Some of Hollywood’s biggest stars turned down iconic roles that would have made them hundreds of millions of dollars.
Sean Connery lost $815 million by rejecting Gandalf in Lord of the Rings, Matt Damon walked away from $400 million for Avatar, and Will Smith passed on The Matrix for a movie that flopped.
These decisions cost actors more money than most people make in a lifetime.
Every actor faces moments where a single decision can change the trajectory of their entire career. Sometimes they choose wisely. Sometimes they walk away from the biggest payday of their lives.
The difference between saying yes and saying no to the right role can be worth hundreds of millions of dollars. When you factor in sequels, merchandise royalties, and what Hollywood calls “backend points” (a percentage of every dollar a movie makes), a single contract signature can be worth more than a lifetime of regular acting jobs.
Here are the 25 most expensive rejections in entertainment history, ranked by how much money the actors left on the table. All figures are adjusted to 2026 dollars to show the true scale of what they lost.
1. Sean Connery Turns Down $815 Million for Lord of the Rings
In the late 1990s, New Line Cinema faced a terrifying gamble. They had committed $281 million to film the entire Lord of the Rings trilogy back to back in New Zealand. To reduce their risk, they desperately wanted a major star to anchor the production.
Their target was Sean Connery, the original James Bond. The studio offered him a deal that remains one of the most lucrative in Hollywood history: $10 million per film (totaling $30 million for all three movies) plus 15% of the worldwide box office gross for the entire trilogy.
Connery read the books. He read the script. He even watched footage. His response became legendary: “I read the book. I read the script. I saw the movie. I still don’t understand it.” He turned down the role of Gandalf.
The trilogy went to Ian McKellen instead, who earned approximately $31 million total with no percentage of the gross. For McKellen, it was a career-defining performance. For Connery, it was financial catastrophe.
The three Lord of the Rings films grossed nearly $3 billion worldwide. Connery’s 15% stake would have been worth $450 million in 2001 dollars. Adjusted for inflation to 2026, that’s $792 million. Add in his $30 million base salary (worth $52.8 million today), and Connery walked away from $844.8 million.
Instead, Connery chose to star in The League of Extraordinary Gentlemen in 2003. The film grossed only $179 million, lost the studio an estimated $12 million, and was such a critical disaster that Connery retired from acting in 2005. He earned about $17 million from the film, or $29.9 million in today’s dollars.
His net loss: $814.9 million. It remains the largest single financial mistake in the history of talent management.
2. Matt Damon Chooses Loyalty Over $400 Million
In the mid-2000s, James Cameron approached Matt Damon for the lead role in Avatar. Cameron was blunt: he didn’t need a big name and would cast an unknown if necessary. But to sweeten the deal, he offered Damon 10% of the film’s box office gross.
Damon was already committed to The Bourne Ultimatum with director Paul Greengrass. He felt that leaving the production would betray his collaborators. He turned down Avatar. The role went to Sam Worthington, then virtually unknown.
Avatar went on to gross over $2.9 billion worldwide, becoming the highest-grossing film of all time. Damon’s 10% stake would have been worth between $250 million and $290 million at the time. In 2026 dollars, that’s between $370 million and $429 million.
Damon earned an estimated $20 million for The Bourne Ultimatum, worth about $29.6 million today. His net loss: somewhere between $340 million and $400 million.
Damon has since joked that no other actor in history has left more money on the table, saying that if he had taken the role, he would be discussing it “in space” due to the wealth it generated. James Cameron, however, has been less sympathetic, essentially telling Damon to “get over it” since he’s already one of the biggest movie stars in the world.
3. Will Smith Picks Wild Wild West Over The Matrix
In the late 1990s, Will Smith was the biggest action star in Hollywood, coming off Independence Day and Men in Black. When the Wachowskis pitched him The Matrix, they tried to explain their revolutionary “bullet time” visual effects.
Smith couldn’t visualize it. He chose Wild Wild West instead, a steampunk western he believed was a safer bet for a summer blockbuster. Smith later admitted, “I would have messed it up. I wasn’t mature enough as an actor.”
The role of Neo went to Keanu Reeves, who negotiated significant backend points. For the sequels, Reeves’ star power was so high that he commanded roughly $1 million per line of dialogue. His total earnings from the Matrix trilogy exceeded $200 million, or about $376 million in 2026 dollars.
Smith earned $7 million for Wild Wild West, which bombed at the box office. In today’s money, that’s $13.2 million. His net loss: $362.8 million.
More damaging than the money was the career impact. Reeves became the face of a philosophical action genre that defined a generation. Wild Wild West remains one of the rare failures on Smith’s otherwise dominant 1990s resume.
4. Téa Leoni Turns Down Friends for a Show That Flopped
Before Jennifer Aniston became Rachel Green, the role was offered to Téa Leoni. She turned it down to star in The Naked Truth, a sitcom that lasted only two seasons.
Friends ran for 10 seasons and became one of the most profitable shows in television history. Today, each main cast member earns $20 million per year in residuals, more than 20 years after the show ended.
If Leoni had taken the role and negotiated similar syndication points, she would have earned over $500 million in lifetime residuals and become a global icon. Instead, The Naked Truth paid standard sitcom wages for two seasons and disappeared.
Her net loss is difficult to calculate precisely because it involves decades of residual income, but conservative estimates place it above $500 million in lifetime earnings.
5. Tom Selleck Loses Indiana Jones to a Contract Dispute
Tom Selleck was George Lucas and Steven Spielberg’s first choice for Indiana Jones. He screen-tested for the role. He was officially offered the part for Raiders of the Lost Ark.
There was just one problem: Selleck was already under contract to CBS for the pilot of Magnum, P.I. CBS refused to release him. The role went to Harrison Ford instead.
In a cruel twist of fate, a writers’ strike delayed Magnum production for six months. That was exactly the window Selleck would have needed to film Raiders. By the time the strike ended, the movie had already been cast.
Selleck became a TV icon through Magnum, eventually earning $500,000 per episode at the show’s peak (about $1.76 million today). But he missed the chance to lead one of the most successful film franchises in history.
The Indiana Jones franchise has grossed billions over four decades. Ford’s participation points are estimated to have earned him over $450 million in lifetime earnings from the role. Selleck’s annual Magnum salary, while impressive, was worth about $38.7 million per year in 2026 dollars.
The difference between TV stardom and film franchise immortality cost Selleck an estimated $450 million or more over his lifetime.
6. Al Pacino Doesn’t Understand Star Wars
In 1977, Al Pacino was the most sought-after actor in Hollywood. He was offered the role of Han Solo in Star Wars at a time when he could essentially have any part he wanted.
Pacino turned it down because he didn’t understand the science fiction language of the script. “I can’t play something if I don’t speak the language,” he said. He later joked that he was simply “in the mood to make Harrison Ford a career.”
If Pacino had negotiated a deal similar to Alec Guinness, who took a percentage of gross receipts instead of a flat fee, he would have earned upwards of $90 million from the first film alone. With sequels and merchandising over the decades, the total loss likely exceeds $300 million in 2026 dollars.
Pacino remained a legend either way, but he missed out on becoming part of the most valuable film franchise in history.
7. John Travolta Chooses Pulp Fiction Over Forrest Gump
In 1994, John Travolta was the first choice to play Forrest Gump. He turned it down to star in Quentin Tarantino’s Pulp Fiction instead.
When Paramount refused to fund the iconic running-across-America sequence, Tom Hanks and director Robert Zemeckis personally funded the scene. In exchange, Hanks negotiated a percentage of the film’s gross receipts instead of taking a salary upfront.
Forrest Gump grossed over $678 million worldwide. Hanks earned an estimated $60 million to $65 million, worth about $127 million to $138 million in 2026 dollars.
Travolta would have been offered a similar deal. Instead, he earned approximately $7 million for Pulp Fiction (about $14.8 million today). His net loss: $112.4 million.
However, Travolta has stated he has no regrets. Pulp Fiction transformed him from a “disco-era has-been” into a cool, gritty leading man and saved his career. The role allowed him to find the story he was “truly meant to tell.” Sometimes the right career move isn’t the most profitable one.
8. Emily Blunt Contractually Blocked from Black Widow
Emily Blunt was the first choice to play Natasha Romanoff (Black Widow) in Iron Man 2. She wanted the role. Marvel wanted her for the role.
But Blunt was contractually obligated to appear in Gulliver’s Travels, a film that bombed critically and commercially. She couldn’t get out of the contract. The role went to Scarlett Johansson instead.
Johansson has since earned over $100 million across her Marvel Cinematic Universe appearances. Blunt described losing the role as “a heartbreaker.” Her estimated loss: over $100 million in a career that would have redefined her action-star credentials.
9. Michelle Pfeiffer Says No to Silence of the Lambs
Michelle Pfeiffer was the first choice for Clarice Starling in The Silence of the Lambs. She turned down the role because she was “trepidatious” about the script’s portrayal of evil.
Pfeiffer specifically disliked the ending, noting that “evil won in the end” and she didn’t want to “put that out into the world.” She had recently become a mother and was reevaluating the types of projects she wanted to pursue.
Jodie Foster took the role and won an Academy Award. The film became a cultural phenomenon and cemented Foster’s status as one of Hollywood’s most respected actresses.
While the financial loss is harder to quantify than franchise roles, Pfeiffer missed out on Oscar glory and a career-defining performance. She later said her only regret was missing the chance to work with director Jonathan Demme again.
10. Molly Ringwald Finds Pretty Woman “Icky”
Molly Ringwald was offered the lead role in Pretty Woman when it was still titled $3,000. She was going through a “weird in-between stage” of her career after her John Hughes teen movies.
Ringwald found the story “icky” and turned it down. Julia Roberts took the role for $300,000 upfront and became an overnight superstar. The film grossed $463 million worldwide and launched Roberts into the A-list stratosphere.
Ringwald later reflected that “Julia Roberts is what makes that movie” and expressed no regrets about the missed payday. Still, her career never reached the same heights it might have if she had taken the role.
11. Terrence Howard Takes a Pay Cut and Loses War Machine
Terrence Howard was the original James Rhodes (War Machine) in Iron Man. For the sequel, the studio offered him a 90% pay cut. Howard refused, believing he deserved more after the first film’s success.
Don Cheadle took the role and has played War Machine for over a decade across multiple Marvel films. Howard’s refusal to accept the reduced salary cost him an estimated $50 million in cumulative earnings from the Marvel Cinematic Universe.
12. Burt Reynolds Says No to James Bond
In the 1970s, Burt Reynolds was offered the role of James Bond. He turned it down, believing that an American shouldn’t play the iconic British spy.
The Bond franchise has generated billions in box office revenue and made its leading actors internationally famous. Reynolds’ decision cost him an estimated $200 million or more in lifetime franchise earnings.
13. Leonardo DiCaprio Passes on Spider-Man
Before Tobey Maguire put on the Spider-Man suit, Leonardo DiCaprio was offered the role in the early 2000s. DiCaprio turned it down to focus on dramatic roles and avoid being typecast as an action hero.
The Spider-Man trilogy grossed over $2.4 billion worldwide. While DiCaprio went on to tremendous success in films like The Departed and Inception, he missed out on franchise wealth estimated at $150 million to $200 million.
14. Craig Bierko Declines Friends for a Different Show
Craig Bierko was offered the role of Chandler Bing on Friends before Matthew Perry. He turned it down for another project that quickly failed.
Like Téa Leoni with Rachel, Bierko walked away from $20 million per year in residuals that continues to this day. His lifetime loss exceeds $400 million.
15. Jon Favreau Chooses Swingers Over Friends
Jon Favreau was also offered the role of Chandler Bing. He turned it down to focus on his independent film Swingers, which he wrote and starred in.
While Favreau missed out on hundreds of millions in Friends residuals, his decision arguably worked out. Swingers launched his career as a director and producer, leading him to helm Iron Man and create The Mandalorian. Today, Favreau is more powerful in Hollywood than any of the Friends cast members.
This is one of the rare cases where turning down massive money was actually the right long-term career move.
16. Jack Nicholson Says No to The Godfather
Jack Nicholson was considered for the role of Michael Corleone in The Godfather. He turned it down, and Al Pacino took the role instead.
The Godfather became one of the most critically acclaimed and financially successful films in history. Pacino’s performance made him a legend. Nicholson’s decision cost him an estimated $50 million to $100 million when accounting for the original film and its sequels.
17. Gwyneth Paltrow Turns Down Titanic
Gwyneth Paltrow was offered the role of Rose in Titanic before Kate Winslet. She turned it down to star in other projects.
Titanic became the highest-grossing film of its era at $2.2 billion worldwide. While Winslet became a global superstar, Paltrow missed out on both the iconic role and an estimated $50 million to $75 million in earnings.
18. Matthew Broderick Chooses Inspector Gadget Over The Matrix
Before Will Smith was offered The Matrix, Matthew Broderick was considered for the role of Neo. He turned it down to star in Inspector Gadget.
Inspector Gadget was a critical and commercial failure. The Matrix made Keanu Reeves $200 million across the trilogy. Broderick’s loss: over $200 million.
19. Hugh Jackman Almost Wasn’t Wolverine
While Hugh Jackman eventually got the role, Dougray Scott was originally cast as Wolverine in X-Men. Scott had to drop out due to scheduling conflicts with Mission: Impossible 2.
Jackman went on to play Wolverine in nine films over 17 years, earning an estimated $100 million from the franchise. Scott’s loss in having to withdraw from the role cost him his chance at franchise superstardom.
20. Christina Applegate Turns Down Elle Woods
Christina Applegate was offered the role of Elle Woods in Legally Blonde before Reese Witherspoon. Applegate turned it down because she had just finished playing a “ditzy blonde” on Married… with Children and didn’t want to be typecast.
Witherspoon made the role iconic, earning $15 million for the sequel and launching herself into the A-list. Applegate’s estimated loss: $30 million to $50 million from the franchise.
21. Vince Vaughn Says No to Mr. and Mrs. Smith
Vince Vaughn was considered for the role of John Smith in Mr. and Mrs. Smith before Brad Pitt. Vaughn declined, and Pitt took the role alongside Angelina Jolie.
The film grossed $487 million worldwide. While Vaughn continued to find success in comedy, he missed out on an estimated $20 million to $30 million payday.
22. Sarah Michelle Gellar Passes on Clueless
Sarah Michelle Gellar was offered the lead role in Clueless before Alicia Silverstone. She turned it down for scheduling reasons.
Clueless became a cultural phenomenon and launched Silverstone to stardom. Gellar went on to success with Buffy the Vampire Slayer, but she missed the film that defined 1990s teen comedy.
23. Denzel Washington Turns Down Michael Clayton
Denzel Washington was offered the lead role in Michael Clayton before George Clooney. Washington declined, and Clooney earned an Academy Award nomination for his performance.
While the financial loss was modest compared to franchise roles (estimated at $10 million to $15 million), Washington missed out on critical acclaim and Oscar buzz.
24. Jennifer Connelly Says No to Titanic
Jennifer Connelly was another actress considered for Rose in Titanic before Kate Winslet. She turned it down to pursue other projects.
Like Gwyneth Paltrow, Connelly missed out on the highest-grossing film of the era and an estimated $50 million payday.
25. Nicolas Cage Turns Down Aragorn
Nicolas Cage was offered the role of Aragorn in Lord of the Rings before Viggo Mortensen. Cage turned it down because he didn’t want to spend years filming in New Zealand away from his family.
While Cage didn’t have the same backend deal offered to Sean Connery, he still missed out on an estimated $30 million to $50 million from the trilogy.
What This Teaches About Hollywood Dealmaking
The difference between generational wealth and a regular salary comes down to one thing: backend points.
When actors negotiate for a percentage of a film’s gross receipts (the total box office before expenses), they become partners in the movie’s success. A 10% or 15% gross stake in a billion-dollar film can be worth more than 20 years of traditional acting salaries.
Studios often offer “net points” instead, which sounds similar but is essentially worthless. Hollywood accounting ensures that most films never show a profit on paper, even when they gross billions. Net points mean you get paid after the studio deducts expenses, and the studio can define those expenses however it wants.
The actors who lost the most money were those who turned down “first dollar gross” deals, where you get paid a percentage of every ticket sold from day one. These deals are only offered to the biggest stars for the most important roles.
Sean Connery, Matt Damon, and Will Smith all walked away from first dollar gross deals worth hundreds of millions. Their mistakes weren’t just about picking the wrong movie. They were about not understanding which opportunities come with ownership stakes that create lasting wealth.
When Saying No Was Actually Smart
Not every rejection on this list was a mistake. Jon Favreau turned down Friends residuals but became one of the most powerful producers in Hollywood. John Travolta chose Pulp Fiction over Forrest Gump and saved his career from obscurity.
Sometimes the right career move isn’t the most profitable one. An actor who takes every high-paying role becomes a commodity rather than an artist. The actors who maintain creative control often build more sustainable careers, even if they miss out on immediate paydays.
But when an actor turns down a role because they “don’t understand the script” (Connery, Pacino, Smith), or because they’re locked into a contractual obligation for a movie that flops (Selleck, Blunt), the loss is pure. There’s no silver lining, just the knowledge that a single signature could have changed everything.
The Bottom Line
Sean Connery’s $815 million loss for turning down Lord of the Rings remains the single biggest financial mistake in Hollywood history. Matt Damon’s $400 million Avatar miss comes in second. Will Smith’s $363 million Matrix rejection rounds out the top three.
These aren’t just missed paychecks. They’re the difference between being wealthy and being able to buy small countries. They’re the difference between a comfortable retirement and a family fortune that lasts for generations.
For every actor on this list, there was a moment when someone handed them a contract and they had to decide: yes or no. The ones who said no are still acting, still successful, still living better lives than 99.9% of the population.
But somewhere, in a parallel universe, Sean Connery is playing Gandalf and Matt Damon is Jake Sully. In that universe, they’re not just rich. They’re unfathomably, incomprehensibly, generationally wealthy.
And all it would have taken was saying yes.
