshadowed their music at a crucial time in their career.

Fail Occurred: 1985-PRESENT

After surviving at least two Transformer chain-snatchings, a drunken (and televised!) bicycle accident, and a fight on the wrong side of Maino's hand, Yung Berg is still...Yung Berg. One has to wonder why Yung Berg bothers getting up every morning if he's going to get beaten up every afternoon.

Fail Occurred: 1999-PRESENT

What's the line? "Plastic surgery is a helluva drug?" Where hip-hop's greatest sex symbol of the '90s once was, now stands the Teddy Ruxpin doll in drag.

Fail Occurred: 3/21/2006

In May 2005, Game had a butterfly-wings spread-tattooed beneath his right eye, a signifier of "new life." He had just donated $500K to Compton's schools, and was looking to spread positivity. Everything was fine until people made fun of him because, you know, he's a rapper and rappers aren't supposed to have butterfly tattoos on their faces. So, he got the Dodgers' LA logo drawn over it, since (as he said), "I woke up one morning and I was on my shit like I usually be, and I felt like I was the face of L.A. So I went to the tattoo shop and put LA on my face." He later slapped an ugly red star into the mix because you could definitely still see part of that fuckin' butterfly. Yeah, this guy definitely has a tramp stamp.

Fail Occurred: 12/2001

You know the story-in the midst of their beef, Jay-Z made a song called "Super Ugly" where he finally revealed that he had been giving Nas' baby's mother Carmen the business. Pretty crazy move, right? Well, the day after debuting the controversial track (and losing an impromptu listener's poll), Hov returned to Hot 97 with an unusual mission: to apologize. According to a bashful Jay, his mother, Gloria Carter, told lil' Shawn that crossing the no-women-and-children line was in "poor taste," compelling the 30-something rapper to say, "I'm sorry." The unprecedented move (there's no apologizing in rap!) gave legions of Nas Stans more than enough reason to claim victory on behalf of God's Son.

Fail Occurred: 12/26/1993

Leading up to that fateful night in January of 1992, KRS-One was experiencing a bit of a backlash. Ice Cube had dissed his positivity. X-Clan had chided him for supposedly selling out. It was at this moment that Prince Be of P.M. Dawn-a hip-hop/R&B duo known for soft hits and wet whispers-told Details Magazine, "KRS-One wants to be a teacher, but a teacher of what?" Wrong move, friendo. A week later, during an MTV-filmed show at NYC's Sound Factory, PM Dawn found themselves on the wrong side of KRS-One's Boogie Down Productions crew. In what was originally intended by BDP to be an impromptu battle of mics turned into a melee, with P.M. Dawn literally being thrown offstage. To cap it all off, KRS-One snatched the mic and performed "I'm Still #1" to a riotous crowd. "I answered his question," KRS-One later told USA Today. "I'm a teacher of respect."

Fail Occurred: 4/26/2006

Even before getting his SAG card to portray The Notorious B.I.G., mixtape-rapper Gravy had a history of acting. In a desperate attempt to up his street cred, Gravy allegedly had one of his friends shoot him in the butt (...) while entering Hot 97's studios, after which he proceeded to do a Funk Flex interview while bleeding. The official police report said that a member of his entourage shot him after getting mad that he wasn't allowed to come inside the studio. Gravy told the cops that "he fell," which in hindsight, sounds about right. A Hot 97 ban led to Gravy (the rapper) never being heard from again.

Fail Occurred: 4/8/2013
No one's questioning LL Cool J's legacy, especially after comfortably situating himself as one of the best rappers ever. However, his embarrassing inclusion on "Accidental Racist" is a setback that even the Queens MC can't justify. The record starts out innocent enough, with country singer Brad Paisley pandering to his wholesome audience over serene guitar strums. Unbeknownst to the listener, LL bursts in around the four-minute mark with, "Dear Mr. White Man, I wish you understood/What the world is really like when you're living in the hood." Yikes. Topping off the performance with lines like, "If you don't judge my gold chains/I'll forget the iron chains" and "Feel like a new fangled Django, dodging invisible white hoods," makes this a series of hip-hop quotables for all the wrong reasons.

Fail Occurred: 6/28/2001

The Summer Jam Screen (n): a showcase for derision; unwanted exposure-i.e., "Don't make me have to put you on the Summer Jam screen." Prodigy, one-half of Mobb Deep, had been tossing subliminal one-liners in Jay-Z's direction for years, but Jay-Z didn't respond until he took the headlining spot at Hot 97's annual supershow in 2001. Jigga pulled a rap-beef coup d'état when he projected a childhood photo of Prodigy in tap-dancing regalia: toes pointed to the ceiling, smile pointed at the camera, an indelible image to backup "Takeover": "When I was pushin weight, back in '88/You was a ballerina, I got the pictures, I seen ya!" The irony of Michael Jackson coming out during Jay-Z's same set was lost on everyone, though that's because Michael Jackson had never successfully come off as a gangster. The power move made P quietly obsessed (Infamy might be the most passive-aggressive album of all time), and threw Mobb's '90s musical winning streak off course.