Looking back on the end of the ’90s, few things were as exciting as the release of the new Star Wars films. It had been nearly two decades since Return of the Jedi was released and fans thought they would never return to a galaxy far, far away ever again. By the time The Phantom Menace was released, it was maybe the most highly anticipated film of all time.

While the first Star Wars films were obviously massive successes, by the time the prequels came out, this was one of the most iconic brands in the world. Needless to say, plenty of actors wanted to take part in this new trilogy and be a part of Star Wars history. Here are some of the actors who were almost cast in the Star Wars prequels.

Michael Angarano/Anakin Skywalker

The role of young Anakin Skywalker in The Phantom Menace was a very tough role to cast. George Lucas needed to find a young actor who had the range to show audiences he could one day become Darth Vader.

The search for the right actor was a long one, looking at thousands of kids. It eventually came down to Jake Lloyd and Michael Angarano (Red State, Almost Famous). In a behind-the-scenes do

cumentary of the film, Lucas decided that while Angarano was the better actor, Lloyd would be more comfortable with the film-making process. Given how ill-suited Lloyd seemed for the role, perhaps Lucas made the wrong call.

Vinette Robinson/Padme

Vinette Robinson has had a solid acting career in British television, appearing prominently in shows like Sherlock and The A Word. However, her career almost started off in a much bigger way.

Robinson recalls that her very first audition was for Padme in The Phantom Menace. The role that eventually went to Natalie Portman would have been a solid way to start out as an actor. Though she didn’t get the role, it’s interesting that Lucas was considering an actor of color for the mother of Luke and Leia Skywalker.

Leonardo Dicaprio/Anakin

With Attack of the Clones, the second installment in the prequel series, Lucas needed an older actor to step into the Anakin role. Despite poor reaction to The Phantom Menace, this role became heavily sought out among Hollywood’s young stars.

Leonardo DiCaprio is one of those actors who is rumored to be up for every role, but he himself confirms he was offered this part. He explains that the reason he turned it down was simply that he wasn’t ready to join the big budget world. To DiCaprio’s credit, he has become one of film’s biggest stars without going down the franchise path.

Gary Oldman/General Grievous

Gary Oldman is one of the most acclaimed actors working today. He has given highly praised performances in films like Sid and Nancy and Leon: The Professional, won an Oscar for The Darkest Hour and starred in the Harry Potter series and Nolan’s Batman series. To add Star Wars to that resume would be even more impressive.

Oldman has in fact been cast as the voice of General Grievous in Revenge of the Sith. However, Oldman was forced to pull out of the film as it was being made without Screen Actors Guild members. It’s sad that such a technicality would prevent Oldman from joining another iconic franchise.

Ryan Phillippe/Anakin

Ryan Phillippe was another of the popular young actors who was considered for taking over the Anakin Skywalker role in Attack of the Clones. Apparently, Phillippe pursued the role strongly and was able to get as far as reading for the part opposite Natalie Portman.

In the end, Phillippe claims it came down to him being the wrong age to play opposite Portman’s Padme. That seems like a safe bet, as Phillippe is actually a few years older than Portman who was meant to play the older character.

Paul Walker/Anakin

One of the great tragedies in Hollywood in recent years was the death of Paul Walker. The young actor was killed in a car accident, leaving behind a career that was far too short. Walker was most known for his role as Brian O’Connor in the Fast and Furious franchise, but he was nearly a part of an even bigger film series.

Like Phillippe, Walker was very invested in getting the role. He admits that so many young actors were up for the role that it’s hard to know how close he came. In the end, it was Walker’s Takers costar Hayden Christensen that got the part.

Joseph Fiennes/Obi-Wan

While young Hollywood was competing for the role of Anakin, the role of young Obi-Wan was another coveted role. Sir Alec Guinness made the role famous, but Ewan MacGregor impressed many fans with his performance in the prequels.

MacGregor’s final competition for the role was Joseph Fiennes. The Shakespeare in Love actor met with Lucas and might have gotten the role if not for a very critical child. Fiennes explains that the director introduced Fiennes to his daughter who was less than impressed. He recalls, “His daughter turned around and said ‘I don’t like this guy. He’s weird. I don’t like him.’ And that’s how my audition went”.

Tupac Shakur/Mace Windu

Tupac Shakur is one of the most celebrated musical artists of all-time. Before his tragic murder, Tupac was known for his aggressive and poetic rap verses and his music still resonates with fans to this day. However, Tupac was also a very talented actor. And it just so happens, he was a Star Wars fan as well.

A friend of Tupac confirms that the rapper was asked to audition for the role of Mace Windu. As he says, “He was telling me that he was supposed to read for George Lucas and them. They wanted him to be a Jedi”. Seeing as Tupac died in 1996, it would seem like Lucas was considering this casting quite far in advance.

Benicio Del Toro/Darth Maul

Despite all its faults, The Phantom Menace did provide a rather memorable villain. Darth Maul, the silent Sith assassin had a cool character design and provided some of the film’s most memorable moments, but was sadly short-lived.

The character was originally written to play a larger role and Benicio Del Toro was cast in the part. Del Toro eventually backed out after Lucas trimmed the role and cut many of his lines. Del Toro would later join the Star Wars universe as DJ in The Last Jedi.

Michael Jackson/Jar Jar Binks

Much to George Lucas’ chagrin, the most famous – or infamous – aspects of The Phantom Menace is Jar Jar Binks. The CGI character was meant to be the fun comic relief in the film, but ended up being highly irritating cartoon. In a bit of casting that might have made the character even more bizarre, singer Michael Jackson wanted the part.

Ahmed Best, the actor who eventually performed the part recalls Lucas telling him Jackson initially wanted the part, but wanted to play him in prosthetic make-up rather than CGI. Though hard to imagine, Jackson’s casting would likely have made the character even more unbearable.