10 Iconic Roles These Actors Regretted Turning Down

Actors can often have their careers launched by a particular movie. It may go on to be a hugely successful movie that garners praise from critics and is lavished with awards, firmly establishing the stars who play the leading roles as blockbuster names that are capable of carrying a release to box office success. The decision to take roles in such movies can be a hugely important decision that will define the career that a particular actor might have throughout their life.

In many cases though, actors will miss out on playing the role of a lifetime. It may have been a part that would launch their acting career, bring them plaudits, or perhaps even massive financial rewards. It’s an understandable hazard of working in the movie industry, as a person can only appear in a limited number of releases due to the large amount of time they can take up in schedules. Facing multiple choices, actors might turn down a film because they do not think it will be successful or because they like the idea of another project more. For whatever reason, sometimes actors decide against appearing in a movie and then go on to regret it.

While it may be hard to imagine the roles in this list being played by anyone else, each could have had a very different person portraying them if producers and filmmakers got their original wishes.

10 Michael Madsen - Pulp Fiction


9 Ralph Macchio - Back to the Future

Back to the Future went through a protracted development and production period when the filmmakers were looking to cast the role of Marty McFly. The well-known story is how Eric Stoltz got the gig originally, until he was dropped after his performance was deemed too serious. However, Ralph Macchio of the Karate Kid fame was the first choice to take the star role. The actor turned it down as he misinterpreted the script and thought it would be a fairly silly film rather than the huge success it became. Taking the role may have moved Macchio’s career to the next level and established him as a leading man capable of fronting blockbuster films. Those rewards instead went to Michael J. Fox, leaving Macchio with a relatively limited filmography.

8 Meg Ryan - Pretty Woman

Pretty Woman is perhaps one of the greatest and most successful romantic comedies of all time. When director Garry Marshall first set about casting for the part of Vivian Ward for the film, he had one actress in mind. As the star of hit movies such as When Harry Met Sally and Sleepless in Seattle, it isn't a huge shock that she was the initial first choice to take up the lead role in the new movie. However, Ryan decided to turn down the offer for an unknown reason and instead, the role went to the relatively unknown Julia Roberts. The film itself went on to gross almost $500 million from just a $14 million budget and garnered nominations for best actress for Roberts at the Golden Globe and Academy Awards.

7 Henry Winkler - Grease


Grease is one of the most famous films of all time and is arguably the greatest musical to ever be made in Hollywood. It played a huge part in launching the careers of several personalities and has become a classic of the genre. What is not widely known though is that the part of Danny Zuko was first offered to none other than Henry Winkler. However, fearing that he would be typecast as the same character he had portrayed in Happy Days, Fonzie, he turned down the role. John Travolta was then cast in the part and the film went on to establish him as a major star. Winkler meanwhile later expressed regret over not taking the role as he later realized he had already been typecast before Grease released.

6 Will Smith - Django Unchained

5 Gwyneth Paltrow - Titanic

It is fair to argue that Kate Winslet’s career was launched by her performance in James Cameron’s modern masterpiece, Titanic. Her role alongside Leonardo DiCaprio in the blockbuster has ensured that she will be remembered throughout history, as the film is simply one of the most successful and important ever made. Nevertheless, Winslet was far from the first choice of Cameron and the producers who thought that Gwyneth Paltrow was the ideal candidate. She was given the script and offered the role although the actress turned it down as the script did not particularly impress her. This decision led to Paltrow missing out on being involved in a hugely popular film that grossed more than a billion dollars.

4 Cary Grant - James Bond: Dr. No


Cary Grant may be relatively unknown to modern young moviegoers, yet he is without a doubt one of the most influential leading men in Hollywood’s history. He had an extensive career, appearing in countless films that are considered classics, and is rightly viewed as one of the greatest actors of all time. The veteran actor also had a chance to appear as one of the most iconic roles in the industry when he was offered the role of James Bond in Dr. No. Albert Broccoli, the legendary producer behind the Bond movie franchise, was a close friend of Grant and gave him the first opportunity to take up the part. The actor decided against the move though, as he only wanted to do one film and the job eventually went to Sean Connery, launching his career and immortalizing him.

3 Ryan Gosling - Dallas Buyers Club

Dallas Buyers Club had a rocky development and production period, lasting more than a decade. Numerous actors were attached to the project to portray the title character Ron Woodroof, including Woody Harrelson and Brad Pitt, although the closest anyone came before casting was finally decided was Ryan Gosling. He was originally approached in 2008 about the possibility of taking part and seemed very interested. Continuing financial difficulties though, meant that Gosling eventually pulled out. The part instead went to Mathew McConaughey and the film proved to be a huge success, having strong box office results and positive critical reception. McConaughey went on to win an Oscar for best actor while the movie was nominated for a variety of awards.

2 Kevin Costner - The Shawshank Redemption

The Shawshank Redemption is widely viewed as one of the most exceptional films of the modern era. It received huge plaudits and a large number of awards and nominations, with it appearing regularly on fans and critics' “Top 10” lists. However, filmmakers did not originally envisage the lead role being taken up by Tim Robbins. Instead, the producers first approached Kevin Costner about doing the job and portraying Andy Dufresne. Although, Costner decided against working on The Shawshank Redemption to concentrate on the rather less critically acclaimed Waterworld, leaving the role open to Robbins.

1 Sean Connery - The Matrix / Lord of the Rings


Ever since Sean Connery rose to fame playing one of the most recognizable characters in the movie industry in James Bond, he has been a huge draw for filmmakers. He’s had roles in some of the biggest movies of all time and received critical acclaim for his work in the likes of The Hunt For Red October and Indiana Jones and the Last Crusade. With such a portfolio and plenty of appeal with audiences, it should come as no surprise that Connery was often approached to take on roles, but what is surprising are some of the jobs the veteran actor has turned down.

He turned down the chance to portray Morpheus in The Matrix series of films that later went on to be huge successes, and also spurred the opportunity of being cast as Gandalf. Peter Jackson and co. offered the part of the iconic wizard to the actor and tried to lure him with a percentage of the profits, something that would have netted Connery more than $300 million. The reason for turning down both roles stemmed from the fact he didn’t really understand the story and action in the scripts. He has since publicly expressed his regret and explained that he only took part in The League of Extraordinary Gentlemen as he also didn't understand it but did not want to miss out; another mistake as the film didn't match the performance of Lord of the Rings or The Matrix.

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