When Celebs Mixed Business With Pleasure (And It Totally Backfired)

Mixing romance with work usually sounds like a movie plot, but in Hollywood, it plays out in real life—and not always in the best way. Some celebs tried to balance love and money, but it got messy fast. These moments turned into real-life PR nightmares.

Amber Heard

Starring alongside Johnny Depp in “The Rum Diary” set off a real-life connection that turned into one of Hollywood’s ugliest public feuds. Amber Heard’s marriage to him ended in 2016, but the courtroom drama dragged on until 2022. The defamation trial even aired live on TV and had its own three-part Netflix documentary.

Guy Ritchie

Guy Richie’s union to Madonna brought the 2002 box office bomb “Swept Away.” Despite his previous success with “Snatch,” critics called this film a disaster. It earned under $600,000 in the U.S. and got a 5% score on Rotten Tomatoes. The marriage ended six years later, with a pricey settlement.

Nicole Kidman

When Nicole Kidman spent over a year filming “Eyes Wide Shut” with Tom Cruise, it tested acting limits but also strained their relationship. The shoot reportedly took more than 400 days, with intense emotional scenes. They announced their divorce soon after filming wrapped. The Oscar winner later admitted she wasn’t prepared for how fast things ended.

Kristen Stewart

Kristen Stewart’s involvement with her director, Rupert Sanders, during the “Snow White and the Huntsman” shoot led to major fallout. Photos of them together surfaced in 2012, and Kristen issued a public apology to then-boyfriend Robert Pattinson. She wasn’t brought back for the sequel, and Rupert’s marriage collapsed soon after the scandal broke.

Angelina Jolie

Filming “Mr. & Mrs. Smith” with Angelina Jolie sparked headlines worldwide because Brad Pitt was still married to Jennifer Aniston when the movie premiered in 2005. Although the film was a hit, pulling in $487 million globally, their romance eventually collapsed in 2016. Custody battles and leaked court docs have haunted Angelina ever since.

Liam Hemsworth

Liam Hemsworth fell for Miley Cyrus while filming “The Last Song” in 2009. Their years-long rollercoaster relationship ended in a short-lived marriage from 2018 to 2020. Following the breakup, Miley released “Flowers,” which fans widely viewed as a response to their relationship. Liam’s career shifted quietly afterward, as headlines focused more on the drama than his work.

Kanye West

Kanye mixed love and business when Kim first appeared in music videos and even launched fashion lines. However, things fell apart after his 2020 presidential bid and a series of public meltdowns. In 2021, Kim Kardashian filed for divorce, and Kanye lost multiple deals, including partnerships with Adidas and Balenciaga.

Nick Lachey

“Newlyweds: Nick and Jessica” put Nick Lachey’s relationship with Jessica Simpson under a microscope from 2003 to 2005. While the MTV show boosted both their profiles, it also highlighted their incompatibilities. The pair divorced shortly after, and Nick later said the cameras made it impossible to have normal couple arguments without an audience.

Britney Spears

Kevin Federline shot to fame when he married Britney Spears in 2004 and starred in their reality show “Chaotic.” The show received terrible reviews, and the “Lucky” songstress later said she regretted doing it. They divorced in 2006, and Kevin was awarded custody of their two sons.

Sean Penn

“Shanghai Surprise” in 1986 saw Sean Penn team up with Madonna. It tanked at the box office, and critics hated it. Their relationship, already full of volatility, got worse under the spotlight. Rumors of on-set fights and legal issues followed. They divorced just three years later, and the movie became a running Hollywood joke.

Ben Affleck

Ben Affleck teamed up with Jennifer Lopez for the 2003 romantic comedy “Gigli,” which became one of the biggest box office failures of the decade. It earned just $7 million on a $75 million budget. Their high-profile relationship crumbled shortly after, and Ben admitted years later that the media attention was overwhelming.

Justin Theroux

Jennifer Aniston met Justin Theroux while working on “Wanderlust.” The film flopped, grossing under $25 million worldwide, and failed to give either star a box office boost. Their relationship, although promising, faced the pressures of long-distance living and constant media scrutiny. They married in 2015 and quietly split two years later, citing differences in lifestyle and priorities.

Jada Pinkett Smith

With her Facebook show “Red Table Talk,” Jada Pinkett Smith talked openly about her marriage to Will Smith, including a romantic entanglement with August Alsina. The 2020 episode reached tens of millions of views. It sparked memes, debates, and ultimately contributed to the 2022 Oscars incident, when Will Smith slapped Chris Rock during the live broadcast.

Grimes

Elon Musk and Grimes grabbed headlines starting in 2018 for everything from baby names to AI art performances. Their personal life blended into their creative projects, which confused even their fans. By 2021, the couple said they were “semi-separated.” She later filed a lawsuit in 2023 over parental rights related to their children.

Cash Warren

Cash Warren began his career as a production assistant on “Fantastic Four,” where he met Jessica Alba. They eventually married in 2008, but Alba admitted in interviews that juggling motherhood and business with Warren’s projects at The Honest Company led to burnout. Their personal life took a hit during the early years of their partnership.