Ah, Tobey Maguire. From the A-list acting (most of the time, at least… we’ll never forget that emo dance) to that perpetual case of babyface, the California native was a staple on the silver screen through the late ’90s and especially the 2000s. Most memorably, he was an inaugural element of the modern superhero era, donning a spandex suit and taking the lead in one of the earliest Marvel "mega successes" in history.
But, though the first years of the new millennium suggested no end to Mr. Maguire’s burgeoning fame, it wasn’t long after the cooler reception to Spider-Man 3 — way back in 2007 — that Maguire’s presence in front of the camera began to become a bit of a rarity. While he still appeared in occasional roles in larger films like The Great Gatsby or that irreverently humorous Satan’s Alley trailer cameo in Tropic Thunder, Maguire just wasn’t up to all that much on the screen. Of course, everything happens for a reason. From personal decisions and negative press to marriage, divorce, and fatherhood, here are some of the reasons Tobey Maguire’s once rising star seems to have sunk below the horizon.
Is Tobey Maguire difficult to work with?
It turns out that, despite his affable appearance, Tobey Maguire may not have always been a treat to work with. When it came to his earlier career, he reportedly had multiple issues with co-stars on various movie sets. James Franco, for example, seems to have held a bit of resentment — reminiscent of Harry Osborn’s struggles — while working alongside his Spider-Man co-star. In an interesting crossing of ways, Franco himself also interviewed actress Charlize Theron who recalled that, when filming Cider House Rules, "Tobey and I had a bit of a rough time, yeah. I mean, we’re good now. It was a difficult movie."
And the drama goes beyond acting circles as well. After the success of the first Spider-Man movie, Maguire tried to get Columbia Pictures to adjust the filming schedule of the second film, allegedly to accommodate his bad back. He even got executives to meet with his neurosurgeon to discuss his workload, only to be dropped from the project a few days later. He was quickly reinstated, partly due to a helping hand from his then-girlfriend’s father, a leading exec at rival studio Universal. But it’s interesting to note that he ended up apologizing for the whole debacle, referring to his own attitude as "inappropriate." Suffice to say, there is a decent amount of evidence pointing to a pattern of being tough to work with.
Tobey Maguire won’t play the popularity game
In an interview with Cinema.com, Tobey Maguire was asked how he felt about comments that he was "too reserved as an actor." His response was rather telling, as he proceeded to explain that he had heard people talking about a "charisma deficit" and that he more or less embraced the fact that he wasn’t a hugely charismatic guy. Basically, he claimed not to equate real-world popularity with doing a good job on set.
Based on his own words and behavior, it would appear that it isn’t in Mr. Maguire’s nature to be excessively flashy, social, or outgoing. That’s pretty impressive, considering the often extroverted characters he’s had to play on screen over the years. But, acting prowess aside, the harsh reality in the dog-eat-dog world of Hollywood is that if you’re not willing to play the popularity game, sooner or later you’re likely to be pushed onto the back burner. And with Maguire’s willing embrace of his own subdued nature, it’s no surprise that his reticent personality has done little to help him as he’s slowly slipped the minds of Hollywood casting agents.
Ending on a low note
Despite launching him to fame, the Spidey flicks may have also had a bit of a negative effect on Tobey Maguire’s career once all was said and done. While the original Spider-Man film was a smash, and the entire trilogy has remained a nostalgic benchmark in Marvel’s cinematic history, the series happened to end on what was pretty universally considered the worst of the three. The project had a lot of factors stacked against it, and even director Sam Raimi was disenchanted with the final product.
Shortly after the sour critical and fan response, talks between Raimi and Sony about a fourth installment fell through. Regardless of whatever complex negotiations may have happened behind the scenes, it was hard for audiences not to lay blame for the cancellation squarely at the feet of Spider-Man 3. Needless to say, ending your tenure as an iconic character with a movie so unpopular it seemingly kills a franchise tends to undo some of the goodwill of a strong beginning. It’s no surprise that the whole scenario took a bit of the luster off of the "Marvel star power" that initially did so much to fuel Maguire’s career.
Tobey Maguire’s marriage, a divorce, and fatherhood
It may seem cliché, but that doesn’t change the fact that marriage and parenting can be tough challenges that take all the time we can throw at them. It should come as no surprise, then, that Tobey Maguire’s marriage to Jennifer Meyer in 2007 also happened to coincide with the beginning of his gradual fade from the limelight. The relationship endured for nine years before they announced that they were officially separating in October 2016. According to Entertainment Tonight, by that point, their marriage had slowly been crumbling "over the course of time." In an additional statement, the couple told People Magazine that "After much soul searching and consideration we have made the decision to separate as a couple." The divorce was finalized a year later.
Fortunately, though, the split was amicable, and their commitment to the family they had started together hadn’t been lost in the shuffle. They still remained the dedicated parents of two children, Ruby and Otis, adding to their statement that "as devoted parents, our first priority remains raising our children together with enduring love, respect and friendship." And this sentiment hasn’t waned over time, either. Us Weekly reported that Meyer considers her ex-husband her best friend, and the two have continued to strive to raise happy children despite the circumstances.
He may not play the popularity game, but Tobey Maguire has certainly shown a penchant for entertainment of a different sort: gambling. And we’re not talking about a filthy rich celebrity having some fun. Maguire has established a reputation over the years as a winner. As far back as 2011, CNN reported that Mr. Maguire had to settle a lawsuit to prevent having to pay back the princely sum of $311,000 that he had won a few years earlier. The problem? The money had been stolen from investors by an illegal Ponzi scheme. While all Maguire did was accidentally win the money by playing some darn good poker, being in the headlines because you’re connected with stolen cash isn’t quite the same kind of popularity one gets from playing a beloved childhood superhero.
But Maguire’s gambling issues went deeper than simply winning stolen money. They were put on much more damning display through the book and movie adaptation Molly’s Game, which followed the real-life story of Molly Bloom as she organized underground poker games for a host of rich players, including one "Player X." The unnamed gambler, who happens to be a jerk of the highest variety that enjoyed "destroying the lives of his fellow players" can be quite easily connected to none other than Maguire. From winning stolen money to his overall sinister reputation as a player, Maguire’s gambling has hardly done his reputation any favors.
Tobey Maguire’s journey from actor to producer
When he’s not gambling or tending to his kids, Tobey Maguire is still first and foremost an entertainer. But while earlier in his career that primarily meant acting, recently Maguire has begun to spin off more and more in a different direction as a producer. It’s not uncommon for a popular actor to attempt to leverage their successful career in front of the camera into one behind it. It started with big shots like Charlie Chaplin and has continued right through to modern legends like Clint Eastwood, John Krasinski, and now Tobey Maguire.
Interestingly, it’s through this shift that Maguire seems to have found the ideal way to truly express his passions. Again, the man isn’t an attention hog. He doesn’t love the paparazzi, he’s known for being terse in his responses to fans, and he’s openly expressed the struggle he has with overcoming his introverted personality in order to take on larger-than-life characters on the silver screen. So it’s only natural that when his fame and fortune reached a certain point, Maguire attempted to move out of the spotlight without dropping his passion for cinema altogether.
Tobey Maguire’s production career got off to a slow start
On paper, Tobey Maguire’s shift to producing films seems to have panned out pretty well as far as quantity of content is concerned. The ex-superhero managed to produce a decent number of movies over time, although the truth is that his production prowess initially fell a bit short of the mark, especially if you grade him against the curve of other A-list actor-turned-producers.
Nevertheless, Maguire has managed to stamp his name on several movies that found at least minor success, including the musical comedy-drama Rock of Ages, the slow-moving but tense Cold War thriller Pawn Sacrifice — which Maguire starred in — and the alien-infested action-drama The 5th Wave. Maguire stayed busy helping to produce these films for several years as the early 2010s unfolded. He also established his own production company in 2012, called Material Pictures, which helped to co-produce all of the aforementioned films.
While most of the fledgling producer’s earlier projects were decently produced, they were decidedly not box office successes and hardly the kind of material that can help vault an ambitious entertainer back into the limelight.
Tobey Maguire’s a little bit picky
Another factor that has chilled the relationship between Hollywood and Tobey Maguire is the fact that he doesn’t accept just any old acting job that’s offered to him these days. He’s been very selective about the roles he’s taken on in the years since the Spider-Man films, with only four of those landing him on the big screen during that time. In an interview with Nylon back in 2015, Maguire explained that "it’s always difficult to find projects that I want to get involved in, so that’s a continuous challenge."
He went on to say that his choosy nature stems from the fact that an acting/producing career involves a lot of commitment and investment. If he’s not deeply interested in the story of the project, it becomes very hard for him to enjoy the experience. And we can’t argue with that. At this point in his career, if he can’t do what he loves then he might as well pack up shop.
An almost cameo as Spider-Man
Okay, Tobey Maguire didn’t actually come all that close to actually returning to the big screen as a superhero — at least as far as we can tell. However, it’s worth noting that the idea was genuinely in the cards at one point, and we’re not just talking about a half-brained fan theory, either. It comes straight from the mouth of one of the producers for Sony’s Spider-Man: Into the Spider-Verse.
During a watch party in early May 2020, Christopher Miller revealed that "We pitched the Sony brass an ambitious tag involving Spider-Ham, Tobey, Andrew, and Tom. They felt it was ‘too soon.’"
Into the Spider-Verse was already jam-packed with pleasant multi-dimensional surprises, but the fact that there were actual plans in development to involve the three live-action members of the Sony Spider-Man Universe of Characters is exciting even just to think about. Couple it up with J.K. Simmons’ cameo as J. Jonah Jameson in Spider-Man: Far from Home and a decent case could have been made for a real push to get Maguire out of superhero retirement in order to reprise his role on multiple occasions. But alas, it appears the chances of this happening remain a long shot.
Could Tobey Maguire return to the superhero world?
Interestingly enough, a quick cameo in Into the Spider-Verse wasn’t Tobey Maguire’s only potential lifeline to his superhero past. In a 2019 interview with the Hollywood Reporter, Maguire was asked if he would ever don a superhero suit again, to which he gave the nebulous response, "I just don’t really have an ‘I would or wouldn’t do’ mindset. I’ll just do whatever… Whatever it is that comes that I feel called to, that may or may not fit in any kind of box."
This is hardly the sentiment of an ambitious actor looking to get back into mainstream superhero flicks, and it should also be weighed against his historically picky attitude when it comes to the roles that he’ll accept. However, it also is definitively not a denial of future cinematic heroics. In fact, Maguire’s apparently laissez-faire "I would or wouldn’t do" mindset seems to leave the door wide open for a return if a studio manages to woo him in just the right way. It’s something that the modern crossover-happy, multiverse-minded superhero universes could certainly look to capitalize on in the future.
Tobey Maguire, competitive puzzler
There are plenty of new professional projects and important life events keeping Tobey Maguire out of Hollywood, but there are also a few non-film hobbies that he’s admitted to investing time in. While the fact that the ex-Hollywood regular engages in personal activities is hardly surprising, the activities themselves are anything but predictable.
When asked what he does in his downtime, Maguire headlined his list of leisure pursuits with playing pickle ball with his friends. He followed up this rather interesting revelation by listing off hanging out with his kids and going skiing, both pretty normal ways to spend your spare time.
Then he casually added one more item to the list: competitive puzzling. That’s right, Peter Parker Maguire spends significant portions of his spare time putting puzzles together at a rapacious rate. While the thought of putting together a jigsaw puzzle or two from time to time makes sense, it only seems natural that Maguire would feel the need to take this seemingly pointless activity to the next level.
Tobey Maguire’s move into independent cinema
Tobey Maguire’s shift from before to behind the camera might have initially looked like the type of dabbling many actors do when they reach a certain level of success. But over the years, Maguire has managed to find an increasing level of success as a producer.
Material Pictures gave Maguire an opportunity to break away from acting while simultaneously maintaining his passion for the entertainment industry. Untethered from concerns for his on-camera career, Maguire began to focus more intently on behind-the-scenes work, and his new production company slowly started to gain some traction. By 2019, the studio, which produced three films that year, finally found noteworthy success.
One of the films, Boyz in the Wood, won the Midnighters Audience Award at SXSW, while another, Brittany Runs a Marathon, was purchased by Amazon for an impressive $14 million and went on to earn considerable critical acclaim. With success finally materializing for Material, the chances of Maguire stepping back into the Hollywood limelight seem to grow slimmer with each passing year.
What does the future hold for Tobey Maguire?
Tobey Maguire last found his way in front of a camera way back in 2014. His voice is heard alongside Alec Baldwin’s in DreamWorks’ 2017 animated hit The Boss Baby, but apart from that, he’s remained hidden behind the camera. When asked by the Hollywood Reporter if he was retired from acting, though, Maguire once again gave a hazy answer, declaring, "I’ll do what I feel called to do. I suspect I’ll be excited when I do it. Like, just whenever the calling appears, I guess." While Maguire may not consider his acting career dead in the water, the truth is, he may have a bit of a long road ahead of him if he ever wants to start landing larger jobs in Hollywood again.
The question that really needs to be asked is whether Maguire wants that in the first place. Clearly, since he hung up his Spidey-suit, he seems to have his hands pretty full simply being a father and producing movies with an occasional cameo or supporting role added in. Perhaps we’ll see the ex-superhero hit the big leagues again one day, but that seems to be a possibility that depends as much on Mr. Maguire’s wishes as it does on anything else.