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One of the most popular rappers is in legal hot water on a massive scale. Puerto Rican singer Bad Bunny is riding high, with a Spider-Man spinoff movie on the way and a prominent role in an upcoming WWE pay-per-view. But a major lawsuit has come his way. It could put a damper on his otherwise great year.

The “Mia” rapper put something on one of his albums that may have been ill-advised. His vulnerable approach to lyrics and production may have hit too close to home for someone who used to be a big part of his life. The hit on his bank account might be far more than he ever thought possible.

Bad Bunny is on the wrong end of a massive lawsuit

Rapper Bad Bunny accepts the Best Música Urbana Album for “Un Verano Sin Ti” onstage during the 65th GRAMMY Awards
Bad Bunny at the 2023 GRAMMY Awards | JC Olivera/WireImage

The media has romantically connected just a few women with Bad Bunny over the years. He dated jewelry designer Gabriela Berlingeri for much of the height of his fame, from 2017-22. Lately, the paparazzi have spotted the rapper with reality TV star and entrepreneur Kendall Jenner. Bunny’s troubles stem from his relationship before all that, however.

He dated attorney Carliz De La Cruz from 2011-17, as CNBC reports. She served as his de facto manager during that period. This overlapped with their time together at the University of Puerto Rico. Her voice appears in two Bad Bunny tracks, one from 2016 and another from 2022. That second usage of her breathy recording saying, “Bad Bunny, baby,” likely sealed the rapper’s fate.

They worked together at a grocery store while they dated. But these days, De La Cruz is an attorney with Eldarondo & López-Brass Law Firm in Guaynabo. And she’s seeking $40 million in damages for the usage of her recognizable voice in her former boyfriend’s immensely successful songs.

Bunny isn’t alone in courting controversy that spilled over to the courtroom. Here are five of the most famous copyright lawsuits in music history, according to the BBC:

  • Robin Thicke & Pharrell Williams vs. Marvin Gaye: Williams and Thicke sampled the late Gaye on their massive hit “Blurred Lines.” They were forced to pay a $5 million fine and surrender 50% of past and future profits generated by the song.
  • John Fogerty vs. John Fogerty: Fogerty had the odd experience of being sued for stealing from himself. He demonstrated how his unique guitar-playing style works, and the jury agreed. You can’t copyright a musical style.
  • The Hollies vs. Radiohead: Radiohead’s first major hit, “Creep,” sampled The Hollies.  Albert Hammond and Mike Hazlewood of The Hollies now share writing credits on the creepy single, as well as half the profits.
  • Vanilla Ice vs. Queen & David Bowie: Sampling was a touchy issue as hip-hop emerged as a pop cultural force. One of the biggest tests of sampling was “Ice Ice Baby” liberally pulling from the Queen and Bowie collaboration “Under Pressure.” The case was settled out of court for an undisclosed sum and songwriting credits for members of Queen.
  • 2 Live Crew vs. The Estate of Roy Orbison: The controversial hip-hop group lifted much of Orbison’s song “Oh, Pretty Woman” and made the lyrics offensive. The case made it to the Supreme Court, which ruled the song a parody protected by law.
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Bunny should be more than familiar with how rights work on hit singles. He got his first big boost outside of Puerto Rico by appearing on other people’s tracks. Having Missy Elliott on one of his own tracks means she gets a big chunk of the profits from the song.

But $40 million is a huge overshoot. Bunny’s a massively successful star, sure. Most settlements are less than $10 million in damages, though, so he can sleep better at night.

Rolling Stone reports that there may be some undisclosed sums that are much higher than we’ll ever know, but $40 million is still way beyond the high end. De La Cruz is likely putting that number out there as a way to angle for a sizable — but much smaller — out of court settlement.

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