Timbaland just sued the 2 men who ran his money for $15 million. He says one took an extra $500,000 on each of two $5 million Verzuz payments, while the other paid himself and lawyers nearly $900,000 in 5 months and let his mortgage go unpaid for 12. He found out when a foreclosure notice showed up at his house. In the video below, Timbaland explains why he doesn't really think about money. He'd "rather have a rich spirit." He's the producer behind hits for Missy Elliott, Aaliyah, Justin Timberlake and Jay-Z. In 2016 he hired manager Gary Marella and business manager Bruce Seckendorf. He was already dealing with misconduct claims against the people who handled his money before them. In 2019 he sold his catalog to Hipgnosis. The lawsuit says Marella took $775,000 more than his 10% commission. In 2020 he launched Verzuz with Swizz Beatz. The suit says that's where the extra $500,000, twice, came from. Meanwhile Seckendorf's firm missed federal tax payments. Millions in penalties and interest. The 65-page complaint was filed Friday in Los Angeles. Fraud, civil theft, breach of fiduciary duty. "The foreclosure was not caused simply because Plaintiffs had no money." Marella denies all of it. He says Timbaland knew the commission was 15%, that they brought in about $75 million together in 9 years, and that Timbaland is blaming someone else for his own spending, "again." He said he'd rather have a rich spirit than money. He says the men holding his money felt the opposite. Did Timbaland get robbed by the people he trusted, or is he blaming them for his own spending?

Drake signed a $400 million deal with Universal Music. Two years later, a Universal label released a song calling him a "certified pedophile," and it did 96 million streams in 7 days, 5 Grammys and a Super Bowl show for 133 million people. He sued his own label, saying it gave Spotify a 30% discount to push the song. A judge threw the case out. On December 4, he gets one more shot. In the video below, Kendrick Lamar stands on the Super Bowl stage and says he'd play their favorite song, "but you know they love to sue." Insiders called Drake's deal "LeBron-sized." Variety put it near $400 million, with his music bringing Universal around $50 million a year. Kendrick is on Interscope. Interscope belongs to Universal too. "Not Like Us" dropped in May 2024. 12.8 million Spotify streams in a single day, a rap record. Over 1 billion streams. 53 weeks on the Billboard Hot 100, the longest run ever for a rap song. The same week, Drake's own diss "Family Matters" debuted at number 7 with 38 million streams. Kendrick's debuted at number 1 with 70.9 million. Almost double. Drake says the accusation in the song is false. His filings claimed bots, paid radio play, a 30% cheaper Spotify license and even payments to Apple so Siri would steer users to the song. Universal denies all of it. Universal called the lawsuit an attack on creative freedom that never should have been filed. In October 2025 a federal judge agreed. She ruled the lyrics were trash talk from a rap battle, not facts anyone would take literally. Drake appealed. He still puts out his music through Universal. Universal paid Drake $400 million to make hits. It also got paid for the biggest hit ever made against him. Was Universal just doing business, or did Drake's own label cash in on destroying him?

Shakira paid Spain an $8 million fine and took a 3-year suspended sentence to end a $15 million tax case, after prosecutors asked for 8 years in prison. Their proof she lived there was Gerard Piqué, the boyfriend she later wrote a breakup diss about. Now a Spanish court has ordered the tax office to give her back $64 million. 8 times the fine she paid, because Spain came up 20 days short. In the video below, Shakira explains why women have spent too long hiding their pain, even in front of their own kids. She met Piqué filming the 2010 World Cup song. They had two sons and lived in Barcelona. Spain said she owed tax for 2012 to 2014. Her side said she was touring the world and wasn't a resident. On top of prison, prosecutors asked for a $26 million fine. The tax office went through her social media posts to count the days she spent in the country. In June 2022 she and Piqué split. Piqué had paid his own tax fraud fine back in 2019. In November 2023, on the first day of her trial, she took the deal. "I need to move past the stress and emotional toll of the last several years." She had already moved to Miami with her boys. Then came the 2011 case. Spain had charged her more than $64 million in tax and penalties for that year, again pointing to her relationship with Piqué. In May a national court ruled the tax office could only prove 163 days in Spain. The legal line is 183. Spain has to pay it all back with interest, unless it wins an appeal. "There was never any fraud," she said. This fall she's back in Spain. For a concert residency in Madrid. Spain used her love life as evidence. Now that evidence could cost Spain $64 million. Did Shakira beat the tax office, or did she pay for the years they could prove?

Michael Oher was the homeless kid in The Blind Side, a $300 million hit that won Sandra Bullock an Oscar. In 2023, he says he found out the family from the movie never adopted him. They had made themselves his conservators instead. For almost 20 years they had legal control over his deals. In the video below, Good Morning America visits the Tuohys in 2009 and tells the country that Michael was "eventually adopted by the family." Oher was 18 when he signed the papers in 2004. He says he was told it was part of the adoption. Two years later the Tuohys negotiated the movie deal. His lawsuit says Sean, Leigh Anne and their two kids were each promised $225,000 plus 2.5% of the profits. Sean Tuohy first said they hadn't made any money from the film. Then he said everyone, Michael included, got about $14,000. Their own accounting later showed the family received more than $432,000 from the studios, and paid Oher $138,311 in ten checks over 16 years. Oher's lawyers put it simply: "Without Mr. Oher, there would be no movie." And one detail tells you how it looked from the other side. The Tuohys' lawyer said they never needed his money, because Sean Tuohy sold his company for $220 million. In 2023 a judge ended the conservatorship. She said she was disturbed he had ever been put in one. The Tuohys deny taking advantage of him and called his lawsuit ludicrous. The movie made them America's favorite family. The paperwork made them his managers. Was it love that got complicated, or a business that called itself a family?

Prince signed the biggest record deal in history, $100 million from Warner Bros. Within three years he was walking into award shows with "SLAVE" written on his face. The deal beat Michael Jackson's and Madonna's. He still didn't own the recordings of a single song he'd made. In the video below, Prince does the math on a talk show. Sell a million records on your own, keep about $10 million. By the end, Mariah Carey's $20 million deal sounds like a bad one. Warner signed him at 18. By 1992 he was one of the biggest stars on the planet. The new contract covered six albums. $10 million per album, a vice president title at Warner, a joint label for his Paisley Park. His managers announced it as a $100 million deal. Michael Jackson's Sony deal a year earlier was about $50 million. Here's the catch. The $10 million only came if the album before it sold enough. And Warner owned his master recordings. Forever. Prince wanted to release music as fast as he made it. Warner worried the market couldn't take that much Prince. In 1993 he dropped his name and became a symbol. Then he wrote one word on his cheek. At the 1995 BRIT Awards he won Best International Male and said fewer than 20 words. "In concert, perfectly free. On record: slave." Warner cut the distribution deal for his Paisley Park label. It went out of business. He got out in 1996 and released a three-disc album on another label. He called it Emancipation. That year he told Rolling Stone: "If you don't own your masters, your master owns you." Warner finally gave him his masters in 2014. 22 years after the $100 million headline. $100 million: the headline. $10 million: per album, if the last one sold. 0: master recordings he owned. Was Prince a slave to Warner Bros., or a superstar who signed for $100 million and hated the fine print?

Leonardo DiCaprio got Marlon Brando's Oscar and a $3.2 million Picasso from the men who paid for The Wolf of Wall Street. US prosecutors say the money came out of $4.5 billion stolen from Malaysia. The man behind it is still on the run. Leo had to hand everything back to the government. In the video below, DiCaprio wins a Golden Globe for the movie and thanks its producers, "Joey, Riza," for "taking a risk on this movie." Riza is Riza Aziz, stepson of Malaysia's prime minister at the time. His company, Red Granite, made the film. His close friend Jho Low was the money man. Prosecutors say Low looted 1MDB, a Malaysian state fund, and more than $100 million of it went into Red Granite's movies. Low was thanked in the film's credits. For Leo's 38th birthday they gave him Brando's Oscar for On the Waterfront. It cost about $600,000. Then came a Picasso, bought with $3.2 million prosecutors say was taken from the fund. The note said: "Happy belated Birthday! This gift is for you." And one detail tells you how far it went. Court papers say Leo gambled with Low and the producers at the Venetian in Las Vegas in 2012. $1.15 million came out of Low's casino account in a single day. In 2016 the US government went after the movie's profits. Leo gave back the Oscar, the Picasso and a Basquiat. He was never accused of wrongdoing. Red Granite paid $60 million to settle and admitted nothing. Last December the former prime minister got 15 more years in prison. Jho Low has never been caught. Leo played a man who stole from strangers and bought everyone around him. Prosecutors say the movie itself was paid for the same way. Did DiCaprio really not know where the money came from, or did nobody in Hollywood want to ask?

Lil Wayne says Birdman sat on $10 million of his money and 49% of the label that signed Drake and Nicki Minaj. So he sued the man he called his father for $51 million. In the video below, the two of them sit side by side on Rap City in 2007. Then Tampa, 2025, when Birdman tries to give a speech on stage. Wayne joined Cash Money in 1997. In 2006 he and Birdman put out a joint album. It was called Like Father, Like Son. The single was "Stuntin' Like My Daddy." Wayne started his own label inside Cash Money, Young Money. It signed Drake. It signed Nicki Minaj. Then his album Tha Carter V got stuck. In December 2014 he tweeted: "I am a prisoner and so is my creativity." And: "I want off this label and nothing to do with these people but unfortunately it ain't that easy." A month later he sued Cash Money and Birdman for $51 million. His side said Birdman owed him an $8 million advance for the album and $2 million more once it was done. He said he never got the 49% of Young Money he was due. The label had registered Young Money under Cash Money. So, he said, he never saw an accounting of what Drake made for it. It took three and a half years. In June 2018 they settled. The terms are secret. Reports said more than $10 million. Hours later, a photo showed the two of them in the studio together. Tha Carter V finally came out that September. Then came Tampa. February 2025, the Hot Boys reunion. Birdman was talking to the crowd. Wayne cut him off mid-speech: "Alright, let's go, let's go, let's go." Like Father, Like Son, the album said. The son needed a $51 million lawsuit to get paid. Was Birdman the father who made Lil Wayne, or the boss who kept his money?

The Emperor's New Groove made Disney $169,000,000 in theaters, and David Spade says they paid him $75,000 to voice Kuzco. Then Shrek came out, and he says everyone in it got $5,000,000. And that was before the movie sold millions of tapes. In the video below, Spade tells Dana Carvey and Denis Leary what Disney told him instead of a raise. He was cast in 1997, when the film was still a big musical called Kingdom of the Sun. Disney tore it up halfway through, stopped production for six months and rebuilt the whole thing as a comedy around his character. He says the job took about three years. "I was the last guy to do a Disney movie where they said it was an honor, and that's why I didn't get a lot of money." Carvey guessed $18,000. Spade corrected him: "No, I got $75,000, which sounds like a lot. It was a lot." Then DreamWorks released Shrek, and he saw what its stars were paid. "Everyone got 5 million bucks." The Emperor's New Groove became the best-selling home video in America in 2001. About 6 million VHS tapes in its first year, and reportedly twice that on DVD. Disney kept going. A sequel. A TV show. In the TV show, Kuzco had a new voice. In 2023 he joked that the movie "did not pay for the house we are recording in." Leary said Disney ripped him off. Spade didn't argue. "They rat f***ed me." $169 million: the box office. 6 million tapes: year one. $75,000: Kuzco. Was it an honor to be in a Disney movie, or just the cheapest way to pay the star?

Spotify paid Prince Harry and Meghan Markle a reported $20 million. They made 12 episodes. Then Spotify's own podcast boss called them "f***ing grifters." In the video below, Harry tells Oprah his own family cut him off financially, and you see the Netflix show that came right after. In early 2020 they stepped back as working royals and moved to California. The palace money stopped. "I've got all my mom left me, and without that we would not be able to do this," Harry said. Then the deals came. Netflix, a reported $100 million for five years. Spotify, a reported $20 million for podcasts. Spotify got one show. Meghan's Archetypes ran for 12 episodes. That's about $1.7 million an episode. In June 2023 Spotify and the couple "mutually agreed to part ways." A few days later Bill Simmons, Spotify's head of podcast innovation and monetization, went on his own show. "The f***ing grifters. That's the podcast we should have launched with them." He said he had been "embarrassed" to share the platform with Harry. When the Netflix deal ran out in 2025, Netflix renewed it, but smaller. Now it only gets the first look at their ideas, and it can say no. They left the palace to make their own money. One company paid them $1.7 million an episode, then called them grifters on the way out. Were they grifters, or did Spotify just pay for a famous name and expect a show?

Kevin Costner's wife asked for $248,000 a month in child support. The judge gave her $63,209, and ordered her to pay $14,237 of his lawyer's bill. In the video below, Costner stops outside the courthouse and tells a reporter what it feels like to be there. They were married for 18 years and have three kids together. It was his second divorce. The first, in 1994, reportedly cost him $80 million. So before he married Christine, he made sure there was a prenup. "The last thing I wanted was to not be able to come home to my home with my children," he told the court. One line in it mattered more than the rest. If they ever split, she would move out of his house within 30 days. In May 2023 she filed for divorce. She didn't move out. Her lawyers asked for $248,000 a month for the kids. Costner offered $51,000. A judge first set it at $129,755. Then came the trial. When her side went through the family's expenses, Costner stopped them with one question: "Is this after the day she left me?" He said his biggest fear was being ordered to pay so much that he would "run out of cash." The judge cut it to $63,209 a month. Then he made her pay $14,237 of Costner's legal fees, over the fight about whether she had understood the prenup she signed. She was ordered out of the house by July 31. Less than three weeks after the ruling, they settled. Outside court he said it felt "so bad" and that he still loves her. Inside, his lawyers made her pay for their time. Was $248,000 a month fair for three kids, or was she trying to get around the deal she signed?