Recastings in Hollywood are a dime a dozen. Nearly every film produced at one point had several actors considered to play key roles, even if, in retrospect, it’s impossible to imagine the parts going to anyone else. But when you hear that some of the most iconic roles in Hollywood history almost went another way, they take on a sort of mystique. Truman Capote once intended for Marilyn Monroe to be Holly Golightly, and Eric Stoltz had filmed scenes as Marty McFly; tons of fateful decisions have been made that nearly denied us our on-screen heroes as we came to know them.
As we continue our celebration of the best movie performances of the 21st century, let’s look back at the ones that almost never happened. These serve as the millennium’s biggest what-ifs, or—to borrow a bit of Bill Simmons parlance—sliding doors moments, if you will. What if Jake Gyllenhaal had replaced Tobey Maguire for Spider-Man 2? Or Denzel Washington had agreed to star in Michael Clayton? Or Penélope Cruz had taken on Melancholia? Would the movies live up to the versions we know and love today or take them in an entirely different direction? Is there a universe where Jon Hamm is now halfway to an EGOT thanks to his role in Gone Girl? Let’s attempt to answer the biggest what-ifs of the past 25 years.
What if … Leonardo DiCaprio had explained Huey Lewis songs?
The sliding doors moment: There were a couple of efforts to bring Bret Easton Ellis’s 1991 novel, American Psycho, to the screen. (The most notable of which involved David Cronenberg and Brad Pitt. Now there’s a what-if!) The project didn’t enter serious development, though, until director Mary Harron signed on in 1996. Lionsgate was dead set on Leonardo DiCaprio, whose megawatt star power was exploding after Titanic, for the role of Patrick Bateman—so much so that, at the 1998 Cannes Film Festival, the studio blindsided Harron with an announcement that he would be playing the part. Harron has said that she’d already been talking about the role with Christian Bale, who, despite some memorable parts throughout the ’90s, had not quite broken through yet. She felt that DiCaprio was so wrong for the part—“There’s something very boyish about him,” she would later say—that she flat out refused to meet with him. Lionsgate responded by dropping her from the project and replacing her with Oliver Stone … only for DiCaprio to drop out of the film himself when he was offered the lead role in Danny Boyle’s The Beach. Stone’s departure followed, Harron was reinstated, and soon enough, Bale was making the world’s first “get ready with me” video in Patrick Bateman’s bathroom.
Would it have worked? A 2000 report in The Guardian said that Stone was going to approach the film as more of a straightforward psychological thriller rather than blending in the novel’s social satire, which Harron eventually implemented in the movie. In that case, I’m sure that Leo would have done a fine job, and it would’ve been a pretty run-of-the-mill crime film with no greater legacy.
If DiCaprio had starred in Harron’s version of the film, I’m not sure that it would’ve worked. “Leonardo DiCaprio in a comedic crime thriller” may seem like a layup today, but it took him awhile to grow into the likes of Jordan Belfort and Rick Dalton. Even back then, his morally gray characters like Catch Me If You Can’s Frank Abagnale Jr. played on that boyish charm Harron was concerned about—Patrick Bateman needed to have a real sinister menace to him, a darkness behind the eyes that DiCaprio wasn’t capable of tapping into at the time. Those baby blues and that floppy golden hair simply weren’t giving sociopathic finance bro! Lionsgate be damned, Bale was the right choice all along.
What would be different today? DiCaprio flounders in the role and his stock plummets. He books a comeback role in the late 2000s in some shitty Jason Reitman–type dramedy that gets him an Oscar nomination. Bale never gets jacked for American Psycho and therefore never discovers the power of transforming his body for a role, so he’s … just kind of a normal dude. Somehow, Jared Leto lands Batman Begins. Everybody loses!
The Best Movie Performances of the Century
What if … Tobey Maguire had transformed into Jake Gyllenhaal?
The sliding doors moment: You might ask how studio execs could even consider recasting the face of an astronomically gigantic superhero franchise. Once upon a time (in the heady days of 2002), wearing tights and beating up bad guys wasn’t as secure of a gig as it is now. Spider-Man was a massive success upon its arrival in spring 2002, both financially and critically, and Tobey Maguire’s endearingly meek portrayal of New York City’s web slinger was a huge part of that. Plus, he had inked a three-picture deal when he signed onto the project back in 2000. A sequel was a no-brainer. There was one problem, though: While playing a jockey for Seabiscuit in 2002, Maguire suffered a herniated disc in his back. Reporting from the time indicates that Maguire wasn’t totally up-front about the severity of the injury, and director Sam Raimi found out about it elsewhere. “When I heard that Tobey could be paralyzed from a stunt on set, I realized I couldn’t possibly have him in the picture,” Raimi said in 2004. Plus, rumors swirled that there was already tension between Maguire and Raimi after the actor had declined to participate in a computer scan for special effects during preproduction. Maguire has also acknowledged that his general attitude heading into Spider-Man 2 was “inappropriate”—speculation that the actor is difficult to work with on set (and in poker games) followed him in the tabloids for the rest of his career, so it’s not hard to believe that his reputation played a factor in his recasting.
Enter the man behind cinema’s most unsettling heartthrobs: Jake Gyllenhaal. Raimi said that he offered the role of Peter Parker to the actor, who was coming off 2001’s Donnie Darko, because of how serious he believed Maguire’s back injury to be. “I think [Maguire] is the right Spider-Man. But if I can’t have Tobey, you’re the man for me,” he recalled telling Gyllenhaal. Those involved in the decision also believed that Maguire and Gyllenhaal looked basically identical and that no one would notice the switch: “A year from now? The public wouldn’t know the difference,” an anonymous source close to Maguire (perhaps predicting the meme of the Spider-Men pointing at each other?) told the Los Angeles Times. Columbia officially dropped Maguire from the sequel and was prepared to move forward with Gyllenhaal. Then came another hitch in the plan: Maguire was dating Jennifer Meyer, daughter of Universal Studios COO Ronald Meyer, at the time. She informed her father of the recasting, and, not wanting Maguire’s star power to diminish before his studio put out Seabiscuit, he called in some favors (nay, demands?) with Columbia. After some health exams, fitness tests, and provisions worked into his contract, Maguire was suiting up as Spidey yet again. Who knew that Seabiscuit held so much influence?
Would it have worked? As in, would audiences have believed that Maguire and Gyllenhaal were the same person? I’m going to take a shot in the dark and say no. (Although they did eventually play brothers!) But would Gyllenhaal have been able to lead the film in his own right, if you ignore all of the context of the recasting and the lack of continuity from the first film? Eh … I’m still going with no. Gyllenhaal is a much more versatile and impressive actor than Maguire, as evidenced by the fact that he’s had a much more versatile and impressive career. But Maguire was pitch-perfect for the nerdy, disarming portrait of Peter Parker that Raimi had in mind, and that version of the hero doesn’t really suit Gyllenhaal’s strengths anyway. Even when he’s playing “good” guys, like in Brokeback Mountain or Zodiac, he tends to imbue them with a tendency for outbursts or wild-eyed obsession—not exactly the quietly romantic tone that Maguire was going for with Spidey. It’s no surprise that when Gyllenhaal did eventually make it on-screen in the Spider-Man universe, it was in a villainous role. Now, if we were talking about Spider-Man 3, I would’ve loved to see Jake G shoot some finger guns and sweep Bryce Dallas Howard off her feet in a jazz club. Alas, I think that Spider-Man 2 ultimately worked out the way it was meant to.
What would be different today? Spider-Man 2 is still a box office success, but the legacy of the series as a whole is tarnished, and a third installment is never made. Superhero movies are deemed unsustainable, and studios instead turn to auteur-driven films aimed at adults to win back audiences. The 2000s serve as another Golden Age of Hollywood, at the cost of emo Peter Parker.
What if … Denzel Washington was the guy you buy, not the guy you kill?
The sliding doors moment: There isn’t a huge story here, but it does involve swapping out one titan for another. In 2012, GQ asked Denzel Washington whether there are any roles he regrets turning down. He named two films: Se7en and Michael Clayton. “It was the best material I had read in a long time,” he said of the latter. His ambivalence stemmed from the prospect of working with first-time director Tony Gilroy (who went on to create Andor)—“I was wrong,” Washington later admitted to GQ—so he declined, and George Clooney wound up portraying the fixer.
Would it have worked? Come on, Denzel would’ve absolutely crushed this. Don’t tell my Ringer colleagues this, but … I’m not the biggest Michael Clayton head. I kind of even find it slightly boring. I’m sorry! But if Washington—perhaps the single most magnetic screen presence of all time?—had been in there chopping it up with Karen Crowder and plotting U-North’s downfall, I’d be rewatching it regularly. Just imagine him delivering the “Do I look like I’m here to negotiate?” line and tell me it wouldn’t rock extremely hard. Clooney obviously succeeded in the role, and he ended up on our list of the best performances of the 21st century for a reason, but I think that Washington would have killed with this material.
What would be different today? Washington wins his third Oscar for Michael Clayton and is immediately canonized as one of the all-time greats. Clooney is still a couple of nominations away from his eventual consolation Oscar after his loss for Jay Kelly.
What if … Heath Ledger happened upon $2 million?
The sliding doors moment: Josh Brolin’s rugged exterior seems so suited to the on-the-run Texan Llewelyn Moss in 2007’s No Country for Old Men that it’s hard to picture anyone else taking on the role. But the Coen brothers’ first choice was Heath Ledger, himself coming off a Western take in Brokeback Mountain. Brolin later recalled that the eventual Joker opted out of the picture because he simply needed a break from acting.
Would it have worked? Hell yes! Brolin is fantastic in No Country, and it would be a bummer to lose that performance. But Ledger was on an absolute heater from 2005 to 2008—Llewelyn Moss surely would’ve been another scene-stealing feather in his cap. It’s tough to think about any of the great Ledger performances we’ve missed out on since his death in 2008, but he and the Coens would have been a particularly excellent match.
What would be different today? Ledger’s career from Brokeback Mountain to No Country for Old Men to The Dark Knight is considered one of the most impressive runs any actor’s ever had.
What if … Penélope Cruz had witnessed a planet colliding with Earth?
The sliding doors moment: Most of the entries on this list just involved some fateful recasting for a competitive role, but Melancholia’s Justine was conceived for Penélope Cruz, and the ideas for the film came from letters that director Lars von Trier exchanged with her. If she was so integral to the character, then how the heck did she not end up in the movie? Well, a little motion picture called Pirates of the Caribbean: On Stranger Tides came along. Who could say no? Cruz quite literally jumped ship, and von Trier had to tag in a second-string Justine in Kirsten Dunst.
Would it have worked? Considering how vital Cruz was to the inception of the film and the character of Justine in particular, it seems pretty likely that she would have excelled in the role. She’s had such a varied career, from her work in Pedro Almodóvar’s films to her turns in American blockbusters, and she consistently provides an electric screen presence, so I’m sure that she would’ve risen to the occasion. But it really makes it all the more impressive that Dunst so ably stepped into a performance entirely intended for someone else and turned in one of the best screen roles of the century.
What would be different today? Cruz receives widespread acclaim for Melancholia and Dunst is still just as acclaimed an actress, but Marie Antoinette is (rightfully?) her most celebrated role.
What if … Shiv Roy were Swedish?
The sliding doors moment: In 2010, Lisbeth Salander was the single hottest role in Hollywood. Stieg Larsson’s Millennium book series was a bona fide phenomenon: It sold 100 million copies and crossed over from Larsson’s native Sweden into the United States. The Swedish adaptations of the three novels Larsson penned before his death in 2004, starring Michael Nyqvist and Noomi Rapace, found moderate success in the U.S., but the one-inch barrier had audiences itching for a Hollywood version of their favorite Nordic thriller.
Serial killer whisperer David Fincher signed on to direct the American remake, and although there was a little competition for the role of journalist Mikael Blomkvist (Entertainment Weekly reported that Brad Pitt was in the mix), Daniel Craig was cast pretty quickly. The pierced punk hacker Lisbeth was tougher—there was an extensive casting search that included just about every 20-something white woman in Hollywood. Seriously, check out the “Casting” section on The Girl With the Dragon Tattoo’s Wikipedia page, and you’ll see about 5,000 blue names. I’m not sure how seriously they were all considered, but Kristen Stewart, Natalie Portman, Scarlett Johansson, and Carey Mulligan were all names floated in the trades, until the search reportedly came down to a final four: Rooney Mara (whom Fincher had just worked with on the yet-to-be-released Social Network), Léa Seydoux (coming off Inglourious Basterds and Ridley Scott’s Robin Hood), Sarah Snook, and Sophie Lowe (Snook and Lowe were both steadily working Australian actors who hadn’t broken through in the U.S. yet). We know how that competition ended: Mara dyed her hair black, she pierced her nipple, and the rest is history.
Would it have worked? Unless you’re Australian, the name in the final four that surprised you the most is probably Sarah Snook. Yep, before she was rocking pantsuits and quiet luxury, Shiv Roy herself almost sported an eyebrow piercing and a “Fuck You, You Fucking Fuck” T-shirt. (Actually, I wouldn’t be surprised if that were a Shiv Roy line.) Seydoux seems like a natural choice—she has a hard mystique to her that eventually lent itself to experimental fare like The Beast and would have definitely suited Lisbeth—and Lowe never quite crossed over, so it’s hard to know what her take would have been. But Snook is interesting—many of us weren’t familiar with her until her breakout on Succession seven years after Dragon Tattoo’s release, so I don’t totally know what her vibe would’ve been at the time. She brought a coldness to Shiv that was apt for a cutthroat business environment, but Lisbeth’s icy demeanor is of a slightly different variety, as she exists on the fringes of society and faces horrific abuse. While I think that Snook could’ve made the adjustment for it to work, I don’t know that she would have fully embodied the character the way Mara did.
What would be different today? Snook’s eyebrow piercing never closes up, so it gets written into Succession. Mara’s acting career stalls, and she instead takes an active role with her uncle’s football team, eventually convincing Giants executives to re-sign Saquon Barkley.
What if … Reese Witherspoon had Gone Girl’d Jon Hamm?
The sliding doors moment: Upon its publication in 2012, Gone Girl was heralded as a pulpy bestseller ripe for a movie adaptation. Reese Witherspoon, in the precursor to her Reese’s Book Club days, optioned the book with her production company and 20th Century Fox. Since she wasn’t yet known as a producer, presumably she intended to star in it as well (reporting from the time indicates that playing the role of Amy Dunne motivated her to obtain the rights to the novel in the first place). Director David Fincher (turns out that Fincher plus a buzzy novel equals a sliding doors moment!) had other ideas: “He and I sat down and talked about it and what he wanted the character to be like,” Witherspoon told The Hollywood Reporter in 2014. “He was very candid. He’s like, ‘It’s just not you.’” She said that she understood the decision, and she opted to stay on as a producer while the role ultimately went to Rosamund Pike.
As for Nick Dunne, Jon Hamm has claimed in recent years that the part was initially supposed to go to him, but he had to drop out because of his commitment to Mad Men. In fact, Page Six reported in 2015 that there was some friction between Hamm and Mad Men creator Matthew Weiner because the latter wouldn’t allow his Don Draper out of his contract to take the Gone Girl job. In the end, Ben Affleck got to be the one to flash a grin next to his wife’s missing poster.
Would it have worked? I think that Gone Girl’s leads are impeccably cast. I wouldn’t trade Affleck and Pike as Nick and Amy Dunne for anything. The film served as Pike’s breakthrough, and I believe it’s the single best performance of Affleck’s career. That said, if there were an alternate cut floating around out there featuring Hamm and Witherspoon as the leads, I’d be wildly curious to see it.
As a Mad Men die hard, I would of course love to see Hamm in another big dramatic role (plus, you know, he has all that experience playing a handsome guy who cheats on his wife). He’s from Missouri, where most of the movie is set, so he could presumably throw on a Cardinals hat without protest. It’s harder to imagine him believably having an Xbox addiction, and he’s a bit too polished for the level of smarminess that Affleck taps into to play Nick. But overall, I think that he could’ve pulled it off.
Witherspoon is more of a wild card. She’s a terrific actress who’s tackled a variety of roles in her career—but “ice queen alienated by suburbia” is not one of them. In fact, many of her characters thrive in suburbia, and Amy’s whole persona is supposed to be antithetical to it—it’s easy to see where Fincher was coming from when he decided to go another way. I’m totally open to the idea that she could’ve tackled the role in an unexpected way and succeeded, but it’s hard to picture what it would’ve looked like. I’d love to see it, though!
What would be different today? Pike remains largely unknown, Witherspoon proves everyone wrong and nabs an Oscar nod for Gone Girl, and Hamm crosses over into prestige cinema. Affleck copes with missing out on the role with some distressed smoking.
What if … Amy Schumer had taken us to Barbieland?
The sliding doors moment: When it was announced that a live-action Barbie movie was in development, many wondered what the film would even look like. Turns out, there was just as much confusion behind the scenes in regard to tackling the project. The Barbie script went through many rewrites—Jenny Bicks wrote the first draft, then Diablo Cody took a crack at it, and then Sony solicited three separate scripts to try to get the project on track. In 2016, it was announced that, after Amy Schumer and her sister, Kim Caramele, did a rewrite on one of those three scripts, Schumer would be starring in the title role … only for her to bow out when faced with creative differences on the film’s direction. Bye, Barbie! Sony made a few more attempts to save the project—Anne Hathaway was briefly attached as a potential lead—but its option on the IP lapsed in 2018, and the film fell to Warner Bros. Margot Robbie was quickly eyed to star, and she eventually brought on Greta Gerwig to write and direct. Hi, Barbie!
Would it have worked? Does it sound like any of this was working? The Barbie production was a trainwreck (no pun intended) from the jump, and it took years for it to fall into the hands of someone who could put together something competent. The premise for the version Schumer was set to helm—“A story about Barbie getting kicked out of Barbie Land for not being perfect enough, landing her in a real world adventure”—sounds similar enough to what Gerwig ended up making, but there was clearly something deeper that was wrong with the script for it to require that many revisions. No matter what the movie would’ve looked like with Schumer or Hathaway as the tiptoed doll, the fact that it ended up with Robbie and Gerwig—and that they were able to pull something together that was as good as Barbie—proves that what we got was the best version possible.
What would be different today? Barbie is marred by bad press and is eventually shunned by critics and audiences alike. Oppenheimer opens unrivaled, and the movie event of summer 2023 is Flashemental (Flelemental?).
