Citing that he “didn’t get fantasy,” Sean Connery passed up on playing Gandalf in Peter Jackson’s adaptation of The Lord Of The Rings. The role that was eventually given to Ian McKellen earned the actor an award (Best Supporting Actor in a Motion Picture) and an Academy Award nomination for Best Supporting Actor. Carrie Bradshaw, played by Sarah Jessica Parker, is one of the most popular female TV and movie characters of all time, at least in the “chick flick” genre. The role was originally offered to Dana Delany. She later claimed not to regret her decision to turn it down. Molly Ringwald was one of the most sought-after actresses in Hollywood in the 80’s, thanks to the movies she started in like Pretty In Pink and The Breakfast Club. However, the actress has been plagued with obscurity ever since the 90’s. Her fate might have turned out differently had she accepted the role of Vivian Ward in Pretty Woman. The movie was a massive commercial success, earning over $463 million at the box office. Julia Roberts, who eventually played the character, received an Oscar nomination for the role and became regarded as one of the biggest movie stars in the world. Will Smith was initially offered the role of Neo in The Matrix. He turned it down on account of the concept being too complicated, and he didn’t see the film performing well at the box office. Well, we all know how the movie fared. Henry Winkler was approached to play Danny Zunko in the musical film Grease. When he turned it down, John Travolta took on the role. Grease earned $694 million at the box office. The American Film Institute listed Grease at #97 in its 100 Years…100 Passions, which lists the 100 greatest love stories in American cinema. Michelle Pfeiffer was offered the role of Clarice Sterling in Jonathan Demme’s adaptation of The Silence Of The Lambs. She turned it down because she found the movie to be too violent and disturbing. Jodi Foster won the role, and it gave her a second Academy Award for Best Actress. Al Pacino was offered the role of Han Solo in Star Wars. He said he wasn’t interested in playing the role. Harrison Ford took over, and the movie franchise went on to become one of the most successful film series in history, establishing Ford’s superstar status. Kim Basinger passed up on playing Catherine Tramell in Paul Verhoeven’s thriller Basic Instinct. The role was subsequently handed to Sharon Stone. The film became one of the highest grossing films of 1992, earning $352 million at box office. The role is highly regarded as the one responsible for giving Sharon Stone her much needed break. Jeremy Irons was initially appraoched to play Hannibal Lecter in Jonathan Demme’s adaptation of The Silence Of The Lambs. Just like Michelle Pfeiffer when approached to play clarice Sterling, Irons cited the film’s violent content as his reason for turning down the role. Anthony Hopkins took over the role, and it became one of the most defining moments of the actor’s career. Tom Selleck didn’t exactly turn down the role. He was very interested in playing the role. Steven Spielberg and George Lucas both picked Selleck for the role, but a deal couldn’t be reached with Universal Studios, whom Selleck was set to do another film with. As we all know, the role eventually went to Harrison Ford (whom George Lucas was initially reluctant to cast). Although Hugh Jackman is now exclusively associated with Wolverine, the role was intially meant to be portrayed by another actor, Dougray Scott. However, Scott was handpicked by Tom Cruise to play the villain in Mission Impossible, and the 2nd installment of MI overran filming of X-Men by two months. Scott was forced to drop out of production, which cost him a major Wolverine franchise. When Jack Nicholson was approached to play Michael Corleone, he knew that The Godfather would be a great movie. However, at that time, he felt that “Indians should play characters written for Indians.” In the same thread, Nicholson felt that the role of Corleone should be played by an Italian, so he passed up on playing the iconic role. Michael Corleone, played by Al Pacino, was cited by the American Film Institute as the 11th most iconic villain in film history. John Travolta passed up on playing Forrest Gump…huge mistake. In 1994, the film became the highest grossing movie in North America. Tom Hanks was acclaimed for his portrayal of the role, giving him an award for Best Performance by an Actor in a Leading Role at the Oscars. Travolta has since admitted to regretting the decision he made. Sarah Michelle Gellar turned down the opportunity to star in the 1995 sleeper hit, Clueless. The character, Cher Horowitz, the rich, spoiled, yet sweet girl became so endearing to fans that it brought the then-unknown Alicia Silverstone worldwide recognition. The producers of Sister Act agreed that Bette Midler was best suited for the role. Later on, Midler declined to play the role expressing concerns about her fans not wanting her to play the role of a nun. The part was eventually given to Whoopi Goldberg. The film was widely successful, spawning one sequel and a Broadway musical. Thinking that it was just another B-Horror movie, Reese Witherspoon refused to audition for the role of Sidney Prescott in Wes Craven’s critically acclaimed slasher film Scream. The role was played by Neve Campbell instead. Had Jake Gyllenhaal proceeded to play the role of Jake Sully in James Cameron’s Avatar, he would now be holding the honor of starring in the highest grossing film of all time. When the production of Million Dollar Baby was met with delays, Sandra Bullock packed her bags and left. Unfortunately for her, the film was not only a commercial success, it also was universally acclaimed by critics. Its star, Hilary Swank, earned her second Best Actress award at the Oscars. Mel Gibson was initially approached to play the role of Bruce Wayne/Batman in Tim Burton’s 1989 adaptation. Thinking that the movie would be a flop, Gibson passed up on playing the role. In line with Tim Burton films, Batman was criticized for being “too dark.” That didn’t stop the film from being a massive box office success, earning a reported $411 million. Kate Winslet was offered the role of Viola de Lesseps in the 1998 British romantic comedy-drama film Shakespeare in Love. Had she accepted the role, Winslet might have won an Oscar for Best Actress much earlier in her career rather than having to endure 5 losses before winning her first Academy Award in 2009. The Twilight film series brought international attention to its stars Kristen Stewart, Robert Pattinson, and Taylor Lautner. The author of the books on which the films are based, Stephenie Meyer, has stated that Emily Browning was her “ideal Bella.” However, Browning refused to even audition for the part. In an interview, the actress had this to say, “The author at one point stated that I would be her ideal Bella, but I chose not to audition because I was at a point in my career where I wasn’t sure I wanted to work.” Great roles are so hard to come by these days. An even harder thing to snag: an Academy Award. Julia Roberts might have won her 2nd Best Actress award had she accepted the role of Leigh Anne Tuohy in the 2009 film The Blind Side. Roberts turned down the role to do Valentine’s Day, a film directed by Garry Marshall– the man who gave her the career-defining role of Vivian in Pretty Woman. Talk about missing a major shot! When Bruce Willis turned the role of Sam Wheat in the 1990 romantic fantasy film Ghost, he missed the opportunity to play a part opposite his then real-life spouse, Demi Moore, as well as starring in the highest grossing film of 1990. Ghost reportedly earned $505 million at the box office. When Sigourney Weaver turned down the role of Sarah Tobias in the 1988 film The Accused, Jodi Foster took over the role. It earned her the first of two Oscars for Best Actress. Jim Carrey turned down the role of Edward Scissorhands, and it was eventually handed over to Johnny Depp. It turned out to be a groundbreaking roll for him.