Tobey Maguire’s 10 Best Movies, Ranked According to Letterboxd

While he’s most well-known for his role as the Web-Slinger from the Marvel universe, Tobey Maguire has been having fun swinging through Hollywood for quite some time. Both before and after he booked his gig as the most profitable superhero of all time, Maguire has proved himself as far more than just a wall-crawling hero when it comes to acting ability and film quality as a whole.

He’s been from the Marvel universe to war, from Vegas to old Hollywood, and so much more. The career of Tobey Maguire is one filled with some amazing movies to look back on—one filled with content that people have genuinely adored over the years. With Letterboxd becoming the newest go-to for movie reviews, coming close to eventually surpassing even the likes of IMDb one day, how do Tobey’s movies fare on the new platform?

10

‘This Boy’s Life’ (1993)

Letterboxd Rating: 3.6/5

While Mr. Maguire may not have a giant role in This Boy’s Life, but it’s pretty significant to his career and an all-around pretty good movie. This would be the first Hollywood movie Tobey ever received a credit for on his resume. In it, he plays a side character named Chuck Bolger, who is a preacher’s son with a rough drinking problem.

Maguire portrays this drinking problem with a gracious complexity that allows the character to really have impact and meaning on not just the plot but the character of Jack (Leonardo DiCaprio), aka Tobias Wolff, too. So, not only was it one of his first big roles, but it really showed off the kind of dramatic talent that he has under his belt.

9

‘Wonder Boys’ (2000)

Letterboxd Rating: 3.6/5

Wonder Boys has one of the coolest casts of the early 2000s. With the likes of Michael Douglas, Robert Downey Jr., Katie Holmes, and, yes, Tobey Maguire. When Douglas’ character’s wife leaves him, he’s sent on a journey that connects him closer to one of his lonely students and the complex relations between him and his lover.

Seeing a cast like this come together is a wonder, and they work incredibly well together. Wonder Boys shows off Maguire’s ability to have great chemistry with other actors, like the legendary Douglas. Coming only two years before his big Marvel debut, Maguire got to add another great dramatic role to his resume before he got his big breakout role.

8

‘Pleasantville’ (1998)

Letterboxd Rating: 3.7/5

Pleasantville is an absolute classic film that is definitely one of Maguire’s best. His character, David, and his sister, Jennifer (Reese Witherspoon), get sucked into a classic sitcom called “Pleasantville”. However, while they genuinely enjoy their time there, Jennifer’s more “modern” demeanor begins to completely disrupt life there and bring color to it.

It’s a super unique concept for 1998 and inspired a lot of films to come after. Movies like Disney’s Teen Beach movie take heavy inspiration from it and that’s a testament to how great of a film this is. The visuals that accompany it are also very inventive, as color re-enters the sitcom world as the plot moves along.

7

‘Deconstructing Harry’ (1997)

Letterboxd Rating: 3.7/5

Tobey Maguire plays an interesting character in Deconstructing Harry. The film is about a writer named Harry (Woody Allen) who has been writing about people in his life and the young actor plays one of said characters in the story. It’s a fascinating concept that Maguire depicts very well, and it allows him to have fun with who he’s playing, given the fact he’s a figment of this writer’s story.

Deconstructing Harry is a unique story with a thought-provoking message that keeps things feeling fresh and new with its concept. The way his friends and family begin to slowly push away from him because of the way he depicts them in his own stories is compelling and heartbreaking. It’s a story of self-expression unlike any other.

6

‘The Ice Storm’ (1997)

Letterboxd Rating: 3.8/5

Based on the novel by Rick Moody, The Ice Storm showcases the story of a small family getting caught in one of the worst ice storms in history. Despite its stacked cast and critical reception, this one flew under the radar over the years because of how much it didn’t earn at the box office. On a budget of $18 million, the film only grossed $8 million worldwide. Though, this doesn’t mean anything about the movie’s quality.

Maguire takes on the role of the son of the family, Paul Hood. While this role didn’t have many eyes on it when the movie released, it was still a big one for him in his career. He got to work with the likes of Elijah Wood, Sigourney Weaver, Kevin Kline, and Joan Allen. Getting the chance to act alongside titans like them is a gigantic moment for any smaller actor. His great performance helped out the movie, too. Because while it didn’t garner a lot at the box office, it still gained positive reviews from those who did, with the cast being mainly noted.

5

‘Fear and Loathing in Las Vegas’ (1998)

Letterboxd Rating: 3.8/5

Fear and Loathing in Las Vegas is another role of Maguire’s that is quite small but, regardless, still stands out in his career among the rest—for funnier reasons than to be assumed. The young actor at the time played a hitchhiker that the main characters pick up toward the beginning of the film, and boy does this end up being one of Maguire’s funniest-looking roles, wearing a ridiculous wig that makes him look almost unrecognizable. What makes it even funnier is that instead of shaving his head for the role, Maguire actually opted to rather have a bald cap and some CGI to make him look the way he does.

As a whole film, Fear and Loathing in Las Vegas is also enjoyable. It’s certainly not a perfect movie, but there’s a ton of fun to be had—most likely explaining the high scores on Letterboxd. Unfortunately, however, this was similar to The Ice Storm in the fact that it underperformed at the box office, regardless of if people liked it or not. Fear and Loathing in Las Vegas is a very stoner comedy type of film that has a lot of fun just being goofy.

4

‘Spider-Man’ (2002)

Letterboxd Rating: 3.8/5

Tobey Maguire was a very well-known actor before 2002—no doubt about it. His debut as the titular hero in Sam Raimi‘s Spider-Man, however, pushed him to a level of fame and stardom that he’d never had before. With Spider-Man being one of the most popular fictional characters ever, being the first live-action actor to take on the role in a theatrical film meant that Maguire had all eyes on him when Spider-Man was released.

Thankfully, with both his performance and the wonderful direction by Raimi, Spider-Man ended up being a wonderful film that helped get superhero movies to where they’re at today. It is part of that early 2000s era of superhero movies that helped set the bar used as the standard these days. It’s an incredible origin film that keeps the plot simple so the story and character arcs can feel deeper and more complex.

3

‘Spider-Man: No Way Home’ (2021)

Letterboxd Rating: 3.8/5

After the less-than-ideal trilogy capper, Spider-Man 3, released and pretty much killed Maguire and Raimi’s series, people never expected this guy to come back and step into the role of Spider-Man ever again—not even in the Spider-Man: Into the Spider-Verse movies. But it was in Spider-Man: No Way Home, the third Tom Holland Spider-Man movie, that he got to finally come back once again.

Not only did his and Andrew Garfield‘s involvement break both the internet and the box office, but they also simply made the movie even better than before. Their supporting roles in the third act are not purely for nostalgia, but genuinely add so much to Holland’s Peter’s character arc to the point where they really do feel necessary. Spider-Man: No Way Home finds itself being one of the best Spider-Man movies in quite some time and a big part of that genuinely is Maguire and Garfield’s involvement.

2

‘Babylon’ (2022)

Letterboxd Rating: 3.8/5

Damien Chazelle‘s 2022 flick, Babylon, is a project that takes the idea that all art is somewhat of a remix of itself and tells a story about it through the lens of the 1920s. This was a pretty big time for the industry, as it was the era in which Hollywood began to make a large shift from silent film to that of sound—an era of history for movies that hasn’t been super explored yet.

Within Babylon, Maguire plays James McKay, who is the part of the movie that really dives deep into the “underground” of Hollywood and all of the less-than-savory things that come with being successful in that business. He helps accentuate the darker side of the Hollywood world and that, in turn, allows the film to hone in more on the themes it’s trying to convey.

1

‘Spider-Man 2’ (2004)

Letterboxd Rating: 3.9/5

There’s no question that Spider-Man 2 is an all-around beautiful and phenomenal movie. Known commonly as one of the best superhero movies ever made—even up there with the best sequels, too—Spider-Man 2 tells a Peter Parker story first and foremost and asks the question whether being Spider-Man is truly worth it, even if it means the destruction of Peter Parker’s personal life.

It’s an incredible tale that not only weaves a great story, but provides some thrilling battles (like who could forget that train fight?) to keep action-lovers entertained. At the end of the day, though, it’s almost structured more like a drama rather than an action film. Maguire brings his acting A-game in this one and provides what is easily his best performance in the series.

NEXT: Peter Parker’s Character Arc in Every Spdier-Man Movie, Ranked