The Most Horrible Roles of 10 A-List Celebrities

George Clooney at Carousel of Hope Ball

No career of any kind is complete without a few mistakes, and some of Hollywood’s biggest stars know this first-hand.  Many of the world’s most famous actors and actresses have admitted that they’ve taken on film roles that they regret.  These poor performances can be tied to  a number of things; however, no matter the reason,these roles have left an ugly stain on many careers.  Some have not been lucky enough to recover from these awful roles, and their careers have fallen into oblivion. Fortunately for Hollywood’s best and brightest, many have been able to recover and enjoy long-lasting careers even after taking on an ill-fitting role.  Here are the most horrible roles of 10 A-list celebrities.

10. Colin Farrell – Alexander the Great

In the 2004 film, Alexander, Farrell played the title role of the legendary king of Macedonia. Although the film depicted one of history’s most infamous times, it fell short of the expectations from both viewers and critics.  The movie received terrible reviews and many felt as though it was an inaccurate depiction of historical events.  The role is considered Farrell’s worst and resulted in a 2005 Golden Raspberry Award nomination for worst actor.

9.Vince Vaughn – Norman Bates

Norman Bates is one of the most infamous characters in literary and film history.  Unfortunately for Vince Vaughn, his portrayal of Bates in the 1988 remake of Psycho was nothing other than infamously horrible.  The movie itself was considered one of the worst remakes of all-time, and Vaughn’s performance wasn’t too far behind.  Film critic Roger Ebert, who felt that Vaughn was not the right actor for the role stated: “One problem is the casting of Vaughn in the Norman Bates role. He isn’t odd enough. Norman’s early dialogue often ends in a nervous laugh. Anthony Perkins, in the original, made it seem compulsive, welling up out of some secret pool of madness. Vaughn’s laugh doesn’t seem involuntary. It sounds as if he intends to laugh. Possibly no actor could have matched the Perkins performance, which is one of the unique creations in the cinema, but Vaughn is not the actor to try.”

8. John Wayne – Genghis Khan

No legendary career is without a few mistakes, and John Wayne is no exception.  Wayne’s 1956 portrayal of Mongolian ruler Genghis Khan in the film The Conqueror is largely considered the worst role of his career.  Aside from the fact that Wayne is nowhere near Mongolian, the traditional western film star just wasn’t a good fit for the role.

7. Sean Connery – Robert MacDougal

Sean Connery, best known for his role as sly detective James Bond, attempted to relive his days as a fast paced hero in the 1999 film Entrapment.  Unfortunately, Connery’s performance wasn’t well received and many believe that he was not a good fit for the role of thief Robert MacDougal.  Some viewers think that Connery was simply too old at the time to pull of the role convincingly.

6. Angelina Jolie – Margaret Russell

In the 2006 film, The Good Shepherd, Angelina Jolie was cast in one of the film’s starring roles. Jolie’s character, Margaret Russell, was a woman who seduces and becomes pregnant by her friend’s brother.  Although the film received decent reviews, many felt that Jolie was miscast in the role of Russell because she could not convincingly play a submissive woman who was willing to wait around for a man while he traveled around Europe.

5. Brad Pitt – Achilles

Brad Pitt’s role as Achilles in the 2004 film, Troy, is largely considered one of his worst performances.  Although the film was a box office success, many found fault with Pitt’s performance and felt that he failed to “rise to the challenge.”  One reviewer suggested that Pitt’s inability to convey deep emotion is what resulted in his short-comings in the role.

4. Natalie Portman – Evey Hammond

In the 2006 comic based film, V for Vendetta, Natalie Portman took on the role of fictional character Evey Hammond.  The film was a box office success and also earned many positive reviews; however, Portman’s performance has been considered one of her worst. According to GamesRadar’s list of the worst miscastings, Portman was not a good fit for the role because: “Portman is a nimble actress and her big-eyed portrayal of Evey shines in places – those places where she’s utterly silent. The big-vowelled pantomime accent smashes the rest of the performance like a fat-mouthed wrecking ball.”

3. Keanue Reeves – Jonathan Harker

In the 1992 horror film, Bram Stoker’s Dracula, Keanu Reeves stars as Jonathan Harker, a young man who ends up as a guest in Count Dracula’s home.  Although Harker is meant to be smart and inquisitive, Reeves’ performance did not accurately depict the character. Reeves’ portrayal of Harker has been widely criticized with one reviewer stating” “Reeves’ lobotomized performance robbed Harker of the intelligence that should define him, and next to Gary Oldman’s Dracula he barely registers as a screen presence at all.”

2. Ben Affleck – Daredevil

The 2003 film Daredevil marks one of Ben Affleck’s worst movie roles.  Affleck, who took the role because Daredevil was his favorite childhood comic, said that he “didn’t want someone else to do it, because I was afraid that they would go out and do it different from the comic and screw it up.”  Ironically, Affleck ended up doing exactly what he was afraid of. Affleck has since acknowledged that the film did not turn out as he planned.  However, it did not deter him from taking another shot at a comic themed film and he will appear as Batman in the 2016 film Batman v Superman: Dawn of Justice.

1. George Clooney – Batman

The 1997 film Batman & Robin has gone down in history as one of the worst Batman films ever, and George Clooney’s portrayal of Batman has gone right along with it.  One reviewer dubbed Clooney “the big zero of the film” while Clooney himself has been very critical of his role saying that he may have “killed the franchise.”  Due to negative reviews on almost every aspect of the film, the Batman & Robin was never pursued.

(Photo by Christopher Polk/Getty Images)

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