5 Actors Who Could Have Saved the ‘Star Wars’ Prequels

Let’s be real, there were a lot of problems with the Star Wars prequels from Midichlorian counts to endless Trade Federation politics. In the end, not a lot could made the prequels good movies, but at least these actors would have made them a hell of a lot more fun:

1. Tupac as Mace Windu

Tupac Shakur, Splash News, Revenge of the Sith, Samuel L Jackson, Industrial Light & Magic, 20th Century Fox
Splash News/20th Century Fox via Everett

According to Rolling Stone, Tupac Shakur (rapper and headband enthusiast) allegedly read for the role of Jedi Master Mace Windu. Rick Clifford, who worked as an engineer at Death Row Records, said that Tupac had auditioned for a role in an upcoming George Lucas film, “He was telling me that he was supposed to read for George Lucas and them. They wanted him to be a Jedi. I’m serious. Samuel L. [Jackson] got Tupac’s part. [Tupac] said [to me], ‘Old man, keep your fingers crossed.””

The part later went to Samuel L. Jackson and filming for The Phantom Menace began in 1997, less than a year after Tupac’s death. We’re not saying Tupac would have done a better job than Jackson, but it would have been really cool to see a Tupac hologram a decade earlier.

2. Michael Jackson as Jar Jar Binks

Michael Jackson, Phantom Menace, Ahmed Best, Industrial Light & Magic, 20th Century Fox
Daniel Deme via WENN/20th Century Fox via Everett

“Ani are you okay?” In an interview with Vice, Jar Jar Binks actor Ahmed Best said Michael Jackson had repeatedly lobbied Lucas for the part of Jar Jar, “That’s what George told me… He said, ‘Well, Michael wanted to do the part but he wanted to do it in prosthetics and makeup like Thriller.’ George wanted to do it in CGI. My guess is ultimately Michael Jackson would have been bigger than the movie, and I don’t think he wanted that.”

That’s right, MJ wanted to dress up Thriller style which is so much cooler than what we got. Perhaps it worked out for the best though. Jar Jar Binks became one of the most hated figures of 2000s, while Jackson struggled with his own PR problems.

3. Benicio Del Toro as Darth Maul

Benicio Del Toro, Phantom Menace, Ray Park, Industrial, Light & Magic, 20th Century Fox
FayesVision via WENN/20th Century Fox via Everett

Benicio Del Toro is set to play the major villain in Star Wars: Episode VIII, but the Oscar-winning actor could have joined the Star Wars franchise a decade earlier. According to Making Star Wars, Del Toro was initially offered the role of Darth Maul in The Phantom Menace, but turned it down because of the lack of lines and screen time.

Darth Maul actor Ray Park did an amazing job, but one of the biggest issues with the prequels was the carousel of one-dimensional villains. Had Del Toro accepted the role on his own terms, Darth Maul could have been fleshed out into a complete, recurring villain.

4. Gary Oldman as General Grievous

Batman Begins, Gary Oldman, Warner Brothers, Revenge of the Sith, Industrial Light & Magic, 20th Century Fox
Warner Brothers via Everett/20th Century Fox via Everett

In 2004, it was reported that Gary Oldman (Batman‘s Commissioner Gordon and Harry Potter‘s Sirius Black, in other words the coolest mother fucker in the world) had agreed to play villain General Grievous in Revenge of the Sith. However, Oldman later backed out of the film after he learned that Lucas was using non-union actors, “George Lucas and gang agreed to hire Gary Oldman if he in fact would become a union buster, and perform work illegally overseas. As a resident of America, and also a member of SAG, out of respect and solidarity with the other members, he could not and would not consider violating his union’s rules.”

5. Literally Anyone else as Anakin Skywalker

The Great Gatsby, Leonardo DiCaprio, Warner Brothers, Revenge of the Sith, Hayden Christensen, Industrial Light & Magic, 20th Century Fox
Warner Brothers via Everett/20th Century Fox via Everett

Ryan PhillippePaul Walker, Christian BaleColin Hanks, and Leonardo DiCaprio were all considered for the part of Anakin Skywalker. In an interview with Shortlist, DiCaprio admitted that he “just didn’t feel ready to take that dive. At that point.” DiCaprio went on to make Gangs of New York, Catch Me If You Can, and The Departed instead, so he probably make the right decision, but we can’t help but think about the alternate universe where Leo finally won an Oscar for playing Anakin Skywalker.

The role eventually went to Hayden Christensen. Christensen by himself is not a bad actor, but the writing (“I don’t like sand“) and lack of chemistry with co-star Natalie Portman ruined the prequels, especially Attack of the Clones. However, the decision to cast Christensen over actors like DiCaprio and Bale becomes even more baffling when you realize that he was chosen specifically for his chemistry with Portman.

Actually you know what, maybe nothing could have saved these movies.