11 Great Tobey Maguire Movies And How To Watch Them

Tobey Maguire in Spider-Man
(Image credit: Sony Pictures Releasing)

Whether he's in massive superhero movies like Spider-Man or awards contenders like Seabiscuit, Tobey Maguire has long been one of Hollywood's most interesting actors. And, with him recently finding his way back into the spotlight after what seems like a lifetime away from acting, now seems like a good time to look back on his best work.

The list of Tobey Maguire’s best movies is full of great wonders like the aforementioned comic book adaptation and biographical dramas, as well as offbeat comedies and dark psychological thrillers. Let’s break some of those down now…

Tobey Maguire in Spider-Man 2

(Image credit: Sony Pictures Releasing)

The Spider-Man Movies (2002 - 2007)

Although he’s not everyone’s favorite Peter Parker, Tobey Maguire was still the first actor to don the iconic red and blue spandex suit on the big screen when he appeared in Sam Raimi’s 2002 Spider-Man movie. Maguire would go on to play the character in the Raimi franchise two more times before stepping away when Spider-Man 4 failed to launch. 

Tom Holland and Andrew Garfield may receive more praise for their portrayals of the web-slinger, Tobey Maguire will always have a special place in the hearts of millions of Marvel Comics fans for his boyish charm. (Just don’t talk about Bully Parker in Spider-Man 3.)

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Tobey Maguire in Seabiscuit

(Image credit: Universal Pictures)

Seabiscuit (2003)

Three broken men in Great Depression-era America are brought together by a promising yet unruly race horse after being tested by their own personal battles. Charles W. Howard (Jeff Bridges) has the horse named Seabiscuit, Tom Smith (Chris Cooper) can train him, and hotshot jockey Red Pollard (Tobey Maguire) can ride him; only if they don’t get in the way of themselves.

Based on the true story of one of the most improbable race horses, Gary Ross’ 2003 drama, Seabiscuit, sees Tobey Maguire in top form as a fiery young man who’s got something to prove. There are times throughout this Academy Award-nominated film where Maguire is trying to prove himself to the world just like his character.

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Reese Witherspoon and Tobey Maguire in Pleasantville

(Image credit: New Line Cinema)

Pleasantville (1998)

Siblings Jennifer (Reese Witherspoon) and David (Tobey Maguire) are transported to the black-and-white world of the fictional sitcom, Pleasantville, when a TV repairman (Don Knotts) offers them an escape from the complexities of modern life. Trapped in the picturesque, yet conservative town, Jennifer and David attempt to get back to the real world, but only after fixing the community’s problems.

It is hard to imagine anyone else besides Tobey Maguire playing David in the 1998 Gary Ross satirical comedy, Pleasantville. One of Maguire’s most charming and heartfelt performances, the movie sees the young actor in some surprisingly meaningful and emotional conversations, especially with Joan Allen and William H. Macy, along the way.

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Tobey Maguire and Michael Caine in The Cider House Rules

(Image credit: Buena Vista Pictures Distribution)

The Cider House Rules (1999)

Homer Wells (Tobey Maguire) has spent much of his life living and working at a Maine orphanage under the care and watchful eye of Dr. Wilbur Larch (Michael Caine), a complicated yet loving father figure. As Homer becomes more aware of the world around him, he strives to break out and find his place in the world. But, things always come full-circle.

The winner of two Academy Awards, Lasse Hallström’s The Cider House Rules is a beautiful and complex drama about love, life, and new beginnings while also touching on far more serious matters. Tobey Maguire’s take on Homer is exactly what the movie needed, as he is able to effortlessly play a young man in the midst of crisis.

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Robert Downey Jr. and Tobey Maguire in Wonder Boys

(Image credit: Paramount Pictures)

Wonder Boys (2000)

Curtis Hanson’s 2000 dramedy, Wonder Boys, follows Grady Tripp (Michael Douglas), a brilliantly complicated college professor struggling to complete his second book. His situation is made all the more worse when the woman (Frances McDormand) with whom he’s having an affair announces she’s pregnant, his agent (Robert Downey Jr.) shows up unannounced, and one of his students (Tobey Maguire) has a severe mental break.

Pretty much everyone in Wonder Boys is giving it their all, but one of the most promising performances is that from Tobey Maguire. His character, James Leer, is a fundamentally broken individual who is prone to rash decisions (including theft and killing a dog), but still has a certain quality that makes it impossible to give up on him.

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Tobey Maguire in The Great Gatsby

(Image credit: Warner Bros. Pictures)

The Great Gatsby (2013)

Shortly after arriving in 1920s New York, young and idealistic Midwesterner Nick Carraway (Tobey Maguire) gets caught up in the city’s electric social scene, before forming a close-knit bond with his ultra-wealthy and mysterious neighbor, Jay Gatsby (Leonardo DiCaprio). When Gatsby learns that Nick is cousins with the love of his life, the whole matter becomes all the more complicated for everyone involved.

Baz Luhrmann’s 2013 adaptation of F. Scott Fitzgerald’s landmark novel The Great Gatsby perfectly captures the glitz, glamour, excess, and drama of the “Roaring Twenties,” and Tobey Maguire’s Nick Carraway is there to experience it all for us. The way in which Carraway’s infatuation with Jay Gatsby and the world he’s built is shown is masterfully told through Maguire’s portrayal.

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Tobey Maguire in Pawn Sacrifice

(Image credit: Bleecker Street)

Pawn Sacrifice (2015)

When American chess grandmaster Bobby Fischer (Tobey Maguire) is tasked with taking on his Soviet counterpart Boris Spassky (Liev Schreiber), he quickly discovers he is in for one hell of a challenge. But, his duel against the Russian grandmaster pales in comparison to one he fights against his own personal demons and extreme paranoia.

Edward Zwick’s Pawn Sacrifice is a stressful, anxiety-inducing drama that is more about paranoia and the sacrifices one must make in order to achieve greatness. Bobby Fischer’s pain, suffering, and deteriorating mental state throughout the movie are all shown masterfully by Tobey Maguire’s convincing performance, one of the best of his career.   

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Tobey Maguire in The Ice Storm

(Image credit: 20th Century Fox)

The Ice Storm (1997)

The Hood family is pushed to its limits over the course of Thanksgiving weekend when Elena (Joan Allen) discovers her husband, Ben (Kevin Kline), is having an affair with their neighbor. Things get even worse for the pair when they are invited to a very unorthodox party. Their children, Wendy (Christina Ricci) and Paul (Tobey Maguire), also endure their own personal struggles during the complicated holiday season.

Ang Lee’s The Ice Storm doesn’t get brought up nearly as much as the director’s other work, but this portrait of a family in crisis is one of his strongest efforts. Each person in the family is going through their own personal struggles and makes you feel less alone in some odd way. Despite this being one of his first major roles, Tobey Maguire makes a case for being one of the best and most understated actors of the era.

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Tobey Maguire in Deconstructing Harry

(Image credit: Fine Line Features)

Deconstructing Harry (1997)

When asked to return to his old college to receive an honorary degree, successful novelist Harry Block (Woody Allen) is forced to confront people from his past, as well as the characters they inspired. The movie, which bounces between comedy, romance, and tragedy (like much of Allen’s earlier works), features Block’s characters played by Robin Williams, Julia Louis-Dreyfus, and Tobey Maguire.

Seemingly forgotten 25 years after its release (it’s hard to find these days), Deconstructing Harry features one of the best characters inspired by Woody Allen, Tobey Maguire’s Harvey. Though he’s only in the movie briefly, Maguire is out-of-the-world and out-of-his-mind as the sex-crazed young writer who visits a shrink and escort to overcome his frantic mental state.

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Jake Gyllenhaal and Tobey Maguire in Brothers

(Image credit: Lionsgate)

Brothers (2009)

When Marine Sam Cahill (Tobey Maguire) is believed to have died in combat while deployed to Afghanistan, his ex-felon brother, Tommy (Jake Gyllenhaal), makes up for his past and takes care of his sister-in-law, Grace (Natalie Portman), and young nieces. But, when a broken Sam is rescued, the entire situation takes a dramatic and traumatizing turn.

Jim Sheridan’s Brothers has great performances across the board, but Tobey Maguire’s take on a Marine who has suffered a fate possibly worse than death really drives the film’s second half. The pain, paranoia, and loss can be felt by just looking at his tortured face. It would be terrifying if it weren’t so heartbreaking.

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Tobey Maguire in The Good German

(Image credit: Warner Bros. Pictures)

The Good German (2006)

Sent to Germany to cover negotiations following the conclusion of World War II, war correspondent Jake Geismer (George Clooney) soon finds himself in the middle of a dangerous situation, after the body of his driver, Corporal Patrick Tully (Tobey Maguire), is pulled from a river with a load of cash in his possession. Further complicating matters is Jake’s former lover Lena Brandt (Cate Blanchett), who is trying to find her missing husband.

Steven Soderbergh’s 2006 black-and-white drama The Good German is a throwback to the crime dramas of yesteryear where no one can be trusted. Tobey Maguire does a fantastic job of playing a seemingly innocent man whose past transgressions are exposed one at a time. He’s almost perfect as the GI with secrets to hide.

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Tobey Maguire in Fear and Loathing in Las Vegas

(Image credit: Universal Pictures)

Bonus: Fear And Loathing In Las Vegas (1998)

Tobey Maguire only briefly appears in Terry Gilliam’s 1998 adaptation of Hunter S. Thompson’s semi-autobiographical novel, Fear and Loathing in Las Vegas, but his turn as the hitchhiker picked up by Raoul Duke (Johnny Depp) and Dr. Gonzo (Benicio del Toro) in the film’s opening minutes is too good to pass up. His reserved and terrified character does a wonderful job of establishing the madness of the movie’s central duo while also setting up the drug-fueled insanity of the world in which the audience is about to enter.

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Well, this just about wraps up Tobey Maguire's best movies, that is, until a certain superhero film finds its home in the streaming world. Oh, and there's also Damien Chazelle's mysterious Babylon to look forward to, as well. 

Philip Sledge
Content Writer

Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop barking at the mailman, or chatting about professional wrestling to his wife. Writing gigs with school newspapers, multiple daily newspapers, and other varied job experiences led him to this point where he actually gets to write about movies, shows, wrestling, and documentaries (which is a huge win in his eyes). If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.