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Tobey Maguire Was the Original — and Best — Spider-Man

The latest installment of Misleading Men, the series where we look back at actors who ruled Hollywood for one brief shining moment

Last week, Tobey Maguire turned 42. That seems impossible. In the mind’s eye, he’s perpetually youthful, expertly playing coming-of-age characters always on the cusp of manhood. A few years ago, The Guardian talked to him about his eternally boyish looks. “I don’t even know how old I look any more,” he confessed. “I did look very young. I see kids driving and think, ‘Oh God, they look 12.’ I was one of those. But I seem to get consideration for characters my age these days.”

That may be the case, but as another Spider-Man reboot approaches, there remains little doubt that he’s still the definitive Peter Parker, the most famous teenage superhero of them all — even if Maguire was 26 when Spider-Man hit theaters in the summer of 2002. The role was the culmination of everything he’d made up to that point. Since then, he’s watched Hollywood try to recapture the Spider-Man magic he conjured effortlessly.

Born in Santa Monica, Maguire was raised by very young parents — 18 and 20 — who split up when he was 3. “They were just babies, doing whatever the heck they thought they should be doing,” he recalled in 2007.

“As a kid, I was very poor,” he later told The Guardian. “I mean, it’s all relative, but we would get groceries from neighbors. I always had a roof over my head, but I slept on couches of relatives, and some nights we wandered into a shelter. My family had food stamps and government medical insurance. And I wanted to get out of that, so my ambition was initially to make money; I was pretty driven.”

After abandoning the idea of becoming a chef, Maguire took to acting, landing commercials for Doritos and Atari and booking one-off roles on Roseanne and Blossom. He was the prototypical cute kid: handsome, energetic and with a little sass to him.

After starring in the short-lived 1992 sitcom Great Scott!, he snagged a part in This Boy’s Life, also the first major big-screen role for future Oscar-winner Leonardo DiCaprio. The two had become close friends in the early 1990s, often auditioning for the same roles. As DiCaprio became more and more successful, he tried his best to help his buddy by convincing producers to cast him, too. Consequently, almost 30 years later, they remain connected in the public’s consciousness as part of a gang of Hollywood pals who were infamously known back then as the Pussy Posse.

“We’re both really competitive people,” Maguire said in 2013 about his long friendship with DiCaprio. “I think we have a lot of confidence in our own individual paths, so whether it’s with each other, or other friends of ours, we root for them. We’re fans of our greatest competitors. We can joke with each other about competition, but are supportive. I have a whole bunch of friends like that. I’m glad that’s the culture of my group.”

But it was also a period when the partying took its toll — years later, he acknowledged that he’d sought treatment for alcoholism and revealed that Alcoholics Anonymous had helped him get sober. “It’s just all practical,” he said in 2003 of AA. “There are no holes in the program. It’s so, so simple. I come in, I ask for help. It has totally changed my life.”

Onscreen, though, he was developing the persona of a clean-cut kid coming face-to-face with the outside world’s harsh realities (usually for the first time). In 1997’s The Ice Storm, he played a dweeby teen who’s smitten with a more outgoing girl at his boarding school. The following year, he starred in Pleasantville, where he portrayed a sweet, shy teen who gets transported into the world of his favorite 1950s sitcom, finding himself right at home in its modest, conservative outlook. And in The Cider House Rules and Wonder Boys, it was more of the same — he was the affable young man in the ensemble, the symbol of virtue or innocence.

Maybe he was guilty of playing a type, but for a young actor, he was impeccable at selecting good roles in top-flight films with top-flight directors. Asked in 2003 what his secret was, Maguire responded, “I wait. I don’t want to work as an actor just because I haven’t worked in six months. I want to only do things when I really want to do them, and if they only come along every year, year and a half, then that’s fine.”

The only thing that was really missing were leading-man roles. That changed when he decided to throw his hat into the ring for a long-in-the-works big-screen adaptation of Spider-Man. Other actors, including James Franco, also were considered for Peter Parker, but Maguire walked away with the role.

The jump to superhero might have seemed like a stretch, but Maguire understood the connective tissue between his earlier roles and Parker’s outsider status as a hopeless nerd who just so happens to get bitten by a radioactive spider. “He’s one of us,” Maguire explained to CNN in 2002. “He’s someone kids can relate to, and he doesn’t die out, so a new generation can come along and appreciate him. He’s a relatable, everyday kid. He’s not an alien or a multimillionaire. We can imagine ourselves in his position.”

The decision to play Spider-Man was partly a pragmatic one — as Maguire put it at the time, he wanted to “open up more doors” — but when the first film opened May 3, 2002, there was no guarantee it would be a commercial colossus. These days, superhero movies hit theaters once a month. Back then, though, the Batman franchise had run out of gas thanks to Joel Schumacher’s campy installments; there hadn’t been a Superman film in 15 years; and X-Men movies were the only Marvel properties on the big screen. But with the help of Evil Dead director Sam Raimi and onscreen love interest Kirsten Dunst, a fellow indie actor, Spider-Man was the year’s biggest hit, paving the way for two sequels and helping kick-start the current comic-book-movie craze.

The trick was Maguire’s utter believability as Parker, who was another sweet, awkward high school kid that the actor personalized with his boyish enthusiasm, which made his superhero alter ego immensely likable. For once, the clean-cut kid helped save the world from evildoers — and got the girl in the process.

But after 2007’s Spider-Man 3, it was time for Maguire to grow up on-screen. As he told Time in 2003 when he signed up to play a jockey in the true-life drama Seabiscuit, “There probably won’t be a lot more things I do where the character is, like, a virginal, innocent, sexually naive kind of guy.”

And while he’s accomplished a more mature film presence, his choices haven’t necessarily been as strong as his pre-Spidey days. The remake of Brothers (for which Maguire received a Golden Globe nomination) was passable enough, and he was appreciably melancholy as Nick Carraway in the gonzo 2013 adaptation of The Great Gatsby — although it was perhaps a little too meta that his character looked up to the worldly, dashing Jay Gatsby, played by his old pal DiCaprio. But he’s yet to find a signature role that defines this new adult era.

Oddly, what’s bolstered Maguire’s legacy most since 2007 has been Sony’s attempts to resuscitate the Spider-Man franchise in his absence, with mixed results. In 2012, the studio released The Amazing Spider-Man, casting another distinguished actor, Andrew Garfield, to play Parker. It was a worthy effort, but neither The Amazing Spider-Man nor the 2014 follow-up could escape the shadow of the original trilogy.

Now with Spider-Man: Homecoming, 21-year-old Tom Holland has taken over the reigns. And yet, the cast and crew are really just chasing what Maguire achieved 15 years ago with the character.

Holland has made it clear to journalists that it was Maguire’s interpretation of the character that stuck with him, saying, “He was my role model growing up. He was my favorite character. So I had to keep reminding myself that I was going to have that same impact on kids, and a generation. I really wanted to do them proud, and to be a solid role model for them, and also make a young, fresh version of a character that we know and love so well.”

This was all different back in the early 2000s when Maguire took on the role. At the time, there really was no definitive version of Peter Parker, so Maguire was able to imbue the character with his own essence. Any actor who comes on board now, however, has to combat what Maguire achieved — they basically have to out-Tobey the master.

All of which brings up a funny fact about the way Hollywood works: Sony wants to recapture the younger Maguire, while the real Maguire is out there learning how to move on from that version of himself.