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Every Tobey Maguire Movie Ranked From Worst To Best

The first Spider-Man of the new millennium, actor Tobey Maguire may be best known as Peter Parker to most audiences, but it isn't the only role he'll be remembered for. Though he hasn't been as prolific as his co-stars Kirsten Dunst or J.K. Simmons, Maguire's career has run the gamut from action to drama to romantic comedy. Getting his start playing slacker teenagers, he came to prominence in the mid to late '90s with a string of indie films that put him on the map before making his debut as a superhero in 2002.

In his nearly 30-year career, Maguire only starred in around 20 films, seemingly disappearing after the Spider-Man trilogy. But when he does pop up in a new film, he never fails to shine. He's worked with acclaimed directors like Sam Raimi and Ang Lee, alongside some of the industry's biggest names, including Sigourney Weaver, Jeff Bridges, Willem Dafoe, Leonardo DiCaprio, George Clooney, Cate Blanchett, and Frances McDormand. But they've not all been classics. From worst to best, here's every Tobey Maguire movie ranked.

20. Revenge Of The Red Baron

Schlock producer Roger Corman may be best known for such B-movie ripoffs as "Carnosaur" and "Battle Beyond The Stars," but he's made some gems too, including the 1960 classic "Little Shop Of Horrors." The forgotten 1994 family film "Revenge Of The Red Baron," however, isn't among his best, though it's notable today for starring a young Tobey Maguire. The future "Spider-Man" star here plays Jimmy, a wayward and delinquent teen whose mother (Laraine Newman) leaves him in the care of his father (Cliff De Young). There he reconnects with his doddering grandfather, played by Hollywood icon Mickey Rooney, who just so happens to be the World War I fighting ace who shot down the Red Baron.

But just when Jimmy learns about his grandfather's past, none other than the Red Baron himself returns from the grave looking for revenge. With his soul inhabiting the body of a doll in a toy biplane, it's up to Jimmy and his grandfather to stop the Red Baron once again. An attempt at a heartfelt family movie, "Revenge Of The Red Baron" is every bit as goofy and awful as it sounds. Though campy and an easy skip for fans of Maguire, a 2005 retro review in Dread Central found the premise interesting, lamenting that it wasn't used as the basis for a horror movie instead.

19. Cats & Dogs

Another goofy family film, "Cats & Dogs" was released a year before Maguire would make his career-defining performance as Peter Parker, here voicing a friendly beagle belonging to the Brody family. The movie exposes the hidden world and secret life of pets living right beneath human noses, and the never-ending war between, well ... cats and dogs. Rather than being innocent animals, "Cats & Dogs" reveals that they are actually intelligent creatures with advanced technology that they cleverly hide from their human owners. 

Leading the charge is Lou (Maguire), a naive beagle pup who gets caught up in the canine war with their feline foes. Wrongly identified as their newest top-secret agent in the field, Lou is recruited by Butch (Alec Baldwin), a German shepherd. He is tasked with a critical mission to stop the cats from completing a new chemical weapon that will render all humans allergic to dogs. Also starring Jeff Goldblum as Lou's human owner, the film is full of spy action and narrative twists. Though it was a surprising success at the box office, it took a thrashing from critics. Nevertheless, it earned itself two direct-to-video sequels, with Neil Patrick Harris replacing Maguire as Lou.

18. Joyride

Tobey Maguire's 1997 film "Joyride" boasts an eclectic cast that includes not just Maguire, but "Batman" star Adam West, Benicio Del Toro, and Wilson Cruz. Maguire stars as J.T., whose friend James (Cruz) is the son of the local motel's owner. When J.T. becomes smitten with a hotel guest named Tanya, the trio steals a car and goes on a joyride. But their night of fun takes a dark turn when the three friends discover a dead body in the trunk of the car. 

Suddenly the target of local detectives, they're even more surprised when the woman they stole the car from helps protect them. But when it's revealed that the woman is actually a trained assassin, James, Tanya, and J.T. find themselves in way over their heads. Things go from bad to worse, however, when the woman attempts to turn Tanya against her two friends. A forgettable movie, it was hardly seen at the time and it proved unloved by those who did give it a watch. Critics seemed to agree that the film was ultimately just a generic crime thriller full of unlikable, cliched characters and a paint-by-numbers story, with the A.V. Club calling it "depressingly mediocre." 

17. Don's Plum

In 2001, Tobey Maguire starred with his good friend Leonardo DiCaprio in "Don's Plum," a low-budget indie drama. Many believe the film, heavily improvised by the actors and with little narrative structure, captures the real-life nature of the two young stars' genuine friendship. During those days, Maguire and DiCaprio were regulars in the gossip columns for their nights on the town, and in the film, they star as two friends who meet weekly at a club, and bring a different girl with them each time. 

Never shown in theaters in the United States, the film was plagued with post-production issues (via The Guardian). DiCaprio and Maguire had apparently only agreed to star in it after it was pitched as a short film, but producers went behind their backs and edited it into a feature-length movie. According to some, Maguire was miffed about the use of some footage, which was largely improvised. Seemingly acknowledging that his character was inspired by his own life, he reportedly felt it revealed too much about himself. After a court battle, producers cut up the film and released it outside the U.S. and Canada (these days though, it's available to watch on Youtube). Though an oddity for its insight into Maguire's pre-fame days and friendship with DiCaprio, it's otherwise a disappointing, disjointed film with very little to say. 

16. Boss Baby

Another animated voice role alongside Alec Baldwin, Tobey Maguire helped out the cast of "Boss Baby" by playing the adult version of the older brother Timmy, who serves as the film's narrator. Oddly enough, the CGI animated film saw Baldwin and Maguire — who had both starred in "Cats & Dogs" — in a war with puppies. Timmy is an ordinary seven-year-old boy whose life is turned upside down by the arrival of a newborn baby brother. But the tension soon subsides when Timmy learns that his new sibling is actually a secret agent working for Baby Corps, an organization locked in an endless war with Puppy Co., who are vying for adults' affection.

Despite middling reviews from critics and audiences alike, the film became a massive hit at the global box office to the tune of $528 million. With that kind of success, it wasn't long before a sequel popped up: "Boss Baby: Family Business." Maguire didn't return to reprise his role and was replaced by "X-Men" star James Marsden. From there, streaming giant Netflix greenlit a CGI animated series, "Boss Baby: Back In Business." While it's not one of his best films, it might be his most successful franchise-starter after "Spider-Man."

15. The Good German

Acclaimed director Steven Soderbergh assembled three big stars for his 2006 film "The Good German," with Tobey Maguire joined by George Clooney and Cate Blanchett. Set in the years following the Allied victory in World War II, the film is a callback to post-war noir thrillers, shot entirely in black and white to recapture that era's distinctive tone. In the film, Maguire appears as Corporal Patrick Tully, an American soldier and driver for news reporter Jacob Geismer (Clooney). 

When Geismer sets out to help his former girlfriend Lena Brandt (Blanchett) find her husband Emil, they soon discover that Tully is more than he appears. But Jacob and Lena aren't the only ones out looking for Emil, whose activities have made him the target of British, American, and Russian agents, each for their own reasons. An homage to old Hollywood, "The Good German" didn't prove as memorable as Soderbergh's other works alongside Clooney, with The Guardian calling the film a "cynical take on 1940s thrillers" and dismissing it as trite, with its big stars giving lackluster performances.

14. The Details

Reteaming with his old friend Leonardo DiCaprio — who this time acts only as the film's narrator — Tobey Maguire headlines the little-seen 2011 indie romantic drama "The Details" opposite his "Spider-Man" co-star Elizabeth Banks. Maguire plays Dr. Jeff Lang, husband to Nealy (Banks), whose various missteps just keep piling up, all while a family of raccoons is driving him up the wall. From cheating in medical school to accidentally poisoning a house cat, there is no end to the trouble he finds himself in. Never mind the affair he has with his lonely neighbor, or his other affair with his best friend's wife.

Plagued by every bad choice he makes, Jeff is soon forced to fess up to everything when he unwittingly becomes part of a serious crime and finds himself being blackmailed. Though the critical consensus wasn't stellar, NPR praised the film at least for its ambition, calling "The Details" "effectively immersive ... a satisfying exploration of keeping secrets and living in spite of paralyzing guilt."

13. Ride With the Devil

Oscar-winning director Ang Lee brought back Tobey Maguire from his film "The Ice Storm" when he ventured into the Wild West for the 1999 drama "Ride With the Devil." Maguire would be joined by Jeffrey Wright, Skeet Ulrich, Jim Caviezel, and pop star Jewel in the adaptation of the novel "Woe To Live On" by Daniel Woodrell. Set in the middle of the American Civil War, Maguire plays Jack Roedel, who along with his good friend Jake Chiles (Ulrich) joins with freed slave Daniel Holt (Wright) and Southern traditionalist George Clyde (Simon Baker) to fight with a group of Missouri Bushwackers — pro-Confederacy irregulars — against the pro-Union Jayhawkers. 

After a wave of big westerns in the '90s like "Unforgiven" and "Tombstone," Ang Lee's first stab at the genre was a good one, but it only received mixed reviews. Roger Ebert gave it just two stars, and called out his frustration with Maguire's performance in particular, saying "Tobey Maguire's tone — tight, inward, controlled — is beginning to wear on me." Still, it wasn't all bad, with Variety's review giving the cast their due, calling "Ride With the Devil" "a brutal but sensitively observed film about the fringes of the Civil War."

12. Spider-Man 3

Following one of the most celebrated superhero movies of all time, Tobey Maguire reunited with director Sam Raimi and actors Kirsten Dunst, James Franco, and J.K. Simmons for "Spider-Man 3" in 2007. The film sees Peter Parker still struggling to juggle a superhero life with his relationship with Mary Jane. But when he comes across an alien ooze that bonds to him, it doesn't just give him a new costume with incredible new powers, but twists him into an angrier, bitter superhero, endangering his life and his relationships.

At the same time, his best friend (Franco) transitions into an enemy after discovering that Peter is in fact Spider-Man, the man who killed his father. After Peter jettisons the black ooze suit, it turns snarky reporter Eddie Brock (Topher Grace) into the deadly villain Venom, just as fugitive criminal Flint Marko (Thomas Haden-Church) — the man who killed his uncle Ben — becomes the malevolent Sandman. Suddenly, Peter is forced to do battle with not one, but three new baddies. 

Unfortunately, the villain overload didn't do any favors for an already overstuffed plot, and the result was a murky mess of a movie that proved a disappointing end to the trilogy of Maguire's "Spider-Man" films from Sam Raimi. Still, it's packed with top-notch action, and faithful interpretations of classic Spidey villains. Thankfully, nearly a decade and a half later, Maguire would have a chance to go out on a much higher note.

11. Pawn Sacrifice

The 2014 biopic of chess prodigy Bobby Fischer, "Pawn Sacrifice" sees Maguire tackle a real-life historical figure. Alongside Liev Schreiber as Russian chess champ Boris Spassky, Maguire impressed critics with a triumphant performance as the youthful genius. Bobby Fischer came to symbolize America's resilient spirit when he'd square off against powerhouse players from the Soviet Union at the height of the Cold War, a time when the Soviets dominated the game on its biggest stage. 

The film chronicles Bobby Fischer's life from childhood up through his World Chess Championship in Iceland in 1972. It details how the U.S. government used him as a part of their propaganda war with their rivals in the Eastern Bloc, and how he struggled with the pressure of his elevated profile. Though Roger Ebert of the Chicago Sun-Times only awarded the film two stars, he lauded Maguire for his turn as Bobby Fischer. While he noted the lack of exploration of the depths of Fischer's complicated life, he did recognize that the movie worked "thanks in large part to the movie's greatest asset: Maguire's edgy, charismatic performance."

10. The Great Gatsby

Based on the famous F. Scott Fitzgerald novel, this adaptation of "The Great Gatsby" would see Tobey Maguire take on the role of Nick. Directed by Baz Luhrmann, it tells the story of author Nick Callaway (Maguire) as he relocates from the Midwest to New York City after World War I, moving into a cottage near his cousin Daisy (Carey Mulligan).

There, Nick becomes enthralled by the life of his new neighbor, the wealthy Jay Gatsby (Leonardo DiCaprio), and along with Daisy (and her unfaithful husband Tom, played by Joel Edgerton), he becomes drawn into his complicated life. Knee-deep in the high-stakes drama of love, passion, deceit, and murder, Callaway suddenly has all the material he needs to write his next book. Despite some notable differences from the source material, "The Great Gatsby" is generally regarded as a faithful interpretation. Thanks in no small part to the performances of its cast, including Maguire's new take on Nick, "The Great Gatsby" proved a hit at the box office

9. Wonder Boys

The highly acclaimed 2000 drama "Wonder Boys" starred Maguire alongside Michael Douglas, Robert Downey Jr., Katie Holmes, and Frances McDormand, in an adaptation of the novel by acclaimed author Michael Chabon. Maguire plays James Leer, a young but gifted writing student in the class of Professor Grady Tripp (Douglas). Distant and aloof, James is a troubled young man, but once Tripp realizes his enormous talents, the teacher wants to help him. After the two become an inseparable pair, Tripp's trusting nature is tested when he begins to suspect that his star student is manipulating him.

When James encounters Tripp's editor Terry Crabtree (Downey Jr.), the two begin an awkward love affair, which also helps James's creative aspirations. But Tripp is soon faced with a decision that will haunt him when he realizes how James has been using him.  Nominated for three Academy Awards, including best adapted screenplay, "Wonder Boys" cemented Maguire as one of Hollywood's brightest up-and-coming talents.

8. Brothers

Jake Gyllenhaal, once considered to replace Tobey Maguire as Spider-Man back in 2004, instead starred alongside him in the 2009 film "Brothers." Maguire plays Sam Cahill, a young married soldier who is presumed to have been killed in action. While he spends time in a foreign prison undergoing torture and is forced to kill a fellow soldier, Sam's brother Tommy (Gyllenhaal) — believing Sam dead — becomes a father figure to his children and a companion to his wife Grace (Natalie Portman). But when Sam is discovered alive and released from captivity, he comes home to a world that does not welcome him with open arms.

Suffering from a severe form of PTSD and finding his brother has taken his place, Sam struggles to reintegrate into society and lashes out. A thoughtful examination of the toll that war takes on even our toughest soldiers, "Brothers" was given three and a half stars by Roger Ebert, who called out Maguire's masterful performance, saying, "This becomes Tobey Maguire's film to dominate, and I've never seen these dark depths in him before. Actors possess a great gift to surprise us, if they find the right material in their hands." 

7. Seabiscuit

Once he had made a name for himself as a comic book superhero, Tobey Maguire turned to historical drama in the 2003 film "Seabiscuit." Set in the middle of the Great Depression, the film follows a famous underdog stallion called Seabiscuit and his trainer, Red Pollard. They would go on to become a championship team in the 1940s, and a pop culture sensation that captured the attention of the masses. Raised by a poor family, Pollard leaves home and becomes a horse trainer and jockey. But after a chance encounter with struggling tycoon Charles S. Howard (Jeff Bridges), Pollard is hired to work with his newest horse, a temperamental colt descended from a prized thoroughbred. 

The horse, Seabiscuit, is seen as too small and fiery to compete at the highest levels, but with Pollard's help, the pair soon begin winning races and are swept up in the excitement of their underdog success story. Together, the outcast horse and the overlooked jockey set out to beat the best horse in the game — Triple Crown winner War Admiral. "Seabiscuit" was a big hit for Maguire, nominated for seven Oscars, including best picture.

6. The Ice Storm

Director Ang Lee's "The Ice Storm" is a complex moral tale of love and fidelity, with Tobey Maguire and Christina Ricci playing the teenage children of stars Kevin Kline and Joan Allen. The story of two married couples who begin experimenting outside their marriage is mirrored by their troubled kids, testing new boundaries with sex, drugs, and alcohol.

The story begins in the mid-1970s when the two couples — Ben and Elena Hood and Jim and Janey Carver — participate in a swingers "key party" on the weekend of Thanksgiving, where attendees will trade spouses for extramarital affairs. In the midst of the adult goings-on, teens Paul and Wendy Hood are caught up in their own experimentations with the Carvers' two sons and Paul's crush, Libbets, while a dangerous ice storm descends on the town. 

Lauded as one of 1997's best films, "The Ice Storm" takes a deep dive into the boredom and frustration felt at a time of great upheaval in the American family. Elijah Wood, Sigourney Weaver, and Katie Holmes round out the all-star cast.

5. Pleasantville

In 1998, Tobey Maguire starred alongside actress Reese Witherspoon in the fantasy comedy "Pleasantville," where they play a pair of twins with opposite personalities. While Jennifer is a popular, flirty high schooler, her brother David is more shy and awkward, unhappy with his home life and obsessed with 1950s television, especially the sitcom "Pleasantville." When a mysterious TV repairman (classic TV star Don Knotts) arrives and gives David a new remote control, they suddenly find themselves transported to the black and white world of "Pleasantville," forced to play the parts of Bud and Mary Sue Parker: children in a perfect sitcom family.

Soon, David learns that the world he idolized isn't as perfect as he'd imagined, while Jennifer comes to appreciate it for its many charms. "Pleasantville" is a fun adventure that mixes the wholesomeness of classic sitcoms with the edginess of '90s movies like "Clueless" or "Empire Records." Praised for its quaint story and impressive visual recreations of 1950s America, reviewers gave the film high marks for its ability to capture the seemingly idyllic but deeply flawed world of the past.

4. The Cider House Rules

"The Cider House Rules" stars Tobey Maguire, Michael Caine, Charlize Theron, J.K. Simmons, and Paul Rudd. It tells the story of Homer Wells (Maguire), who grows up in an orphanage run by the kind and gentle Dr. Larch (Caine). Homer is recognized by Larch as a bright young man and entrusted with many responsibilities, but he refuses to assist Larch in the abortions he is frequently called on to perform. Eventually, rather than continue working for Larch as the doctor had hoped, Homer chooses to leave the orphanage. He takes a job at an apple orchard on the estate of his new friend, Wally Worthington (Rudd).

But when Worthington, a pilot, goes off to fight in the war, Homer begins an affair with Candy (Theron), Wally's lonely wife. Later, the pregnancy of one of the worker's wives forces Homer to realize that life isn't as black and white as he had initially believed. A major awards contender, "The Cider House Rules" is Maguire's most critically acclaimed drama, one that helped to establish him as one of Tinseltown's next big rising stars. 

3. Spider-Man

Following critical praise for his performances in "The Cider House Rules" and "Wonder Boys," Tobey Maguire secured his breakout role as Peter Parker in 2002's "Spider-Man." Directed by horror filmmaker Sam Raimi, Maguire became the definitive Spider-Man for an entire generation, capturing just the right amount of boyish charm and heroic toughness. At a time when comic book films weren't guaranteed box office juggernauts like they are now, it's not an exaggeration to say that Maguire's turn as the title hero helped launch the genre into a bold new era. 

As Peter Parker, Tobey Maguire gave audiences their first look at Spider-Man's origin story on the big screen: How he was bitten by a radioactive spider and vowed to fight crime after watching his Uncle Ben die in a botched robbery. And when his best friend's father (Willem Dafoe) experiments on himself and becomes the insidious Green Goblin, Spider-Man leaps into action to save the city. Though it takes a few small liberties with the original comics, "Spider-Man" was a box office smash, hailed as one of the best comic book adaptations of the era.

2. Spider-Man 2

Returning in 2004 to the role of Peter Parker, Tobey Maguire swung back into action, this time against one of the character's most iconic foes, Doctor Octopus (Alfred Molina). Developing a new power source, Otto Octavius crafts a set of artificially intelligent mechanical arms, but when he loses control of them, they warp his mind and turn him into a murderous supervillain. Peter, meanwhile, is overwhelmed trying to balance his personal and superhero lives, and loses Mary Jane, who becomes engaged to another man. After an emotional breakdown, Peter loses his powers and is forced to quit being Spider-Man. 

But when Octavius becomes a threat to the city, Peter Parker must confront his responsibility to stop the emerging menace. Though it didn't match its predecessor's box office, "Spider-Man 2" is often called a "perfect" superhero movie. Delving even deeper into the character, the film stands as a testament to everything that makes Spider-Man great, from the conflict between colorful heroes and villains to Peter Parker's struggle to maintain a personal life while secretly suiting up as Spider-Man. And it wasn't just audiences who loved it: The film garnered near-universal acclaim from critics, which was rare in the days before the MCU.

1. Spider-Man: No Way Home

Although almost 15 years have passed since he last suited up as Spider-Man, Tobey Maguire remains as beloved as ever as Peter Parker, and his portrayal of the wall-crawler is for many the gold standard. So when rumors began circulating that the actor might be reprising the role for 2021's "Spider-Man: No Way Home" alongside Tom Holland and fellow Spidey Andrew Garfield, it seemed almost too good to be true. Despite a tight-lipped production, denials from its stars, and an even more secretive marketing campaign, the truth was eventually revealed: Maguire did indeed return as Peter Parker for the third MCU Spider-Man film.

Arriving with Garfield's Spider-Man from other dimensions, the three Spider-Men team up to save the multiverse when a spell cast by Doctor Strange goes awry. Together, they must fight their old villains, and hope to cure them of their conditions, before repairing all of reality. Ultimately, "Spider-Man: No Way Home" is more than just a crowdpleaser driven by stunt casting; It's a wholly satisfying thrill ride from start to finish.