18 Actors Who Almost Starred In Classic '90s Movies

One of the most fun things to do is think about what could have been if iconic roles were played by actors different from the ones that made them famous. There were a lot of “what ifs” in the 1980s, and just as many in the ‘90s. So, here is our list of 20 actors that almost starred in classic ‘90s films. 

Will Smith – The Matrix

Imagine being presented with two scripts at around the same time. One is Wild Wild West and the other is The Matrix. That’s exactly what happened to Will Smith in 1996 and The Fresh Prince chose… poorly. In a YouTube video posted a few years ago, Smith explained that he did turn down Neo in The Matrix because he didn’t quite understand the pitch from the Wachowskis and made Wild Wild West instead. He admits it feels like a mistake now.

Brad Pitt – The Matrix

Another actor who turned down the Wachowskis and didn't play Neo in The Matrix was Brad Pitt. He has rarely talked about roles he regrets turning down, but at an event with Leonard Maltin at the Santa Barbara International Film Festival in 2020, he admitted to Maltin that he was the first choice to play Neo, but said no. Pitt joked about it, saying, 

At least we go Keanu Reeves in the role, so it wasn't a total loss!

Julia Roberts – Sleepless In Seattle

Sometimes it comes down to timing. That’s what happened to Julia Roberts when she turned down the role of Annie in Sleepless In Seattle. Roberts was committed to another little rom-com called Pretty Woman, so it’s hard to say that she made the wrong choice! Not only did that movie make her a superstar, but even she thinks Meg Ryan and Tom Hanks, one of the best on-screen couples ever, were the right combo for Sleepless, telling InStyle (via ABC), 

As she noted, everything really did work out for the best where movie history is concerned.

Molly Ringwald – Pretty Woman

Speaking of Pretty Woman, the movie was originally a much darker portrayal of prostitution in LA, and instead of Julia Robert’s million-watt smile charming audiences, it was ‘80s legend Molly Ringwald lined up to play Vivian. Ringwald didn’t like the plot, however, as she explained to The Guardian,

And, no one can blame Ringwald for following her gut.

Gwyneth Paltrow – Boogie Nights

Howard Stern is famous for getting a lot of information out of the celebrities he interviews. In 2015, he sat down with Gwyneth Paltrow and talked about some of the roles she’d passed on in her career. The most intriguing, by far, was Roller Girl in Boogie Nights, who was played by Heather Graham, of course. If you’re wondering if she passed because of the nudity, you’re correct. She told the shock jock, 

Paltrow wasn’t the only actor to pass on the script either, Leonardo DiCaprio decided to star in Titanic over Boogie Nights as well. 

Michelle Pfeiffer And Jodie Foster – Thelma & Louise

Geena Davis and Susan Sarandon are so good together as the titular Thelma & Louise it’s impossible to imagine any other actors in the roles, but they weren’t actually the first choices of the producers. After the script was finished, producer Ridley Scott signed Michelle Pfeiffer and Jodie Foster up to star as Thelma and Louise, respectively. As the story goes, it took quite a long time for Scott to decide on a director, a role he would eventually take himself, and in the meantime, Foster and Pfeiffer moved on to other projects, opening the door for Sarandon and Davis. 

Tom Cruise – The Shawshank Redemption

This is a bit of a complicated story. Frank Darabont wrote the script for The Shawshank Redemption based on a short novella by Stephen King. Darabont always had in his mind that he would also direct the film. When he sold the picture to Castle Rock, the production company had a different idea. Rob Reiner, one of the principals in Castle Rock, wanted to direct the movie and have Tom Cruise, instead of Tim Robbins, star as Andy Dufresne and in exchange, Darabont would be paid a huge flat fee for the script. Darabont, as he explained to Vanity Fair, stuck to his guns and eventually took a smaller salary and a bigger percentage of the profits. Smart move. 

Billy Crystal – Toy Story

“To infinity and beyond! With a mutton, lettuce, and tomato sandwich!” It’s safe to say the role of Buzz Lightyear would have been played very differently had the original star offered the role, Billy Crystal, taken it. Instead, turning down the part ended up being one of Crystal’s biggest career regrets. Tim Allen got the role he’s hopefully revisiting soon, almost 30 years after the first movie. Of the decision, Crystal told Yahoo!, 

Many would say that Crystal is correct, and on one else could have played Buzz better.

Nicolas Cage – Lord Of The Rings

One actor who doesn’t seem to regret missing out on a big franchise is Nicholas Cage. According to the Con Air star, he turned down the role of Aragorn in the Lord of the Rings trilogy, a part made legendary by Viggo Mortensen. It doesn’t bother Cage though, as he told Newsweek about it and other roles he passed on, 

Cage is famous for his fandom, so it's good to know he doesn't regret this decision at all.

Janeane Garofalo – Fight Club

Janeane Garofalo is a Gen X icon, so it only makes sense that she would have been up for a role in a great movie (with one of the all-time great Gen X characters), Fight Club. According to Garofalo, director David Finch gave her the script and told her the part was “hers.” Unfortunately, again, according to Garofalo, Edward Norton didn’t like her for the part and lobbied for Courtney Love, who Pitt didn’t like for the role, so they settled on the outstanding Helena Bonham Carter. Norton disputes the claim, but Garofalo has stuck to her story. 

Halle Berry – Speed

It took a while for Halle Berry and Keanu Reeves to work together, finally teaming up in 2019’s John Wick: Chapter 3 - Parrabellum, but it almost happened much sooner than that. As Berry was promoting that movie, she revealed that she planned to star as Annie in Speed, a role eventually filled by Sandra Bullock, of course. As Berry explained to ET,

The original script was quite different, it seems, and when she saw the final product, she felt the sting, adding "Then I see the movie and I'm like, 'Arrrrghh!'"

Michael Madson – Pulp Fiction

If the Quentin Tarantino Universe is real, then Michael Madson has a big part in it. A role he could’ve played twice. Madson played Vic Vega, a.k.a. Mr. Blonde, in Reservoir Dogs and Tarantino wanted him to reprise the part in Pulp Fiction, however, Madson turned down the opportunity, the role of Vic Vega became his brother Vincent Vega and John Travolta revitalized his career. 

Claire Danes – Titanic

It seems there are stories of almost every actress getting a shot at the role of Rose in Titanic, played in the film by Kate Winslet. While not every claim is accurate, one that certainly is, is that Claire Danes was first offered the part. The Homeland actor has no regrets about not taking the job, and had a pretty good reason why, as she explained to Dax Shephard on his podcast Armchair Expert:

Danes even spoke to Leonardo DiCaprio about it, 

The rest is history!

Drew Barrymore – Scream

You’re probably asking yourself why we included a movie that the actor actually starred in. Well, as it turns out, Drew Barrymore was originally supposed to play Sidney in Scream, whom Neve Campbell turned into a role all her own. Instead of playing the lead, Barrymore suggested they flip the script on the horror genre and cast her as a character that would die at the beginning, leaving audiences to wonder if anyone was safe. Alfred Hitchcock would have been proud. 

Samuel L. Jackson – Boogie Nights

In Season 3 of The Family Guy they make a joke about Samuel L. Jackson being in “everything” including the porn movie Brian is directing. One thing Jackson hasn’t done, is play a porn star, though he almost starred as Buck Swope, the character made famous by Don Cheadle in Boogie Nights. According to director Paul Thomas Anderson in the director’s commentary on the DVD. After getting the script from the then-unknown writer/director, Jackson passed on the project, presumably because of the content of the film, as Gwyneth Paltrow did as well. 

What Ifs…

In most movies, there are “dream” actors that producers, writers, and directors envision in a role, but ultimately are never seriously considered for various reasons. In the ‘90s, there were some seriously big names attached to what would become big roles that aren’t included on this list because it was usually just daydreaming.

Take, for example, Mel Gibson as The Dude in The Big Lebowski. That’s right, the Coen Brothers initially hoped Gibson would play the role, but the script didn’t do anything for him, so the part went to Jeff Bridges and the rest of us abide by this decision. 

How about Leonardo DiCaprio as Will Hunting in Good Will Hunting? That’s what the studio wanted, but Matt Damon says he took a page from Sylvester Stallone and stuck his guns as Stallone did with the original Rocky, and insisted he play the lead role. How’d them apples work out? 

Finally, in one of the most bizarre ideas ever, John Malkovich was approached by the studio to play Robert DeNiro’s role (Jimmy Conway) in Goodfellas. Thankfully, for everyone involved, Malkovich backed off, telling GQ,

Hollywood is filled with near-misses and who knows what kind of butterfly effect these have had on history. It’s good to know that audiences have gotten the best options, but it’s fun to think about what could have been.