1. John Wayne as Genghis Khan, “The Conqueror” (1956)
 

 

Now, if you’re thinking, “Wait, that can’t be right,” rest assured, your eyes are not deceiving you. Hollywood, in an extravagant display of casting insensitivity, chose John Wayne, Duke of the Western film, to play Mongol warrior Genghis Khan. With a Rotten Tomatoes rating of a floundering 11%, this flick, famous for being filmed downwind of a nuclear testing site (yes, you read that right), is a cocktail of wrong on so many levels. Audience reactions were predictably scathing. Wayne, as Khan, parades around with his cowboy drawl, attempting to embody an ancient Mongolian warrior. The film grossed $9 million at the box office, but its reputation remains a cinematic facepalm.
2. Keanu Reeves as Jonathan Harker, “Bram Stoker’s Dracula” (1992)
 

 
Keanu Reeves is many things. He’s Neo, he’s John Wick, he’s Ted ‘Theodore’ Logan, but a British Victorian-era solicitor he is not. His portrayal of Jonathan Harker in Francis Ford Coppola’s “Bram Stoker’s Dracula” is a cornucopia of misplaced casting. Despite the film’s success, garnering three Academy Awards and making a killing at the box office with over $215 million worldwide, Reeves’s British accent was as believable as a unicorn sighting. Reeves himself admitted in later interviews that he was pretty much out of his depth, having been cast amidst heavyweights like Gary Oldman and Anthony Hopkins.
3. Cameron Diaz as Jenny Everdeane, “Gangs of New York” (2002)
 

 
As much as we love Cameron Diaz for her rom-com and comedic prowess, her foray into the world of historical drama in Martin Scorsese’s “Gangs of New York” was…questionable. Diaz played pickpocket Jenny Everdeane amidst a cast of Daniel Day-Lewis and Leonardo DiCaprio. Despite the film’s 10 Oscar nominations and $193 million box office haul, Diaz’s performance seemed more suited for a light-hearted comedy than the gritty streets of 1862 New York. It was akin to dropping a Taylor Swift song in the middle of a Metallica concert – just a bit out of place.
4. Denise Richards as Dr. Christmas Jones, “The World is Not Enough” (1999)
 

 
It’s a well-established fact that James Bond films require a certain suspension of disbelief. But when Denise Richards, renowned for her roles in films like “Wild Things” and “Starship Troopers,” was cast as a nuclear physicist in the 1999 installment “The World Is Not Enough,” disbelief was not just suspended, it was launched into orbit. Despite its financial success, grossing $361 million globally, Richards’ performance earned her a Razzie Award for Worst Supporting Actress. The plot’s attempt to convince us that Richards could decipher the intricacies of a nuclear bomb wasn’t convincing. Like, at all.
5. Sofia Coppola as Mary Corleone, “The Godfather Part III” (1990)
 

 
When Winona Ryder had to drop out of “The Godfather Part III”, Francis Ford Coppola made the dubious decision to cast his daughter, Sofia, in the pivotal role of Michael Corleone’s daughter. Sofia, now a highly respected director, was panned by critics and audiences alike for her wooden performance in a film that was otherwise nominated for seven Academy Awards and netted $136 million at the box office.
6. Hayden Christensen as Anakin Skywalker, “Star Wars: Episodes II & III” (2002, 2005)
 

 
The “Star Wars” prequels are perhaps best known for their infamous dialogue, questionable directing, and one Hayden Christensen. Cast as Anakin Skywalker, the future Darth Vader, Christensen’s performance was as lackluster as a summer rain in Tatooine. Despite this, the films racked up $649 million and $848 million respectively at the box office, proving the force was still strong with Star Wars fans. George Lucas was even nominated for a Golden Raspberry Award for Worst Director, while Christensen bagged the award for Worst Supporting Actor.
7. Mickey Rooney as Mr. Yunioshi, “Breakfast at Tiffany’s” (1961)
 

 
Mickey Rooney, a veteran of vaudeville, and Hollywood, was cast as Mr. Yunioshi, a Japanese landlord in the classic film “Breakfast at Tiffany’s.” Even for the time, Rooney’s portrayal was egregiously stereotypical, and today is widely considered a glaring blight on an otherwise well-loved film. The film itself was a critical and commercial success, securing two Academy Awards and grossing $14 million, but Rooney’s Yunioshi remains a regrettable example of Hollywood’s historic lack of cultural sensitivity.
8. Jesse Eisenberg as Lex Luthor, “Batman v Superman: Dawn of Justice” (2016)
 

 
When we think of Lex Luthor, we think of a bald, charismatic, sinister genius. What we got with Jesse Eisenberg’s portrayal in “Batman v Superman: Dawn of Justice” was a twitchy, eccentric tech bro. The movie was divisive among critics and fans, evidenced by a Rotten Tomatoes rating of just 29%. Still, it managed to pull in a hefty $873 million at the box office. Eisenberg’s odd take on the iconic villain baffled audiences and critics alike, making us wonder if Mark Zuckerberg had somehow stumbled into the DC universe.
9. Vince Vaughn as Norman Bates, “Psycho” (1998)
 

 
Vince Vaughn, known for his comedic chops, had the unenviable task of stepping into the shoes of Anthony Perkins’ iconic Norman Bates in Gus Van Sant’s shot-for-shot remake of Hitchcock’s “Psycho.” Sadly, his performance was less ‘psycho’ and more ‘awkward guy at a party.’ Despite the all-star cast, the film was a box office disappointment, grossing just $37 million against a $60 million budget, and earned a meager 41% on Rotten Tomatoes. Vaughn’s casting seemed as out of place as a clown at a funeral.
10. Kevin Costner as Robin Hood, “Robin Hood: Prince of Thieves” (1991)
 

 
In theory, Kevin Costner playing the legendary outlaw who robs from the rich to give to the poor sounds like a dream come true. The reality, however, was a performance that swung wildly between “Midwestern farm boy” and “British outlaw.” Despite his erratic accent (or lack thereof), the film was a box office success, raking in over $390 million and securing an Oscar nomination for Best Original Song. Costner’s Hood wasn’t so much a prince of thieves as he was a prince of inconsistent dialect coaching.