Brad Pitt, Jennifer Aniston, Angelina Jolie

When we talk about entanglements that get messy, these three will never be missing. The legendary story of how Jennifer Aniston and Brad Pitt were married when Pitt and Jolie met and co-starred on Mr. & Mrs. Smith will never be forgotten by the public. Back then, rumors about Pitt and Jolie’s affair started soon after the filming, and it didn’t take very long for Aniston to hire a divorce attorney soon after. Now free, Pitt was open about his relationship with Jolie— and from there came “Brangelina,” the greatest love team Hollywood has ever seen. The Friends star sure didn’t agree about this. As Aniston moved on, Brangelina became known for their celebrated love story, and the world followed as their family grew.

Kim Kardashian, Kris Humphries, Kanye West

Kanye West and Kim Kardashian are a power couple now, but before they lived happily ever after and raised four kids of their own, a lot of drama has transpired. Apparently, West fell in love with Kardashian when she was still in a relationship with Brooklyn Nets’ power forward Kris Humphries. These occurrences were narrated in West’s song Theraflu in 2012. His lyrics talked about how he admitted to having been smitten by Kardashian when she was still tied to someone else. He even said, “Lucky, I ain’t had Jay drop him from the team.” He meant the Brooklyn Nets, which was owned by Jay-Z, a good friend of West’s. In the end, he has made an investment by turning his love story into a great track.

Rihanna, Jennifer Lopez, Drake

Singers Rihanna and Drake have gained popularity together not only because of recording songs together but also because of their relationship with each other. Rihanna was very open about not wanting to commit to Drake, who was quite smitten by her. It all began to turn sour after Jennifer Lopez once shared a picture on Instagram featuring her and Drake cuddling next to each other. The photo was quite intimate, and when Rihanna saw this, she immediately unfollowed both singers. Though the picture had no caption, many speculate that it was posted to make Rihanna jealous. The degree of drama escalates because Rihanna and J-Lo apparently are good friends. They only spoke of each other in good light, and they gave each other great and thoughtful presents too. After the fiasco, who knows if they still remained friends?

Britney Spears, Kevin Federline, Shar Jackson

We all know that the father of pop star Britney Spears’ first child is Kevin Federline. But what we don’t know is that apparently, Federline was attached to someone when he ran off with Spears. In 2004, Federline was engaged to Shar Jackson from Moesha. She was not only his fiancée, but she was also pregnant when he left her. A while after being with Federline, Spears got pregnant with his baby as well. The degree of publicity in Spears’ relationship with Federline was massive, and everything they did was always in the headlines. Jackson, on the other hand, moved on and created RelationLips, her own cosmetic line with the debut lip gloss called He Cheated as her front line product.

Selena Gomez, Taylor Swift, Taylor Lautner

Singer and songwriter Taylor Swift has a long list of ex-lovers, and she has all kept anecdotes of her relationships in her songs. Apart from the men in her life, she also has an extensive list of celebrity best friends that she has fallen in and out of touch with. One crossroad of these lists is when she and one of her BFFs, singer Selena Gomez, both dated the same guy– actor Taylor Lautner. Apparently, this does not bother Swift as she told Vanity Fair in one interview that she and her group of friends have a bond that goes beyond guys that they dated. Even though at some point some of them may have had the same electricity for the same men, it should not be a reason for a feud to take place.

John Mayer, Taylor Swift, Katy Perry

Pop stars Taylor Swift and Katy Perry have been very vocal and open about their hate for each other. They have featured each other in their own music and music videos. It has been a long time since the feud started, and the official statement of both ladies was that they fought over backup dancers at some point. However, fans hypothesize that the fact that both girls dated singer John Mayer may have also added more insult to injury. Swift and Mayer were together in 2009, and she made a song about their relationship called Dear John. It was not a happy song. Meanwhile, Perry and Mayer got together in 2012 too. It’s not a long shot, but Mayer might get credit for the bad blood between the two female artists.

Alex Rodriguez, Kate Hudson, Cameron Diaz

Kate Hudson and Alex Rodriguez saw each other for a while before, but when they split up, Rodriguez’s new love life was not good news to Hudson. Rumors of Cameron Diaz leaving Rodriguez’s place a few months after their split with big bags surfaced, and this did not sit well with the ex-lover. According to Us Weekly, they credit a trusted source that said that Hudson was “pissed” with Diaz because of the news she heard. It comes off as a surprise that Hudson was taking the new relationship personally, after all these months following their breakup. The media and all the paparazzi were all abuzz on what would happen next between the two ladies, and they were on their toes for the next couple of weeks after that.

Jay-Z, Beyoncé, “Becky”

Power couple Jay-Z and Beyonce have been hailed as one of the most influential couples in Hollywood to date. When Beyonce released her emotional album Lemonade, however, the whole world was surprised that she confirmed her husband had been cheating on her with a girl which she named ”Becky” in her songs. Like any good fanbase, the Beyhive tried their best to determine who this girl was. Some speculated that it was designer Rachel Roy, and some said it could have been singer Rita Ora, but both denied having anything to do with the entanglement. It’s a good thing for Beyonce, though, because she made an investment of turning her emotions into one big chart-topping album that will make her a huge fortune.

Cazzie David, Pete Davidson, Ariana Grande

Cazzie David and Pete Davidson were together for two years. At the same time, Ariana Grande and Mac Miller were also together for two years. As David’s and Davidson’s relationship was reaching its end, Grande’s and Miller’s were also close to calling it quits in 2018. Both relationships seemed to have reached its end at the same time – this also happened around the time frame when Grande and Davidson started seeing each other. Of course, it would follow that the public would think that their breakup from their former partners was due to them being together. It didn’t help that just a short while after, they announced that they were engaged already after only a few months. They didn’t go through with it and broke up four months later, though, so no need for a lawyer.

Kylie Jenner, Tyga, Blac Chyna

Blac Chyna and Tyga were a couple for years before they got entangled with the Kardashian-Jenner clan. The two started dating in 2011 and broke up in 2014, but not before having a son together. Rumors about Tyga and Kylie Jenner’s relationship with each other, though, started when Tyga performed for Kylie’s sister Kendall’s 16th birthday party in 2011 as well. It was when Kylie turned 18 in 2015, however, that the two claimed to be together officially. Some say that Tyga had been dating the underaged Kylie before this time, but they never really confirmed. Some are even bolder to say that they were together before Tyga broke up with Chyna. We never really know where credit is due with all these timelines.