Three Is Definitely More Than A Crowd: 15 Of The Messiest Celebrity Love Triangles

December 6, 2012  |  
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It’s tough being a celebrity. Why you ask? I mean how are you supposed to choose from the many, many attractive men and many, many smokin’ hot women who throw themselves at you? Easy, you can’t. Celebrities are only human, after all. And while their inability to keep their lust to themselves could cause some problems in their personal life, it provides endless entertainment for the rest of us. So for your viewing, thank God I don’t have all that drama going on, pleasure, here are 15 of the craziest celebrity love triangles.

Dimitri Halkidis/WENN

Faith Evans/Notorious B.I.G/Lil’ Kim

It’s one of hip-hop’s most storied tales, involving one of rap’s most revered stars. Faith Evans and the Notorious B.I.G. were two of the East Coast hip-hop scene’s most visible stars and one of its most powerful couples. So it came as quite the scandal when years after her husband’s tragic death, Evans revealed in her book “Keepin’ The Faith” that she once caught Biggie in bed with rapper Lil’ Kim.

“I stopped throwing punches for a minute to get a good look at the chick I was beating up,” she writes. “It was Lil’ Kim. She was completely butt-naked, yelling as I pushed her around the room.”

The feuding has continued long after Biggie’s death with the release of Notorious in 2009. Lil’ Kim was far from pleased with her portrayal in the movie, fanning the flames of an already tense feud.

Mashonda/Swizz Beatz/Alicia Keys

Who would have ever pegged Alicia Keys a hip-hop homewrecker back in 2010? Girl shouldn’t you have been bangin’ away on a piano instead of bangin’ away on something else? But we digress … Though, as in all love triangles, some of the specifics vary from party to party, one thing is certain: Mashonda’s open letter to Keys (after news of an impending divorce from Swizz Beatz and Keys little tweets of love were already being circulated) certainly summed up her feelings. Check out this excerpt:

My concern with AK is no longer the fact that she assisted in destroying a family but that she has the audacity to make these selfish comments about love and wanting to be with someone, even after knowing their situation. How is this the same Superwoman that I sang out loud with in my truck? I ask myself sometimes. If you are reading this Alicia, let me start by saying, you know what you did. You know the role you played and you know how you contributed to the ending of my marriage. You know that I asked you to step back and let me handle my family issues. Issues that you helped to create. Im not saying everything was perfect all the time but no relationship is perfect. We made a vow to God and I believe you should have respected that, as a woman. I know you owe me or my son nothing but I just wish you would’ve handled things more carefully. I’m not judging you, I put you and the whole situation in the hands of God, the Higher Power.


Karrueche Tran/Chris Brown/Rihanna

You knew we couldn’t help but toss in the lovely little love triangle of Karrueche Tran, Chris Brown and Rihanna. Obviously anything involving Brown and RiRi was going to be a disaster, but this drama was especially messy. So after “aspiring model” Tran sank her claws into Brown it wasn’t long before, you guessed it, RiRi came back into the picture. Sure, Breezy, ya’ll are just friends. Tran didn’t buy it either and started going back and forth with RiRi over Twitter. Soon Brown and Rihanna started getting all up in each other, culminating in a very awkward (at least for Karrueche) kiss at the MTV Video Music Awards. That was the last straw for this chick who prompted dismissed Breezy. In case someone hasn’t said it before: Congratulations and good work getting rid of the trash, Karrueche.

Ian Wilson/

Jennifer Aniston/Brad Pitt/Angelina Jolie

The big kahuna of all celebrity love triangles, the Jennifer Aniston-Brad Pitt-Angeline Jolie debacle of 2005 will go down as one of the most surprising developments in the annals of Hollywood history. After seven years together and nearly five years of marriage, Aniston and Pitt announced their divorce to the shock of fans and tabloids far and wide. While this could have been just another example of boring, first-world, rich people problems, then Ms. Jolie came to the rescue and spiced things up. Rumors began to swirl that the Mr. & Mrs. Smith costars were more than friends and, in fact, another kind of buddy to each other. Within a few months, Pitt and Jolie would shack up and the rest is multi-ethnic child, world-saving, verge-of-marriage history.

A. Miller/WENN

Amber Rose/Kanye West/Kim Kardashian

Not that we’re surprised that Kim Kardashian was involved in a homewrecking-like situation, we are surprised it took this long for it to happen … and surprised at whom it happened with. We would have almost definitely thought it would be between teammates or something. But regardless, Kardashian still managed to screw up a two-year romance between Kanye West and Amber Rose. Rose would later tell the New York Post that West “… is your typical rapper in the industry. He can’t be faithful, and it’s not just with one person. He’s just unfaithful with a lot of different women. I got to the point where I thought, my heart can’t take it anymore. I don’t deserve this. I don’t care when people say that I owe him my life because I’m famous now. I don’t owe him nothing.” But that a) isn’t true (not sure you would have made it out video vixen territory without him) and was b) insincere since she also said Kardashian was a homewrecker. But the bald beauty got her revenge on Kim K. when she not only shacked up with Kardashian-ex Reggie Bush, but also scored another hip-hop heavyweight in Wiz Khalifa.


Britney Spears/Kevin Federline/Shar Jackson

Get your eye rolls out of the way now. I know, these three are useless individuals, but their story is, admittedly, very entertaining. So Kevin Federline and Shar Jackson had been a serious item for years (having two children together, including son Kaleb in 2004). And then oops she did that. Spears trotted in and suddenly K-Fed had enough of Jackson (who was pregnant with Kaleb at the time) and started getting with the pop star. Obviously that didn’t go over so well with Jackson, but there was little she could do. By 2004, Kevin became Mr. Britney Spears and enjoyed that sugar mama relationship until November 2006 when the not-so-happy couple divorced. It’s been nothing but pudgy, unsuccessful tears for those three ever since.


Brandi Glanville/Eddie Cibrian/Leanna Rimes

OK maybe we’re lowering our standards given that we’re now including the crazy biznatches on the Real Housewives, but this one is too good to overlook. So Eddie Cibrian (whose personal life has been 10 times more interesting than any of the crap he’s starred in, ever) was married to Brandi Glanville (whose I-don’t-give-a-F attitude really should land her a spot alongside Phaedra and NeNe). Then Cibrian took a gig alongside country crooner LeAnn Rimes in the Lifetime movie Northern Lights. And just like those so-bad-it’s-good Lifetime flicks, drama soon ensued. Rumors of a little knockin’ da boots action on-set soon leaked out, but Glanville stuck by her man … at least for a little while. As soon as Rimes’ divorce was finalized (oh, did we forget to mention she was married too!), Cibrian ran to get that younger woman booty.

Cris Judd/Jennifer Lopez/Ben Affleck

J-Lo, we heart you (and your A$$), but, girl, your love life is a hotness. While it would have been fun to make a chart plotting out Lopez’s many romances or to do some sort of six degrees of separation between all her super hot exs (except for you, P. Diddy), we decided instead to focus on the wonderful Cris Judd-Ben Affleck love-triangle. Hubbies/wives have you learned nothing yet? Beware if your significant other is filming a movie with a ridiculously hot piece of Hollywood tail since there’s about a 50 percent chance you’ll soon be flying solo. While there is some speculation to this love triangle, one thing is certain: Lopez was married to dancer Cris Judd for less than one year before the two split and she found love (at least for a little while) in the arms of Gigli costar Ben Affleck. Before her divorce to Judd was finalized, she was already sporting a marriage proposal from that Hot slice of hot heaven from Boston (excuse us while we cool down for a second). Admittedly an upgrade, but still an eyebrow raising case of musical mattresses.


Natalie Nunn/Wiz Khalifa/Amber Rose

As if appearing on our list once already wasn’t enough, Amber Rose is one of two repeat offenders on the list. Though this love triangle may not have had as much drama as some of our previous entries, it is still worthy of some shameful recognition. Natalie was none too pleased (see what we did there) when she found out that her former flame, Wiz Khalifa, was shacking up with Rose. So, needless to say, that meant she had to pop off at the mouth as quickly and loudly as possible. But given that she’s Natalie Nunn and Wiz had already found some new booty to tap, all that shouting and hollering was really for nothing.

Rachel Worth /

Elin Nordegren/Tiger Woods/Everyone Else (But in this case Rachel Uchitel)

We all know the story, so let’s get to the analysis. Admittedly, this wasn’t really a love triangle. Tiger Woods banged so many women and disrespected his model wife Elin Nordegren to such a ridiculous extent that there really is no name for his actions … so for the sake of simplicity we just went with love triangle. We can all at least take solace in the fact that Nodegren gave it her best effort to beat the bloody hell out of her then-hubby with the help of a golf club. Then she got herself a divorce and a big, fat prize for putting up with Woods’ philandering. While Tiger’s hoes got their 15 minutes of fame during that entire saga, they’ve all largely fallen off the face of the earth with the exception of Uchitel who has continued to pop up in headlines every so often.

Hilary Duff/Aaron Carter/Lindsay Lohan

We’re taking it to the younger set with this particular entry. At the ripe old age of 14 teen idols Hilary Duff and Aaron Carter were happily in … infatuation. They made goo goo eyes at each other and engaged in some awkward teen smooching. This pairing was more cute than illicit, but that didn’t stop drama from rearing its ugly head. Carter was far from a one-woman man and the Duff-ster wasn’t enough to satisfy those raging hormones. So here came Lindsay Lohan to the rescue. When it was revealed that Carter had cheated on his girlfriend with LiLo, Duff hightailed it out of here. And that was probably a good thing. Of everyone involved, Duff, hands down, has had the least awful life. She must look in the mirror each day and thank her lucky stars she didn’t end up with the has-been and that her life hasn’t been spent in countless cell blocks.

Eddie Fisher/Elizabeth Taylor/Richard Burton

You knew we couldn’t compile a list of some of Hollywood’s most scandalous love triangles without including Elizabeth Taylor. Her union with Eddie Fisher was doomed from the start. Not only did she steal the singer away from then-wife Debbie Reynolds, but she would also begin a highly-publicized affair with Cleopatra costar Richard Burton while he was still married. Everyone and their mother (including the Vatican) condemned their relationship, but the two ultimately got divorces and were married for more than 10 tumultuous years. After their first divorce, the two reunited for a second go-round. That failed as well.

Judy Eddy/

Nas/Carmen Bryan/Jay-Z

While there have been plenty of conflicts since, many point to the love triangle between Nas, Carmen Bryan and Jay-Z as the root of their intense feud. In the 2001 release “Supa Ugly,” a response to a Nas diss track, Jay-Z revealed that he (and Allen Iverson) had slept with Carmen Bryan, Nas’ girlfriend and the mother of his daughter Destiny. While Bryan ate up the added attention at the time, she definitely got the short end of the stick in the long run. While Jay-Z is now one-half of hip-hop’s royal couple and Nas is happily married to Kelis, Bryan has done … oh yeah, not a whole lot. Hope you enjoyed those groupie days, girl.

Mike Tyson/Robin Givens/Brad Pitt

OK, so we’ll come out and admit that this one probably doesn’t really fall under the love triangle category since it’s not as if Robin Givens and Brad Pitt ended up having this long-standing, torrid affair. But when we heard the news of Mike Tyson catching his then-wife and hottie Pitt in bed together, we just knew we had to give them some recognition.

Heather Locklear/Richie Sambora/Denise Richards

Straight outta Melrose Place we have one of Hollywood’s most tawdry love triangles. Heather Locklear and Richie Sambora had the grave misfortune of crossing paths with stunner Denis Richards. When Richards marriage to actor and resident hotmess Charlie Sheen came to a screeching halt, she found comfort in the arms of Locklear … and soon her husband. Locklear and Sambora’s union came to an end (after 11 years and one daughter) in 2006 and it wasn’t before long that Richards swooped in to stake her claim to Sambora. While the three went after each other for years, this story has a somewhat happy ending. As Richards and Sambora attempted to rekindle their relationship in 2012, Locklear called her former friend to apologize for how ugly things got between them. Awwww, how sweet!

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