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Macaulay Culkin got $110,000 for “Home Alone.” The movie made $476 million. Two years later, he reportedly got $4.5 million for the sequel, plus a cut of every Talkboy sold. In the video below, Hot Ones host Sean Evans asks him why “Home Alone 2” is better than the first. His answer: “I got paid more.” He was nine when they shot the first film. It was a modestly budgeted Christmas comedy, and nobody expected a global hit. For the sequel, he became the highest-paid child actor in Hollywood at the time, reportedly. That is about 40 times what he got for the first film. The money did not stop there. “I think I owned 5% of the net,” he says. He also had 15% of the merchandising. That meant the Talkboy, the little recorder Kevin uses in the movie. “If you buy a Talkboy, I’m like, ‘Yeah, I’ll take 15% of that.’” The sequel made over $350 million on a budget of about $28 million. The case for the studio: it hired a nine-year-old with almost no track record for a movie nobody expected to work. $110,000 was a normal child-actor fee. The big money came only after he proved he could carry a franchise. So did Culkin get underpaid for the first film, or did the second one make up for it?

Snoop Dogg says his music hit a billion streams on Spotify. His check wasn’t even $45,000. That’s about $45 for every million plays. In the video below, he tells the Business Untitled podcast how he found out. His publisher sent him the Spotify numbers. A billion streams. He asked for one thing: “Break that down. How much money is that?” “That shit wasn’t even $45,000.” Then he says it again, slower: “Crazy.” This is one of the most famous rappers alive. 30 years of hits. And a billion plays paid less than a mid-level salary. So he tried something else. With his son, he started selling music directly to fans through NFTs. His split was simple: he takes 60% for putting the song out, the artist takes 40%. “That may sound like a lot, but you just made $100,000.” And every time the song is resold, the original artist gets 10%. “Without Sony, Apple, all these taking percentages.” His point is transparency. Every sale shows up in the artist’s wallet. No waiting for a statement from a label. His closing line: “You got to get a billion streams to get 45,000. You sell a hundred, and if you’re selling it for $10, you do the math.” The case for Spotify: it doesn’t pay artists directly. It pays labels and publishers, and they pay artists under their own contracts. Snoop’s $45,000 may only be one slice of what that billion streams earned. So who really got Snoop’s money: Spotify, the labels, or the contracts he signed?

Harrison Ford was paid about $10,000 to play Han Solo. Star Wars made over $300 million in its first release. Alec Guinness took a cut of the box office instead. Over his lifetime, it reportedly made him about $100 million. In the video below, Ford tells Good Morning America how he got the part, and what he said when he heard the offer. He wasn’t even auditioning. A producer friend got him to read lines with the actors trying out for Luke and Leia. He thought he was just doing George Lucas a favor. When it was over, they asked if he wanted to play Han Solo. His first question: “How much?” They said $1,000 a week. “And I said no.” Then he laughs. “But I did. I did it for $1,000 a week for the first one.” That came to about $10,000 for the whole film, reportedly. Alec Guinness, who played Obi-Wan, made a different deal: a $150,000 salary plus 2.25% of the gross. Star Wars became the highest-grossing movie in history at the time. Asked if his pay went up for the sequels, Ford smiles: “A little bit.” 38 years later, for The Force Awakens, he was reportedly offered up to $25 million upfront. The case for the studio: in 1976, Ford was a supporting actor with almost no leading roles. Nobody knew if a space movie would work, and $1,000 a week was a normal rate for an unknown. Guinness was already an Oscar winner, so he had the leverage to ask for a percentage. So was $1,000 a week fair for an unknown actor, or did Star Wars owe Han Solo more?

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Matthew McConaughey turned down $14.5 million to make one more romantic comedy. A few years later, he won an Oscar for a movie made on $4.9 million. In the video below, he tells Steven Bartlett on The Diary of a CEO how the offer kept going up. In the 2000s, he was Hollywood’s go-to rom-com guy. The movies paid well, and the scripts kept coming. But he wanted dramas, and nobody would cast him in one. So he moved to his ranch in Texas and told his agent: no more rom-coms. His wife Camila was pregnant with their first child. For months, nothing came. He says he thought about becoming a teacher or going back to law school. Then an offer came in. $8 million. He said no. They came back with $12 million. No. Then $14.5 million. “Let me read that again.” He says it was the same script he had already turned down at $8 million. “But it was better written.” He still said no. His brothers asked him: “What is your major malfunction, little brother?” He believes that one “no” told Hollywood he was not bluffing. “He’s not for rent.” About 20 months after he walked away, the offers he wanted started coming in. Mud. Magic Mike. True Detective. Then Dallas Buyers Club. It was shot in 25 days on $4.9 million, and it won him the Oscar for best actor, a goal he says he had written down in 1992. The case for the skeptics: he already had years of rom-com money in the bank. Saying no to $14.5 million is easier when you can afford 20 months without a paycheck. Most people can’t. So was it courage, or a bet only a millionaire could afford to make?

Steve Jobs reportedly put $10 million into Pixar in 1986. Disney paid $7.4 billion for it in 2006. That sale price was 740 times his investment. Ten years before the sale, Jobs explained in an interview why Pixar gave its employees stock instead of contracts. In the video below, he walks through that choice, and the commercials business Pixar walked away from. He met Ed Catmull in 1985. Catmull ran the computer division at Lucasfilm. Catmull had a dream: the first computer-animated feature film. Jobs says he bought into it financially and spiritually. It took 10 years. Toy Story opened in November 1995. A week later, Pixar went public at a valuation of about $1.5 billion, the largest IPO of the year. Pixar also had a commercials unit. Jobs says it won almost every award in the business. It was work for hire. Pixar got paid once and shared none of the upside. His example: if a client sold more Listerine because of a Pixar ad, Pixar earned nothing extra. In 1996, Pixar pulled out. Twenty-five people had been working there. Hollywood keeps talent with contracts, Jobs says. Silicon Valley uses stock options. Pixar chose stock. He also says power flips in a studio like that: “the CEO is actually at the bottom.” The case for contracts: Jobs admits there are good reasons to lock people in for a film. If someone leaves mid-project, the studio is at risk. A contract guarantees the team. Stock only pays off if the company wins. Was Jobs right that stock beats a contract, or did it only work because Toy Story was a hit?

Arnold Schwarzenegger took no salary for Twins. The movie made $216 million. He says it paid him more than $40 million. More than any movie he has ever made, including The Terminator. In the video below, Andy Cohen asks which film earned his biggest paycheck, then starts guessing the number. He has said Universal doubted an action star could carry a comedy. So Schwarzenegger, Danny DeVito and director Ivan Reitman skipped their salaries and took a piece of the back end. The budget was under $20 million. Cohen asks: more than $20 million? “Much more,” Arnold says. More than $40 million? He says it was more than that. A sequel, Triplets, was planned, with Eddie Murphy as the third brother. It never happened after Reitman died in 2022. The case for the studio: it was betting on an action star in a comedy he had never done. Skipping salaries kept the risk low. Nobody expected the film to become his biggest payday. So did Universal protect its budget the smart way, or hand Arnold the best deal of his career?

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In 2019, Scooter Braun bought the label that owned Taylor Swift’s music, in a deal reported at over $300 million. In 2025, she reportedly paid about $360 million to get it back. In the video below, Taylor tells Travis Kelce how it really happened. She signed her first record deal at 15, and says she “never owned my music at all.” That is how most record deals work. The label owns the masters, and the artist doesn’t. She says she started saving money to buy her songs back when she was a teenager. The first time her catalog was sold, she says it “ripped my heart out.” So she started re-recording her albums, because it was the only way she thought she could ever own them. When she began in 2021, she says most of the industry trades called it a bad idea. After the Eras Tour, she decided to approach the current owner, the private equity firm Shamrock Capital. She wanted to buy her music outright, not own 30% of it. She didn’t send lawyers. She sent her mom and her brother. “I would so much rather lead heart first,” she says. This wasn’t about returns. It was her handwritten diary entries, her photography and her music videos. A couple of months after the Super Bowl, her mom called. They had said yes. Taylor says she “very dramatically hit the floor” and started sobbing. At 35, she finally owned everything she wrote as a teenager. The case for the buyers: Braun and Shamrock paid market price for an asset the label legally owned. Taylor signed that contract herself, at a time when the standard deal gave the label the masters. So was it fair that she had to buy her own songs, or is that just how the music business works?

In 1975, Sylvester Stallone was so broke he sold his dog. Then a studio offered him $360,000 for a script he wrote in 3 days. He said no. In the video below, Stallone tells CBS’s Tracy Smith why: “I said, pass. I can’t do it.” He was living in New York with pizza boxes for a mattress. He cleaned the lion cages at the Central Park Zoo. By March 1975 the Rocky script was finished, and he was still flat broke. The dog was the only thing he had left to sell. “It’s the only thing I could sell,” he says. Producers wanted the script. They just didn’t want Stallone to play Rocky. The offers kept climbing until they reached $360,000. His answer never changed: he plays Rocky or he walks. “I’ve literally crawled through every gutter in New York,” he says. He was sure he would never get a chance like this again. In the end, the studio gave in. Reportedly he was paid $35,000 for the script. The first thing he did was buy his dog back and put him in the movie. Rocky won three Oscars and became one of the biggest hits of its time. This November, a film about Stallone’s fight to make it, I Play Rocky, comes out in theaters. The case for the studio: Stallone was an unknown actor with almost no credits. Nobody knew if a boxing movie could work, and $360,000 for a first script was a fortune. So was saying no the best bet in Hollywood history, or just the luckiest?