The best Tobey Maguire movies, ranked

Tobey Maguire

Tobey Maguire is a Spider-Man that has not always done whatever a Spider-Man can.

Long before he was the first actor to portray the iconic Marvel character outside of low-budget television series deviating from the source material, he was an actor with an eclectic resume. He’s starred in low-key dramas, surreal and bonkers animated films, and some content that has even been blocked from release in the U.S. to this day.

As a result, it can be difficult to know what other films in Maguire’s repertoire to watch outside of his wall-crawling ventures. Anyone struggling need not worry, because as always, we’ve got you totally covered.

Below is our list of Tobey Maguire’s best movies. We did not count his trilogy as Peter Parker or any other Spider-Man films, as everyone already knows how good they are. (Yes, the third one does have some merit even though it’s goofy.) We used Rotten Tomatoes as our rough guide and also incorporated our own opinions.

Warning: This article contains spoilers. Please proceed with caution if you have yet to see every Spider-Man film ever made.

10. The Wizard (1989)

People may not remember this movie, but our subject is absolutely in it. This counts as his first on-screen appearance, and while some Maguire biographies have not bothered to mention it, we couldn’t make the same mistake! When you have time, go watch this 29 percent positive masterpiece of early video game culture schlock and know that you’re watching a legend come to life.

9. The Ice Storm (1997)

Directed by Ang Lee before he won major praise for making the kind of film that Eric Cartman once said was all award shows cared about, this movie has an 85 percent positive rating. It tells the story of two dysfunctional families in a time of immense societal change and was one of Maguire’s first major roles after a few years spent playing bit parts. He plays a young son with crazy relatives and really makes you believe that his character is desperate for change.

8. Fear and Loathing in Las Vegas (1998)

While it’s weird to see a man known for his fictional heroics play the kind of person who would not be allowed near children at a bus stop, Maguire sells the idea in this 50 percent positive film. While not a hit with critics, about 89 percent of audiences have liked it and it hammers home the legend of Hunter S. Thompson to future generations.

7. Pleasantville (1998)

Though this movie features an obvious allegory, it earned an 85 percent positive rating from critics and is worth watching for a number of reasons. Maguire has a great earnestness in his role as a fan of an old television show who gets sucked into the world his favorite characters inhabit. The music and effects still hold up to this day and it’s one of the final performances of the always excellent J.T. Walsh. (If you haven’t seen any of his work, watch this film and you’ll see why he’s sorely missed.)

6. Ride with the Devil (1999)

Let’s face it: just like how no one thinks Michael Bay has the ability to make a minimalist LGBTQ+ drama set in a coffee shop, no one thought Maguire could be a pro-Confederacy figure during the Civil War. And yet Maguire digs in with gusto here. Ride with the Devil was a bomb when it came out, but it has a 64 percent positive rating and features a stacked and interesting cast beyond our article’s subject, including Jim Caviezel before he went wild, Jeffrey Wright, and even Mark Ruffalo.

5. Don’s Plum (2001)

Though this film has no critical reception, it’s been praised by 62 percent of those who have seen it and is worth watching simply because of how difficult it is to find. Maguire and close friend and co-star Leonardo DiCaprio have successfully blocked it from release in North America, but there’s no real reason for them to have done so. The film centers around friends discussing life at a diner and there’s nothing controversial or crazy about it given their subsequent endeavors.

4. Seabiscuit (2003)

Seabiscuit

Maguire made this 77 percent positive movie between his best Spider-Man trilogy entries and it’s one of the better historical films out there. Here he plays John Pollard and lifts up all who watch him on the screen. While he’s often someone with a doofy charm, he would benefit from playing serious characters like this much more often ⏤ and so would we.

3. Brothers (2009)

Too often movies about soldiers and those who have been in either the Iraq or Afghanistan fiascoes make it seem like something glamorous. War is brutal and leaves significant scars, and Maguire showcases that in this 64 percent positive production. For making something that goes against the status quo, which much of the general public is fed by every other form of media they consume, this stands as one of Maguire’s best works.

2. Pawn Sacrifice (2014)

Maguire plays chess champion Bobby Fischer in this 71 percent positive biographical film. The work is fine, but it deserves a high spot on our list due to Maguire’s ability to tease the audience with a current of menace beneath the surface, which would hit the actual Fischer later on in life. It’s a shame we never get to see it fully play out on screen, but a sequel could be gloriously nuts.

1. Spider-Man: No Way Home (2021)

Spider-man Spider Man
by Keane Eacobellis

Surprise! We told you a Spidey film wouldn’t make this list and then lied! Sound familiar? If not, then you’re gonna have to study up on all things No Way Home and see it ASAP. This 94 percent positive production is definitely our pick for Maguire’s best role to date. He shines as the veteran hero of the web-slinging bunch and also quietly demonstrates how these movies can mold a life decades after appearing in one. With any luck, it won’t be the last time he dons his signature red and blue spandex.

This concludes our picks for the best Tobey Maguire movies made to date. What do you think of our assessment? Was there a film you would have added to the list or one you would have excluded? Let us know in the comments below.