The Great Maguire

It’s Tobey Maguire Old Sport!


After a rough childhood, Tobey Maguire catapulted himself out of the gritty streets of Hollywood and into the Hollywood of myth. An expert poker player and self-improvement junkie, he has outgrown the Spider-Man franchise (which brought in more than $2.4 billion) and now finds himself determined to win the game as a star of “The Great Gatsby” and head of his own production company.

For M’s spring cover feature, senior consulting editor Jim Windolf profiled the actor in the midst of a professional reboot.

Photo by Matthew Brookes

The Great Gatsby begins with Nick Carraway, a poetic bond trader, recalling some advice from his father: “Whenever you feel like criticizing anyone, just remember that all the people in this world haven’t had the advantages you’ve had.”

Tobey Maguire, who plays Carraway in Baz Luhrmann’s upcoming movie version of F. Scott’s Fitzgerald’s 1925 classic, has a lot in common with the character—a finely tuned social radar, a contemplative streak, and a sense of moral purpose. But the piece of advice delivered by Mr. Carraway to the young Nick is not something he was ever really in need of hearing. Unlike the Gatsby narrator, not to mention his Princeton-educated creator, Maguire is not someone who grew up in a comfortable home with all the niceties in place. He is, instead, one of the people who, in Fitzgeraldian terms, should not be judged too quickly.


Last decade, the combination of the Spider-Man character and Maguire’s soulfulness matched up beautifully with the cultural moment. Over the course of the three Spider-Man movies directed by Sam Raimi, which hit more than $2.4 billion at box offices worldwide, the spectacle of a sweet, brainy kid taking the fight to those who sought to destroy a comic-book New York, so soon after the real New York had been attacked, gave American audiences a safe place tograpple with their conflicting desires to keep the old virtues intact even as they thirsted for revenge.

Maguire wasn’t Sylvester Stallone, he wasn’t Arnold Schwarzenegger, he wasn’t even Tom Cruise. His naturalistic acting style, real as can be, freshened the operatic superhero genre and would end up being used, to even more profitable effect, by Robert Downey, Jr. (Iron Man) and Mark Ruffalo (the Hulk) in later Marvel movies.

Maguire’s moonbeam eyes, moreover, suggested something virtuous we feared we might have lost along the way—but he still managed to rescue a battered New York and to deliver a nice ass-kicking to those who tried to crush it. He was a Frank Capra hero in a CGI world, a good man in a political climate complicated by waterboarding, drone strikes, and Guantanamo. It was an appealing Hollywood dream.

Now, at 37, this man, who played teenagers deep into his twenties, is a husband, father, and budding executive, whose Material Pictures production company is housed on the Sony Pictures Entertainment campus in Los Angeles.

On a recent morning he was laughing in his office during a meeting with the Haas twins—Simon and Nikolai Haas, to be exact. They are the younger brothers to Maguire’s longtime friend actor Lukas Haas. Lately featured in Wallpaper magazine, the Haas boys are lanky designer-builders with tattoos and workman’s hands. They built most of the furniture in this place, to Maguire’s specifications. Today they were discussing the new work space Maguire is planning to build away from the Sony lot as part of what seems to be a personal and professional overhaul.

A figurine by KAWS and other pieces he has collected, by Edward Ruscha and Kaz Oshiro, lent some charm to the raw rooms. Hanging in Maguire’s personal office were two whiteboards filled with French phrases neatly handwritten in marker, so that he could learn bits of the language with glances from his desk. Against the far wall was another sign of his autodidacticism: a small piano, with an open book of beginner’s sheet music on the stand.

Maguire sat down. He was wearing a clean white T-shirt with sleeves short enough to expose his thick biceps. He is an eye-contact guy. When he’s on-screen, his eyes do much of the work. Sometimes they are serene, sometimes they are charged with the emotional ammo he stored away through a difficult childhood and wild teen years.

I asked him about the acting he did when he was a kid, even before he was cast on the short-lived 1992 Fox sitcom “Great Scott!”

“I remember I auditioned for this thing when I was 14 called ‘Tales From the Whoop,’” he said. “I think it was on HBO, with Whoopi Goldberg. I hadn’t done anything. Maybe a commercial or two and a student film. The director brought me in, and it was between me and another kid who was on a very popular TV show. He’d been on it for years, and everybody was very comfortable with him doing the part. And the audition was like ten blocks from my house. I lived in Hollywood, and I think I had walked. So I auditioned, and the director was explaining that he liked me, and I got the feeling he wanted to hire me, but his more conservative side and the other people involved were saying they should hire the other person. And before I left the room, I stopped. And I turned to him and said, ‘You know what? Sometimes it’s good to take a risk.’ Then I walked out the door. And I ran home, and I knew I had gotten the job.”

“When you got home that day, what was the apartment like?”

He gave a laugh that suggested embarrassment. “What was the apartment like?” he said, repeating the question, as if stalling for time.

He was seated not very far, in terms of physical distance, from where he had lived as a kid; but here on the Sony lot, he was worlds away from all that. It struck me that not everyone who escapes bad circumstances feels the need to trumpet his or her past. Uncommonly, in a city built on extroverts, the affable but guarded Maguire is not a big participant in the blabby culture that provides grist for talk shows, powers tell-all memoirs up bestseller lists, and pervades our online lives.

So maybe he is a little less like Nick Carraway, who transforms what he sees into shapely narratives rounded off with aphorisms, and a little more like Jay Gatsby himself, who lives theatrically, with one eye fixed on a secret notion of success and who camouflages his dirt-scrap origins (as James Gatz of North Dakota) in the trappings of an immense wealth made vivid, in his case, through all-night parties, a yellow car, and all those beautiful shirts.

“That place,” Maguire continued at last, speaking of the long-ago Hollywood apartment, “was with my mom. I lived in a lot of different places, in a lot of different configurations, but I lived there for a couple years. It was a small one-bedroom place.”

“Did you get along with your mom in those days?”

Deep breath. Reluctant answer. “Sometimes yes, sometimes no.”

He was born in Santa Monica in 1975. His parents, young and poor, split up before he was three. He switched schools more times than he can count. Mostly he stayed in California with his mother, but sometimes he found himself with his father or other family members in Oregon or Washington.

“I didn’t belong anywhere,” Maguire said. “I certainly had the ability of a good observer. If I went to a school, I could figure out who was who, who belonged to what group, and I could find my way in. Like Nick Carraway, in a sense, I could listen to people, and I was pretty sensitive, and then I also had a toughness to me, because that’s what happens. I moved around a ton. I loved school and I was a good student, but the social anxiety finally got to me, sort of overwhelmed me, in just searching for a place to belong or a place to fit. Acting became that for me. I hooked up with the rest of the folks out there like me.”

“Did you quit school altogether?”

“Ninth grade was the last grade where I went to school at all, but I really consider myself only completing sixth grade.”

“Were you doing drugs and stuff like that?”

“I started drinking and doing some drugs when I was 14. Very little at that time. When I was 16, 17, I started doing a lot more drugs. Mostly I smoked weed, though I experimented—a lot of different things. Fortunately, I got sober when I was 19.”

By that time, in possession of a confidence that bordered on arrogance, he decided he needed a publicist. He interviewed seven people for the job. The winner, Kelly Bush, still represents him today. “I know this is a little obnoxious,” he said, “but I was a little obnoxious. I was 19 and I said to her, ‘Listen.’ I don’t know if I said ‘I am going to be extremely successful’ or ‘I am going to be a major movie star,’ but it was something along those lines. I had no doubt. In fact, it was a slower time line than I expected.”

“What was it like when you had money for the first time?”

“I remember making money when I did, like, two lines on ‘Blossom’ or ‘Roseanne.’ I was getting checks and going, ‘Holy shit!’ I became a contributor to the household income, because we didn’t have much money. When I was 17, I did 13 episodes of a TV show [‘Great Scott!’], so I made a little money in that period of time. I really wanted to stretch my money as far as possible and sock away as much as I could. I think it finally ran out after two years.” He is still careful with it. “I have one home,” he said. “I don’t have three houses and a bunch of unnecessary staff, and I don’t go party. I make investments. I try to make things have a purpose. It’s part of a larger structure of what I am trying to accomplish.”

Paradoxically, though, he likes to lay his money on the line at the poker table. It seems a dangerous flirtation with chance for someone who knows what it is like to have nothing, but he is coolheaded enough, cocky enough, to keep at it.

With his appearances on the tournament circuit last decade, and his participation in other, more discreet games in private homes and hotel suites, he is perhaps the most renowned Hollywood card sharp since Zeppo Marx. Poker pro Daniel Negreanu assessed Maguire’s game in a recent interview with the Web site Hollywood, Interrupted: “He has the ability to fake weakness or strength, which is definitely an asset when you play poker.” During a television broadcast, 13-time World Series of Poker champion Phil Hellmuth estimated that Maguire has scored more than $10 million in poker winnings. The actor took first place (and $95,480) in the 2004 No Limits Texas Hold ’Em Invitational. Again going up against professionals in the 2007 World Series of Poker Main Event, he finished 292nd and grabbed $40,000.

These days he doesn’t go in for tournament play. “It’s way too time-consuming,” he said. “The big tournaments, like the World Series of Poker, to sit around for nine days and play poker, I just don’t have those days. I like my kids too much.”

I asked him what, exactly, he liked about the game.

“There is definitely a kind of intellectual and psychological sparring that’s partly what I enjoy about it, as well as the camaraderie,” Maguire said. “You’re measuring math against people’s tendencies.” He described his thought process at the poker table: “How has the recent history affected what your tendencies are? And how much are you thinking about what I’m thinking about? And how will that affect what you do? And are you the type of player who considers that, or not? I’m
doing that with seven people at the same time, and it’s engaging and fun.”

It sounds like good training for navigating L.A.’s executive wings.

Now he has a house on a Brentwood acre; a beautiful wife, Jennifer Meyer Maguire, who is a jewelry designer and the daughter of Universal Studios president and chief operating officer Ron Meyer; and two children, Ruby and Otis, ages six and three. By any measure, he is having a successful career, which he has achieved with a little luck but mainly through his own careful assessment of his strengths and his diligent application of them.

Still, he seems restless. Beneath the placid surface much commented on by film critics, who tend to love his work, lies a bristling ambition, a monkish sense of discipline (he’s a vegan who doesn’t smoke, doesn’t drink), and an instinct to hold himself somewhat aloof from the pleasure rounds of the L.A. scene (aside from the poker games and a front-row seat at the occasional Lakers game).

“Whenever he decides to do something, he’ll stop at nothing,” Jennifer Meyer Maguire said over the phone. She met him roughly 17 years ago. “I must have been 20 years old,” she said. “There was this store on Sunset, Tracey Ross, and it was the beginning of those really cool stores. He and his friends used to sit and play backgammon and watch all the pretty girls come through. I would see him over the years, and we ended up hanging out. He knew how to woo a girl. From the day we kissed, we’ve never broken up or had any sort of break. We got married five years ago and we’ve been together ten. We’re really close with my family, and Tobey has the most amazing friends.”

One of Maguire’s closest pals, going back to the start of his career, is Leonardo DiCaprio, who plays Gatsby in the new movie. Maguire’s wife and children lived with the cast and crew during the six-month shoot in director Baz Luhrmann’s home city of Sydney, where filming is cheaper than it is in L.A. Jennifer Meyer Maguire reports that her children call DiCaprio “Uncle Leo.” “He’s part of our family,” she added.

Concerning her husband’s rough upbringing, which he seems reluctant to discuss in detail, she said, “You know what? It would bring tears to your eyes, if you could hear all his childhood stories and hear how incredible it is, from where he came.” As for his Timothy Ferriss–like habit of making himself the subject of a never-ending personal-growth experiment, she said, “Now there’s a drum set being put together in my house, because he wants to learn how to play the drums. He’s all about self-improvement on a lot of levels.”

He made his reputation with a series of prestige films: Ang Lee’s “The Ice Storm,” Gary Ross’ “Pleasantville,” Lasse Hallström’s “The Cider House Rules,” and Curtis Hanson’s “Wonder Boys.” In the wake of the best-reviewed installment in his superhero trilogy, “Spider-Man 2,” Maguire earned $32 million in a single year, according to Forbes. InStyle named him “Sexiest Big Screen Action Hero” of 2002. That same year, Barbara Walters enlisted him for her annual “10 Most Fascinating People” special, and he came through with a rare on-camera childhood confession, telling the host, “Me and my mom would go into a grocery store and get groceries and pay for them with food stamps, and I would run out of the store, embarrassed.”

Maguire slimmed way down for “Seabiscuit” (seven Oscar nominations) and put on muscle once again for “Spider-Man 3” ($890 million in worldwide box office). Before the fourth installment was under way, Sony decided to blow it up and go with a new actor, a new director—a new Spider-Man for a new decade. Maguire graciously interviewed his successor, Andrew Garfield, for V magazine in what amounted to a formal handoff of the skintight blue and red jumpsuit.

And so he found himself left to navigate the next phase of his career without the protection of a big-budget franchise. He got nice reviews and a Golden Globe nomination for his role as a returning war veteran with post-traumatic stress disorder in “Brothers,” and went on to play the lead in a dark comedy, “The Details.” But he was replaced (by Rafe Spall) in Ang Lee’s “Life of Pi” after shooting scenes that had him in the framing-device role of the writer character. “I love Tobey,” Lee told USA Today. “But it’s a small part. So when it’s a movie star sitting there, it captures attention. It didn’t really work out.”

Now things are in flux as Maguire hatches a new plan for himself while hoping to defy that depressing Fitzgerald maxim “There are no second acts in American lives.” He has switched agents, leaving Creative Artists Agency for William Morris Endeavor. He has also ramped up Material Pictures, which has several dozen properties in various stages of development (a mix of small movies, “Transformers”-size projects, television shows, and documentaries). The work is overseen, in part, by Matthew Plouffe, the former director of production at Focus Features. Maguire said his company’s first-look deal with Sony has come to an end, which means that Material Pictures is an independent.

And so here he is, in need of a hit and depending on the idiosyncratic Luhrmann to pull off the latest Hollywood attempt to make cinematic sense of The Great Gatsby, a Jazz Age tale to which the director has lent a contemporary touch in the form of a hip-hop soundtrack and Jay-Z score.

He met Luhrmann while auditioning for Romeo + Juliet, which helped make his pal DiCaprio a star in 1996. Maguire was aiming to play Romeo’s cousin, Benvolio Montague. “Romeo was always meant for Leo,” he said. He didn’t get the part. This was something that happened more than once in those days. Leo was on a fast upward trajectory; Tobey plodded to the top.

The two of them had met during NBC’s 1990–91 incarnation of the Ron Howard movie “Parenthood.” “It was a Halloween episode,” Maguire recalled. “We were punk kids. We toilet-papered houses.” Not long afterward they were up for the role of the son in This Boy’s Life, the 1993 adaptation (starring Robert De Niro) of the Tobias Wolff memoir. “We were auditioning with De Niro, and in the fourth round of callbacks, we said to each other, ‘If either one of us gets this part, we’ll help the other get a part,’ and that’s what happened.” DiCaprio won out; Maguire got the consolation prize of a small role.

The Great Gatsby is the first movie they have appeared in together since then. But probably more important to Maguire’s future is whether or not he can wring some box-office success out of the projects he has in development at Material Pictures.

He said his company will make two or three movies this year, if things break right. The first, shooting as early as this summer, is likely to be “Pawn Sacrifice,” a story centered on Bobby Fischer’s Cold War duel against fellow grandmaster Boris Spassky of the U.S.S.R. The director is Edward Zwick, who has made films ranging from the Oscar-winning “Glory” in 1989 to the $100-million-plus-earning “Love and Other Drugs” in 2010. Maguire will play Fischer, a genius known for his difficult personality. The tortured egghead is a type much loved by the Academy—see Russell Crowe in “A Beautiful Mind”—and the fact that Fischer was, like Maguire, an intense gamer with laser focus makes for an ideal match of actor and character; but he said he is not using his production house as a way for him to snag choice roles.

“Sometimes I imagine being on a hillside where there are different camps of people, right?” Maguire said, going dreamy. “There are hunters and basket-weavers and storytellers. And I’m sitting in the circle of storytellers. That’s what I do. Our job is to help contextualize the human experience. And I can express that through my acting, I can express that through collaborating with other storytellers and building stories, or those two things can coincide.”

On the packed bookshelves I noticed Uta Hagen’s “Respect for Acting,” Karen Armstrong’s “A History of God,” Baratunde Thurston’s “How to Be Black,” Mihaly Csikszentmihalyi’s “Flow: The Psychology of Optimal Experience,” and what appeared to be a couple of pristine first editions of “The Great Gatsby.”

At the end of the novel, following the (spoiler!) swimming-pool murder of Gatsby, Fitzgerald seems to liken his tragic hero’s airy notions of success to the enchanted dreams of the Dutch sailors who approached the “fresh, green breast of the new world” in the days before industrialization had turned it into a land of snarled roads, gaudy billboards (Dr. T.J. Eckleburg!), and ash heaps. Gatsby takes the fall for all of us suckers, and that may be why the book still has resonance and has tempted movie directors going all the way back to Herbert Brenon in the silent era.

But for all Maguire has in common with Carraway, whose melancholy and honesty (“I am one of the few honest people that I have ever met,” he says at one point in the narrative) inform the work as a whole, he cannot accept the bleakness of the novel’s ending.

It may be true that we are all reaching for something we cannot have, that our striving for some lost Eden will prove a botch—but Maguire is having none of it. He is more akin to those all-American go-getters such as Dale Carnegie and Norman Vincent Peale than to Fitzgerald, who ended his days, at 44, broken and drunk, in Hollywood. With his veganism, his teetotaling, his workouts, his French, his piano, his drums, his constant reading—with his overall design—Maguire is cut from a different cloth. The final lines of The Great Gatsby are sadly persuasive, but living with them would drive anyone to a crack-up.

“I believe in progress,” Maguire said. “It’s interesting—those last pages and the very last lines are interesting, you know? I kept digging around, and I found it fascinating. But I’m an optimistic person. I’ve always been optimistic about succeeding.”

By now Maguire has been through something and emerged intact. He has starred in blockbusters and has been cut from a big Oscar-nominated film. But even after having experienced the successes that leave some people sated and the disappointments that make others hesitant, he is holding onto the pluckiness, the drive, that catapulted him out of the actual, grim Hollywood of his childhood and into the Hollywood of myth. He remains more like the young Jimmy Gatz of North Dakota, who made careful lists of what he had to accomplish each day (“Rise from bed… Dumbbell exercise and wall-scaling… Study electricity, etc…. Work…”), than the pink-suited Gatsby of New York, whose elaborate preparations end in a crash.

Recent years have dealt Maguire a certain hand. Now he is checking his cards and looking ahead to the next play. He is considering what others in the game may or may not do. If it works out the way he hopes, the way he believes—jackpot.



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