The Dead End Theory: 15 Rapper Relationships That Ended In Break-Up

From Eminem and Mariah Carey's bittersweet triste to Darlene's immortal gangsterism, and the Kelis and Nas shakedown, HipHopDX looks back at some high-profile Rap relationships.

While Love and Hip Hop is currently a hit reality show, the pairing of those two terms is far from new. Whether we admit it or not, Hip Hop has always loved a gossip story just as much as it's loved a good old fashioned romance. Rappers canoodling with rappers, actors, models, and other celebs, has always provided decent fodder when the music wasn't at the forefront. Of course the break-ups prove to be just as interesting as the make-ups sometimes. Over the last 25-plus years, as Hip Hop ascended to global mainstream success, the private lives of its stars have also become public interest. That makes the "behind the scenes" info all the more interesting, learning about the reasons behind certain songs, interviews, and appearances in music videos. As Cupid shoots his arrow over this week, HipHopDX collected some of the most memorable couples. Some of these love affairs ended amicably, while the pain of others still echoes on. Regardless of the result, Hip Hop enjoys a good love story, even if its about the absence of it.

Diddy & Jennifer Lopez (circa 1999-2001)

J-Lo made a dazzling appearance in Diddy’s (then "Puff Daddy") 1997 video for “Been Around The World.” In the months to come, the two began to appear as a power-couple in Hip Hop that rivaled Jay-Z and Beyonce 10 years later. However, the 1999 New York City club shooting not only sent Shyne away, it cast away Cupid. Reportedly traumatized by lifestyle of “makin’ moves with Puff,” J-Lo left the Bad Boy Records mogul in early 2001 for a notorious string of botched relationships.

Ice-T & Darlene Ortiz (circa 1984 - 2000)

In J-Zone’s just-released book Root For The Villain, the producer/emcee reveals that he discovered sex by way of Darlene Ortiz’ scantily-dressed appearances on early Ice-T singles and albums. The couple were as real to life as Ice’s street account rhymes, staying together for a reported 16 years before Nicole "Coco" Austin entered the picture. Darlene may have been the first “Hip Hop honey,” and that's powerful.

Kanye West & Amber Rose (circa 2008 - 2010)

Kanye West, having just left a relationship with former fiance Alexis Phifer, tore up the red carpet with the buxom Philadelphia dancer/model/video vixen Amber Rose in 2008. The pair’s relationship was a phoenix in 808’s & Heartbreaks and carried Kanye, past the Hennessey-induced Taylor Swift VMA incident, to the early recordings of My Beautiful Twisted Dark Fantasy, parts of which Amber is rumored to have inspired. Now Wiz Khalifa’s “wifey,” Rose’s presence in the industry outlasted her relationship with one of its premiere artists.

Kool G Rap & Karrine “Superhead” Steffans (circa 1995-1998)

One of the greatest lyricists of all-time was the one who was the first notable significant other to the legendary '90s-'00s video vixen, Karrine "Superhead" Steffans. The pair later had a child, as Karrine was with the emcee during his relocation to Arizona, in the Roots Of Evil-era. The relationship didn't last, as Superhead cited a physically abusive G Rap in her memoir, and she continued in a string of relationships, including comedian/television host Bill Maher. As for Giancana, he ended up with veteran underground emcee Ma Barker, who the rapper recorded Click of Respect with in 2003.

Treach & Pepa (circa 1998-2001)

Old school Rap royalty's power-couple, Naughty By Nature's Treach and Salt-N-Pepa's Sandee Fenton maintained a marriage towards the end of both group's limelight runs. They even tattooed their rings on their fingers to prove their love was everlasting. With a few children, a long history of abuse and a divorce that still echoes to this day, this marriage was one of Hip Hop's most popular for more reasons than one. These two are a prime example of how tattooing for love's sake can result in a total disaster.

KRS-One & Ms. Melodie (circa 1988-1992)

Another old school union. This one stayed larger under wraps, though the two Stop The Violence Movement rappers have not been together in some years. KRS-One clearly maintains his seat at the table as one of Hip Hop's biggest trail-blazers, educators and late '80s, early '90s hit-makers. After Boogie Down Productions dissolved to KRS' solo career in the early '90s, the marriage reportedly went with it. The Brooklyn native older sister of another BDP affiliate Harmony only released one album, Diva. If the title was true, perhaps that was a factor in the break-up.

Eminem & Mariah Carey (circa 2001-2002)

The union between Eminem and Mariah Carey was one of those affairs where the events of the public breakup outlived the actual romance. The two were rumored to be dating as early as 2001, when Em was supposed to lend some bars to M.C.'s Charmbracelet. Instead, he shouted her name out on some tracks (every rapper did at some point though). Then Eminem confirmed the rumors to Rolling Stone in a backhanded sort of way (as in, yes, they dated, but he didn't like her). Mariah later tells Maxim nothing happened, and before you know it Mariah is dedicating whole songs to Em (i.e. "Obsessed" and random shots earlier on "Clown"), Shady replays voice-mails, and it all went downhill from there. Seven years of bickering for what sounds like a two-day relationship...

Nas & Kelis (circa 2005-2009)

Rumor has it when Nas first met Kelis, he said he was going to marry her. Destiny fulfilled, as the two tied the knot in January of 2005. While the pair was very out in the open about their relationship (Nas even played the short-order cook in Kelis' "Milkshake" video), the marriage only lasted four years. In April of 2009, Kelis filed for divorce while she was seven months pregnant with their son Knight. It was finalized a little over a year later, with Nas coughing up $55,000 in monthly child support. Nasir might have predicted their marriage, but did he predict how it would end?

Mack 10 & T-Boz (circa 1998-2004)

When Mack 10 was one of the few gold-selling stars of the West Coast, running Hoo Bangin' Records, he snagged the still-single member of TLC in T-Boz. The couple stayed strong as Mack headed to Cash Money Records for a brief stint, and a West Side Connection follow-up. With a daughter born in 2000, the couple began to have problems several years later. T-Boz filed a restraining order against the Inglewood, California rapper at the same time his platinum super-group distanced themselves. This has long led to speculations of abuse in a relationship that was good when the times were good.

B-Real & Carmen Electra (circa 1994-1998)

Another West Coast relationship of note was Cypress Hill front-man B-Real's years with then-Singled Out host Carmen Electra. Although B was essentially going where Prince had been, the pair maintained years together as a Hollywood power-couple operating in different worlds. While Carmen later appeared in Playboy, was a Baywatch cast member and the it-girl of the mid 1990s, B-Real released two highly successful albums in Cypress Hill III: Temple Of Bloom and Cypress Hill IV. Like the joints, sometimes love burns out.

Nas & Carmen Bryan (And Jay-Z too) (circa 1999-2001)

"Because you know who did you know what with you know who / but let's keep that between me and you (for now)." The line heard round the world, found on Jay-Z's "Takeover." Nas' baby mama Carmen Bryan was an early love of the veteran emcee. What the Queens rapper didn't know was that he was sharing her with his Brooklyn archnemesis. That's never a good feeling, especially when Jay-Z revealed even dirtier details of ejaculating on Nas' daughter Destiny's carseat. Now that Jay has a daughter of his own, he probably regrets telling that story, but for those who want to relive that saga, Carmen has her book It's No Secret: From Nas to Jay-Z, from Seduction to Scandal - a Hip-Hop Helen Of Troy Tells All. Oh, Troy.

Erykah Badu & Andre 3000 / Erykah Badu & Common / Erykah Badu & The D.O.C. (circa 1994-2004)

The current lineup is Erykah Badu and Jay Electronica (as far as we know), but there's an urban legend that Fatbelly Bella has some sort of magical power over rappers. The legend goes even further to say that Erykah Badu ruins fashion choices for her mates (Andre 3000 started rocking pink furry pants from that point on, then Common had that Electric Circus period). While the two major romances of Erykah Badu were Andre 3000 (shared a child named Seven together and when they broke up, 3000 penned "Ms. Jackson" as an apology to Erykah's mom) and Common (publicized in the video for "The Light"), she also has a child with The D.O.C. named Puma. Now she and Jay Elec have a daughter named Mars. One thing is for certain, Erykah's kids will probably all be talented musicians, wearing very odd clothes.

Ad-Rock & Ione Skye (circa 1992-1999)

The Beastie Boys' Ad-Rock, who is anything-but-Lloyd Dobbler, snagged the it-girl from Say Anything, and the couple married in the early 1990s. The daughter of '60s singer Donovan is now with singer Ben Lee, who ironically was an act signed to the Beasties' Grand Royal label throughout the late '90s, early '00s. These days Ad-Rock eats his White Castle fries with onetime Le Tigre front-woman Kathleen Hanna.

Da Brat & David Guest (2006)

No words. Not just because it was one pap's lucky snap. We were Da's Guested.

50 Cent & Vivica A. Fox / 50 Cent & Chelsea Handler (circa 2003, 2010-2011)

Nothing was more awkward than watching Vivica A. Fox drop it like it's hot for 50 Cent on stage at an award show in 2003 back when her career was about to blow up. Rumors of Fox (who was rebounding from a marriage to a Death Row Records singer) showing up at the film set for Get Rich Or Die Tryin' were only eclipsed by the rumors that these two were an actual item. It seemed as though Vivica pursued 50 Cent hard, whereas the flipside happened when Fif met Chelsea Handler. After showing up on her show Chelsea Lately in 2009 and asking if she had a boyfriend, 50 continued to chase the Chels until they eventually dated in public. Handler would TwitPic pics of Fif in her bed, have him show up for embarrassing show skits, and even got him to do a video with viral boy Keenan Cahill for "Down On Me." The results of both of 50's poor pairings? Well, Vivica showed up in 50 Cent's video for "Do You Think About Me" so they made peace; meanwhile Chelsea still references the 50 first dates and even told Howard Stern she dumped 50 Cent when he suggested a threesome with his other ex-girlfriend Ciara.

58 Comments

  • susan

    I had a problem with my boyfriend six months ago,which lead to us apart. When he broke up with me,I was no longer myself,I fill so empty inside sorry.Until a friend of mine told me about one of her spells that helped in same problem too. i email the spells and I told him my problem and I did what he asked me to briefly make. the long story Before I knew it what happened,not 48 hours,my friend gave me a call and he come back to me and told me he was sorry about what was going to happen, I'm so grateful to these spells and will not stop publishing his name on the internet just for the good work he has doing.If you need his help,you can email him at (UNIQUELOVESPELLCENTER@YAHOO.COM)and he will also help you to Dr.TRUST( UNIQUELOVESPELLCENTER@YAHOO.COM) I will be forever grateful to you.

  • Marian

    When my boyfriend and I broke up I was completely lost. A good friend of mine recommended that I have a love spell cast to bring him back by Oduwa Home of Solution. I thought that idea of a love spell was strange, but was willing to give it a shot. When I contacted Dr.Oduwa for the first time I was scared because I was not sure if what they did went against my religion. he assured me that they only use traditional voodoo which is safe and has no side effects. I felt a little better and decided to do the return lover spell. I did not think that it would work considering my ex and his whole family hated me and told me never to contact them again. Within 3days he showed up at my work and brought flowers to me. He said that he missed me more than he could describe and decided that the good out weighed the bad. We got back together and our relationship has been better the second time around. I have to give Oduwa home of solution all of the credit in the world for helping us get back to a better place than where we began. The new found love that he has for me is incredible and I cant wait to see what the future holds! he can also help you. his email is oduwahomeofsolution@gmailcom

    • Shell 3ee

      Just wait until that magic bites you in the ass and you decide that you don't want to be with him anymore and he becomes obsessed with you. You'll wish you wouldn't have messed around with that crap. Just wait until he's stalking you and breaking into your house in the middle of the night to watch you sleep. My advice? Figure out how to undo what you have done while you can.

  • bugatti

    when i was with vivca i thought i was onto something but the next week? nah it was nothing

  • Gunot

    Wait...I thought 50 was gay? i didnt know he went out with handler, i thought he was wit yayo who knew

  • JAY-Z

    Interesting article!! p.s. I have more than 18,500 Japanese-followers. If you need my promotions, check this out. http://bit.ly/zXEFnw

  • yoyoyoyo

    WHAT ABOUT KILLAH PRIEST & AMIL?? haha

  • Anonymous

    @ Anonymous: Not making excuses just pointing out the facts Nas made this clear years ago and though I didn't read her book Carmen even said the reason she got with Jay was to get back at Nas!!!!

  • gayassnigga

    Let's all take a guess on who will be Erykah Badu's next bitch? Could be one of them used-to-be-hard-in-the-90's-but-now-just-makes-conscious-wannabe-artistic-bullshit-rap emcees like Mos Def or Q-Tip. Or she could try out some of these new rappers. Imagine Erykah & Kendrick Lamar or Daytona

  • da1

    Haha he said Nas & Carmen Bryan (and Jay-Z too). Yeah that bitch was a bustdown

  • Anonymous

    what a stupid article. thanks for this bullshit dx

    • ETK

      why the fuck did you post then? you're giving the article more attention dumbass whiners these days, it's amazing really

  • jnr

    Da Brat and David Guest??? Ewwwww... YUCK! I'm going to throw up!

  • jnr

    What about Dr.Dre and Suge Knight having the same baby mama? SMH These rappers will never learn and yet they campaign for people to "wrap it up before you slap it up" when they are the ones having sex with each others partners and making babies out of it, wow... Talk about double standards!

  • Anonymous

    Em and Mc would have bin a power couple.

  • Anonymous

    JLo & Diddy was a good look but Erykah & Andre >>>>

  • Anonymous

    DX gave Electric Circus a 4. just sayin

  • BIlal

    Drake n Justin? http://i741.photobucket.com/albums/xx58/salasrcp90/drakekissingjustin.jpg?t=1328415609

    • Lil Wayne

      Aubrey Drake Graham its over! I loved you, I had plans for us and this is what I get? I should have never trusted you.

  • JPipe

    They should focus on the positive & the relationships that has lasted.

  • The Future

    Interesting article but like someone said before how can u forget about Big and Faith? What about KC & Mary J. Blige,Young Jeezy & Keyshia Cole and of course Lil Wayne and Trina? Also, yes Nas and Carmen dated Wayyyy before the date you gave. Nas had his daughter with Carmen in '94 and when Carmen found out he was cheating on her she hooked up with Jay out of revenge....Nas knew about it way before Takeover and he wasn't really trippin since he was messing with other women. Also, speaking of Nas....though Nas and Kelis married in '05....they started dated way back in'02.....remember shortly after they started dating Kelis was featured on Nas' God Son album on a track called, "Hey Nas"!!!!!

  • uptownfirst

    Big and Faith. How y'all forget that???

  • Anonymous

    I think dates of Nas and Carmen r wrong. wasn't his daughter born like around illmatic? he said by that time she was just his baby mams and he was already down w/ other women so they weren't really like that.

  • So Icy Boi

    Don't forget about Baby and Wezzy

  • Anonymous

    where's wayne&trina?

    • jnr

      Damn Trina was REALLY in the "streets" like that? Just like Eryka Badu! WOW... I'm speechless about these rappers sharing women and making babies out of it and yet they campaign to the public about AIDS? SMDH...

    • COLE WORLD

      and Buck and Trina? and Trick Daddy and Trina? and on and on and on...

  • CizzieB

    but of course this is just rappers

  • CizzieB

    You definitely forgot about Usher and Chilli.

  • Anonymous

    Eminem is a crack head idiot. How can u say u don't like a woman like MC ? She's a complete woman. Now some kid rapper is smacking the ass you were suppose to. Sad!

    • J-M-C

      I like the fact that he's stroke faced it makes him all the more creepier with his "evil" character. Dude is off drugs now and is a puppet in the industry so yeah.. I'd be afraid too. Still one of the illest

    • Anonymous

      eminem is a homo he blasts any woman hes ever been with in his music. called that black chick in high school a "nigger" killed KIM on his records dissed mariah carey and 10 years after they stopped seeing eachother was still making records about her guy is a closet fag. he's good friends with elton john and im pretty sure hes fucked dr.dre before and im being deadly serious stroke face druggie slave scared to stop making music cuz he thinsk jimmy ivoine will kill him

  • JC

    THEY FORGOT ABOUT DRAKE AND JUSTIN BIEBER FOR REAL!!! http://i741.photobucket.com/albums/xx58/salasrcp90/drakekissingjustin.jpg?t=1328415609

  • Anonymous

    yall forgot about birdman and lil wayne, but i guess they still together so that makes sense to leave them off

  • c mon man

    Badu musically is the shit! but its sort of hard to not consider her a h**

    • @Imani

      yes a hoe don't get confused by her so-called "blackcentrism" shit

    • Imani

      a hoe?? bc she had SERIOUS relationships with guys, who are known by more than their friends and family, hardly makes her a hoe...just shows the types of circles she runs with ...and that she has damn good taste

  • Anonymous

    lol @erykah the bitch's list goes on and on if we consider jay electronica's relationship and all the rappers who probably fucked her but without being revealed on public's eyes

  • 85live

    some real faggot TMZ shit here dx. ive come to expect nothing less. what about fonsworth bently and sean diddy combs? everybody knows they were fuckin. common looks like a gay pirate on the front page. erkah badu is a neo soul slut, how many kids she gonna hatch for these dirt bag rappers? what a beautiful lady.

    • @Anonymous

      since when making joke bout faggot people is presuming of any homosexual orientation ?? i don't get the logic of yours cause obviously there is none dayum faggot people are getting all over these hip-hop sites too right now to get their weirdo and gross life acceptable on public's eyes

    • Anonymous

      OD-ing on gay talk and gay jokes just makes you sound like youre in the closet.

    • Anonymous

      nigga does homosexuality run through your mind 24/7 or something? damn nigga no one likes you. just shut the fuck up.. obsessed with gay culture. we dont care nigga god damn

  • word

    Darlene > Coco You know Mack 10 abused T-Boz. Wack 10.

  • tido

    ICe-T : you mean 16 years?