In the entertainment world, many actors showcase their impeccable craft which eventually led them to earn an Oscar, which is a prestigious award for artistic and technical merit. There are many talented Oscar-winning actors who left audiences spellbound with their acting s𝓀𝒾𝓁𝓁s. But just like anyone, they have somewhat affected their glamorous career by making the awful decision to let go of famous movies.

Academy Awards stautette [Credit: Academy of Motion Picture Arts and Sciences]Also Read: “It was incredibly isolating”: While Brendan Fraser Won An Oscar For ‘The Whale’, Gwyneth Paltrow Called A Similar Role Her Worst Regret

As a movie gains recognition, audiences automatically get interested in all about it including the casting plans which often surprise many. It’s quite interesting as many famous actors have talked about passing on a movie just to regret it later. Here is the list of five Oscar-winning actors who regretted turning down iconic movies.

Denzel Washington

Denzel Washington

With his artistic s𝓀𝒾𝓁𝓁s, Denzel Washington has left an indelible mark on the entertainment industry gaining critical acclaim and numerous accolades, including 2 Oscars. In 1990, he received his first Academy Award for Best Supporting Actor for his impeccable performance in the war epic movie, Glory. The Cry Freedom actor received a series of Oscar nominations which solidified his status among Hollywood’s most esteemed actors. Meanwhile, for his performance in the 2001 crime-thriller movie, Training Day, he bagged another Oscar for Best Actor. 

Having already received an Oscar, he once confessed to turning down two movies in his acting career with one being Se7en which became an intriguing masterpiece in the film industry. While he did not reveal the reason for rejecting it, he also turned down Michael Clayton, which eventually starred George Clooney.

He recalled in an interview with GQ, 

“With Clayton, it was the best material I had read in a long time, but I was nervous about a first-time director, and I was wrong. It happens.”

The movie ended up getting nominated for seven Oscars winning in three categories including the Best Actor category for Clooney.

Leonardo DiCaprio

Kate Winslet and Leonardo DiCaprio in Titanic

Leonardo DiCaprio, a young hunk who captivated global hearts with his 1997 movie, Titanic left the audience in ultimate surprise by going to extreme lengths for his portrayal in The Revenant (2015). His intense dedication to his craft eventually earned him an Oscar. However, many would not know that he passed on to play the role of p*rn actor Dirk Diggler in Boogie Nights (1997) which eventually went to Mark Wahlberg. 

He told GQ Magazine, 

“Boogie Nights is a movie I loved and I wish I would’ve done. I’m not saying I would have. But it would have been a different direction, career-wise. I think they’re both great and wish I could have done them both. The truth is, if I’d not done Titanic, I wouldn’t be able to do the types of movies or have the career I have now, for sure. But it would have been interesting to see if I had gone the other way.

He was the first choice of director, Paul Thomas Anderson but he chose to star in James Cameron’s epic movie instead. While Wahlberg’s movie was an incredible hit, Titanic had a huge impact on the cinematic world. 

Brad Pitt

Brad Pitt

Brad Pitt is one of the high-profile actors who has made significant contributions to the world of cinema. Winning two Academy Awards in the Best Supporting Actor category for 1996’s 12 Monkeys and 2020’s Once Upon a Time in Hollywood along with numerous awards nominations, he proved that his acting prowess is commendable.

However, he has one major regret turning down the lead role that raised Keanu Reeves to further prominence. He passed on the opportunity to star as Neo in The Matrix as he shared via USA Today, 

“I took the red pill.”

It could have entirely changed his career trajectory but he believed that the role was never his which eventually went to the Speed actor. 

Will Smith

Will Smith won his Best Actor Oscar for King Richard

Just like the Bullet Train actor, renowned actor, Will Smith also turned down the Neo role only to work in his flop movie, Wild Wild West (1999). 

“So I made Wild Wild West [instead],” the Emancipation actor confessed via PEOPLE which he regretted doing for years. “I’m not proud of it.”

However, he joked stating that his portrayal would have ‘ruined’ what Reeves perfectly executed in the franchise. 

 “Keanu was perfect, Laurence Fishburne was perfect, so I probably would have messed The Matrix up. I would have ruined it, so I did y’all a favour.”

Had he worked in the famous film series, his career would have been on a different trajectory but nonetheless, his accomplishments still solidify his position as one of the most bankable stars in Hollywood. Meanwhile, he won an Oscar for his portrayal of Richard Williams in the biographical sports drama King Richard (2021). 

Matt Damon in Avatar

Last but not least, Matt Damon, who bagged an Oscar for Best Screenplay for his 1997 film, Good Will Hunting also has regrets over turning down a major role in a famous project. It is none other than James Cameron’s insanely hit film, Avatar where the director approached him with a lucrative offer of pocketing him with 10 percent of the film’s gross earnings.  

He told GQ in 2019, 

“I’ve left more money on the table than any actor,” referring to a golden opportunity that knocked at his door but he chose to leave it. “He works so infrequently, but his movies, you know all of them. So it feels like he’s made more than he has. I realised in having to say no that I was probably passing on the chance to ever work with him. So that sucked and that’s still brutal. But my kids are all eating. I’m doing OK.”

Things would have been entirely different for the talented actor but it stung him a lot. The role eventually went to Sam Worthington with the film becoming a great success worldwide.

While the entertainment world is ever-evolving bringing actors to the forefront due to many successful projects, the list that could have witnessed another face is quite long. However, their talent has always left their imprint in the industry in one way or another, thus recognizing the hard work they put in their work.

Source: GQ, PEOPLE