It may only take two to tango, but it takes three to make some juicy gossip. The latest celebrity love triangle drama between Sabrina Carpenter, Shawn Mendes, and Camila Cabello has reignited our fascination with Hollywood’s messiest relationship drama. And this isn’t the first time we’ve seen sparks fly in unexpected directions, leading to some unforgettable moments.
From the whirlwind drama between Selena Gomez, Justin Bieber, and Hailey Baldwin, to the infamous scandal involving Brad Pitt, Jennifer Aniston, and Angelina Jolie, Hollywood has served up more than its fair share of complicated love stories.
Let’s dive into some of the most iconic celebrity love triangles that have had us hooked over the years.
The Most Iconic Celebrity Love Triangles
Sabrina Carpenter, Shawn Mendes, and Camila Cabello
In the world of pop music, this love triangle has everyone talking right now. Shawn Mendes and Camila Cabello were the it couple from 2019 to 2021, and their split seemed amicable. Fast forward to 2023, Mendes and Carpenter sparked romance rumours, right around the time Mendes was seen rekindling things with Cabello at Coachella. Carpenter, who was already a part of a love triangle with Olivia Rodrigo and Joshua Bassett, seemingly addressed the situation through her music, hinting at a rivalry with Cabello. Lyrics like “You’ll just have to taste me when he’s kissin’ you” from Carpenter’s her latest hit song “Taste” left fans wondering if the pop star drama was far from over.
Justin Timberlake, Britney Spears, and Christina Aguilera
In the early 2000s, the pop music scene was dominated by Britney, Justin, and Christina, who all got their start on The Mickey Mouse Club. While Britney and Justin’s relationship was the stuff of teen dreams, rumours of a love triangle involving Christina kept the gossip mills churning. Though much of the speculation was fuelled by fans and the media, the drama between these pop icons was undeniable.
Brad Pitt, Jennifer Aniston, and Angelina Jolie
Arguably the most famous love triangle of the 2000s, the Brad-Jen-Angelina saga dominated headlines for years. Brad Pitt and Jennifer Aniston were Hollywood’s golden couple until Angelina Jolie entered the picture during the filming of Mr. & Mrs. Smith. Their on-set chemistry led to the end of Brad and Jen’s marriage and the beginning of ‘Brangelina’, which captivated the world.
Jason Sudeikis, Olivia Wilde, and Harry Styles
This Hollywood love triangle became public when Harry Styles joined the cast of Olivia Wilde’s film Don’t Worry Darling. Wilde and Jason Sudeikis had just announced their split, and rumours quickly circulated about Wilde’s new romance with Styles. The drama hit its peak when Sudeikis served Wilde custody papers while she was on stage at CinemaCon. The situation turned messy, with Wilde accusing Sudeikis of trying to publicly humiliate her. However, Wilde and Styles have since split.
John Mayer, Taylor Swift, and Katy Perry
Taylor Swift and Katy Perry’s feud is legendary, with many believing that John Mayer was at the heart of it. Mayer dated Swift in 2009, an affair that ended on a sour note, as captured in Swift’s scathing track “Dear John”. A few years later, Mayer and Perry started dating, which reportedly added tension to an already strained relationship between the two pop stars. While both women have since moved on, the drama left an indelible mark on their careers.
Related: Unpacking the Drama Between Taylor Swift and Katy Perry, A Decade Later
Kylie Jenner, Tyga, and Blac Chyna
This love triangle is as messy as they come. Tyga and Blac Chyna were together from 2011 to 2014 and even had a son. But soon after their split, Tyga and Kylie Jenner became an item — though they only went public after Kylie turned 18 in 2015. The timing was suspicious, and fans couldn’t help but side-eye the whole situation. As if that wasn’t enough, Blac Chyna later got engaged to Kylie’s brother, Rob Kardashian, adding another layer of drama to this already tangled web.
Selena Gomez, Justin Bieber, and Hailey Baldwin
The Selena-Justin-Hailey saga is one of the most well-documented love triangles in pop culture. Selena and Justin’s on-again, off-again relationship captivated fans for years. However, things took a dramatic turn when Justin started dating Hailey Baldwin, whom he would go on to marry just months after his final split from Selena in 2018. The drama didn’t end there, as Selena’s hit song “Lose You to Love Me” was widely interpreted as a reflection on her tumultuous relationship with Bieber, adding another chapter to this never-ending story.
Jay-Z, Beyoncé, and “Becky With the Good Hair”
When Beyoncé dropped Lemonade, the world stood still — not just for the music, but for the bombshell revelation of Jay-Z’s infidelity. In “Sorry”, Beyoncé sings, “He better call Becky with the good hair”, sparking a frenzy as fans speculated who “Becky” could be. Fingers pointed at designer Rachel Roy and singer Rita Ora, though both denied involvement. While the identity of Becky remains a mystery, the scandal solidified Beyoncé and Jay-Z as the power couple who turned pain into art.
Lilly Jay, Ethan Slater, and Ariana Grande
Ariana Grande found herself in a real-life love triangle while filming Wicked. Ethan Slater, Grande’s co-star, was married to his high school sweetheart, Lilly Jay, with whom he had just welcomed a child. Meanwhile, Grande was married to Dalton Gomez, making this more of a love square. When Grande’s divorce was announced in July 2023, it wasn’t long before Slater also filed for divorce, and the two went public with their relationship. Lilly Jay, feeling blindsided, later called out Grande, stating, “She’s not a girl’s girl”, further fuelling the scandal.
Kristen Stewart, Robert Pattinson, and Rupert Sanders
Kristen Stewart and Robert Pattinson were Hollywood’s golden couple, thanks to their onscreen romance in the Twilight saga. However, things took a dark turn when Stewart was caught cheating with her Snow White and the Huntsman director, Rupert Sanders. The scandal led to Sanders’ divorce from his wife, Liberty Ross, and caused a significant rift between Stewart and Pattinson. While they attempted to reconcile, the relationship ultimately couldn’t withstand the betrayal.
Taylor Swift, Joe Jonas, and Camilla Belle
Taylor Swift’s brief romance with Joe Jonas ended with a notorious 27-second phone call, leading to the release of her scathing track “Forever & Always”. Joe quickly moved on with actress Camilla Belle, prompting Swift to pen another biting anthem, “Better Than Revenge”, where she called out the actress for “stealing” her man. Years later, both Jonas and Swift have seemingly buried the hatchet.
Sabrina Carpenter, Joshua Bassett, and Olivia Rodrigo
The “Drivers License” drama had everyone talking in 2021. Olivia Rodrigo’s breakout hit, rumoured to be about her ex Joshua Bassett and his relationship with Sabrina Carpenter, became the soundtrack of heartbreak for an entire generation. While Olivia’s song topped the charts, fans were left speculating about the real-life drama that played out behind the scenes.
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