Tobey Maguirehas had a long and prolific career as an actor. Since his debut film in 1989,The Wizard— in which the fourteen-year-old amateur actor played the role of a villain gooney — Maguire has gone on to make over 40 films.

Yes, Maguire has beenin all kinds of movies. While he is most famous for being the original Peter Parker, a role he has reintroduced to the world to fall in love with all over again in 2022’sSpider-Man: No Way Home, Maguire has been a part of lots of different kinds of projects. He’s been a part of D-list movies and award-winning films. He’s been a part of coming-of-age stories, biopics, dramas, comedies, fantasies, mysteries, Westerns, and thrillers. Maguire’s reputation has built him a loyal fan base that views Maguire’s films as a part of a series of classics that have to be watched simply because he’s a part of them. After all, when you hear about a Tobey Maguire movie, you’re immediately curious.

Pleasantville

And yet, with such a long line of projects under his belt, there is one film where Tobey Maguire shines the most.

Welcome to Pleasantville

In 1998, New Line Cinema released a teenage comedy with a unique plot. Accustomed to using television as a way to escape the pain and suffering of their own lives, two teenagers must figure out how to get back to their own reality after they get stuck in a 1950s sitcom. You may remember watching this little title directed by Gary Ross (known for other films such asThe Hunger Games, Seabiscuit, andOcean’s 8)on cable television when you were growing up, or perhaps this is the first time you’ve heard aboutPleasantville. Regardless, the film is a hidden gem that offers a great narrative supported by unique color and composition and, of course, stellar acting from the leads, Tobey Maguire and Reese Witherspoon.

Related:How Pleasantville Exposes the Problem With Nostalgia (and Inspired WandaVision)

David and his sister live very different lives. Jennifer, a shallow girl who is used to having attention and popularity in her life at school, is the perfect foil to David, a shy loner who spends most of his time watching the 1950s black-and-white classicPleasantville. When the two siblings fight over control of the TV remote one night, a mysterious technician arrives and hands over a new remote control. Suddenly, David and Jennifer’s lives are turned upside down. The two are magically transported into the world of Pleasantville, where they take on the roles of Bud and Mary Sue Parker — forced to keep up the show’s plot for fear of what disastrous consequences happen if they do not.

From there,Pleasantvilleis a movie about self-discovery and interpersonal relationships, as well as a meta-commentary on the United States' obsessionwith the suburban fairytaleand staying within the confines of what society dictates. David and Jennifer must learn more about themselves as they play their characters and must work together to figure out how to get back to the real world. The film was positively received by critics and audiences alike for its unique plot, important messaging, and most of all its light-hearted humor.

Tobey Maguire Loses His Powers in Spider-Man 2

Wait, Not Spiderman?

If you are reading this, you may be thinking; “Wait a second. Of course, Tobey Maguire’s best filmhasto be Spider-Man?" Yes, McGuire certainly shines as Sony’s first rendition of Peter Parker. For most, Maguire perfectly captures the Peter Parker they came to love in the original Marvel Comics. Audiences feel an intense kinship with Maguire’s Peter Parker for his ability to embody what it feels like to be a loser in high school. This is because, unlike Andrew Garfield and Tom Holland, Maguire looks and feels like a teenager.

Not overly attractive, muscled, or funny, Tobey Maguire embodies desperate youth simply tryingto survive high school. Once again, that powerful innocence that McGuire carries with him through his career becomes a key asset in this role. Timing, nerdy, and spiritually soft, Maguire perfectly captures the qualities that make Parker a doormat that many of his fellow high school companions gladly walk all over.

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When Parker obtains his powers and starts to grow into a true superhero, it’s his humble origins that allow audiences to continue to connect with Parker even as he becomes superhuman, capable of stunts impossible to the human. He still remains unpopular and goofy even as he takes down bad guys. We suffer greatly when Peter’s beloved Uncle Ben dies because, like Parker, we were too focused on how cool it was to be Spider-Man to truly understand how “great power comes great responsibility” until that moment.

While a new generation of film-goers has grown up with Tom Holland as their Spider-Man, it cannot be understated that McGuire continues to be the precedent for Peter Parker’s character. This was only further highlighted inSpider-Man: No Way Home, where McGuire returned to the role of Peter Parker alongside Garfield and Holland. The film was a smashing success, and the coordination of all three Peter Parkers was a beautiful mosaic of how the character has evolved through the franchise. And yet, while each actor brings a new, exciting quality to their Spider-Man, Maguire’s is still the most lovable to audiences. Even in his older age, Maguire’s quiet demeanor, goofy personality, and uniquely innocent appearance make him the most relatable Spider-Man by far.

Related:Why Tobey Maguire Is Still the Best Peter Parker and Spider-Man Put to Live-Action Film

Yes, Tobey Maguire is amazing in the role of Spider-Man. Then why is it not the best of all Maguire’s movies? This is because theSpider-Manfranchise, as well as the Marvel franchise, is evolving. Raimi’s original trilogy was a success critically and financially. And yet, Tom Holland’sSpider-Manfilms have been wildly successful as well, signaling that the world is ready for a new rendition of Peter Parker.

The energy and characteristics of Spider-Man — while he remains a goofy kid trying to grow up while being a superhero — are changing. Tom Holland’s background in dance makes him a more agile performer, andhis stunts as Spider-Manare more complex and beautiful than Maguire’s. Increased budgets and new CGI technology mean these films have leaned further and further into the realm of science fiction. And while much of the franchise’s success is because Tobey Maguire’sSpider-Manblazed the trail for them, there is no doubt that the superhero will continue to grow and change from its origins.

Why Pleasantville Is Tobey Maguire’s Best Movie

So, why isPleasantvilleTobey Maguire’s best film? Because Maguire brought the character of David, and the world of Pleasantville to life in a way that few other actors could. Like Peter Parker, David is someone struggling on the edges of teenage society. And while David does not have any of the gravity-defying capabilities of Spider-Man, his presence as an outsider in the Pleasantville Universe does give him superhero-like abilities. Thrown into a foreign world that follows the rules to a T, David and his sister use their radical ideas and unique perspective of the world to help Pleasantville evolve into a community of free thinkers.

While David is responsible for this drastic change in the neighborhood, he still maintains his own air of childlike ignorance. A huge fan of the series, at first David has no interest in changing Pleasantville. He enjoys the monotony, how everything in this world goes exactly as planned. Like the town of Pleasantville, David has been stuck in his own ways; he has little interest in making friends, learning at school, or building a future for himself. Thus, in order to change the world around him, he must learn and grow right alongside them.

This dichotomy —maintaining youthful innocencewhile growing up — is a balance that Maguire has mastered throughout his career. The actor understands how to use boyish ignorance in balance with serious emotions, seamlessly moving between the two, which makes his role so believable. Just as we loved Peter Parker for his relatability, Maguire transformed Pleasantville from an interesting pitch into a rich, three-dimensional world that the audience could buy into. As viewers, we watch David grow, growing alongside him ourselves as we realize in what ways we are stuck in our old and unfounded beliefs.