The 10 Most Underrated Tobey Maguire Movies, Ranked (From Least to Most Underrated)

Tobey Maguire is best known worldwide for bringing a certain web slinger to life, but his filmography stretches far beyond superhero suits. Across dramas, literary adaptations, historical pieces, and quirky indies, he has taken on roles that show careful craft and an eye for distinctive stories.

This list gathers ten titles that highlight that range. You will find collaborations with acclaimed directors, adaptations of notable books, and character studies that lean on strong writing and memorable ensembles. Each entry includes the kind of details that help you decide what to watch next.

‘The Good German’ (2006)

Steven Soderbergh directs this black and white mystery set in Berlin just after the Second World War. Maguire plays a volatile American driver whose path crosses with a war correspondent played by George Clooney and a displaced woman portrayed by Cate Blanchett. The film uses period staging and classical studio techniques to match its setting, including traditional lighting setups and vintage framing choices.

Production embraced an old Hollywood approach from sound recording to costume design. Scenes were staged on backlot environments that evoke the rubble of a defeated city, with newsreel style inserts and a score that leans into orchestral suspense. Maguire’s character functions as a catalyst for the plot’s overlapping agendas and shifting loyalties.

‘The Details’ (2011)

This dark comedy from writer director Jacob Aaron Estes casts Maguire as a suburban doctor whose ordinary life unravels after a battle with raccoons tears up his lawn. The chain of consequences pulls in characters played by Elizabeth Banks, Laura Linney, Ray Liotta, and Kerry Washington. The story blends domestic mishaps with moral missteps, moving from neighborhood squabbles to serious fallout.

The production was set in the Pacific Northwest with locations that underline the contrast between quiet streets and escalating trouble. Its release combined limited theatrical play with video on demand, which helped the film find an audience beyond a standard rollout. The screenplay’s structure follows a domino pattern where one bad decision creates the next.

‘Ride with the Devil’ (1999)

Ang Lee adapts Daniel Woodrell’s novel about irregular fighters on the Missouri Kansas border during the American Civil War. Maguire portrays a German immigrant who joins a group of bushwhackers alongside characters played by Skeet Ulrich and Jeffrey Wright. The film explores identity, allegiance, and the costs of guerrilla conflict through intimate skirmishes rather than large battlefield set pieces.

Shot on location with detailed period costuming and weaponry, the production recreates rural hideouts, winter encampments, and frontier towns. The narrative includes the Lawrence raid and its aftermath, using historical incidents to frame the characters’ choices. A folk influenced score and naturalistic cinematography complete the grounded tone.

‘Pawn Sacrifice’ (2014)

Edward Zwick’s biographical drama follows chess prodigy Bobby Fischer through his rise and the championship showdown with Boris Spassky. Maguire plays Fischer opposite Liev Schreiber’s Spassky, with Peter Sarsgaard as priest and coach William Lombardy. The film tracks Fischer’s preparation, the politics around the Reykjavik match, and the pressure created by Cold War attention.

The chess sequences use real positions drawn from documented games, with camera placements that turn quiet boards into tense arenas. Archival style interludes and crowd reactions give context for the global broadcast environment. Production design recreates hotel rooms, press halls, and practice spaces to show how isolation and scrutiny shaped the title character.

‘Brothers’ (2009)

Director Jim Sheridan remakes a noted Danish drama about a Marine officer who returns home after being presumed dead. Maguire plays the returning soldier, with Jake Gyllenhaal as his brother and Natalie Portman as his wife. The story examines trauma, family strain, and the difficulty of reintegrating into ordinary life after combat.

The film balances domestic scenes with flashbacks to captivity, pairing handheld intimacy at home with stark sequences abroad. Performances were recognized by awards bodies for their intensity and control. Production focused on neighborhoods, kitchens, and classrooms to underscore how stress radiates through a family and its routine.

‘The Great Gatsby’ (2013)

Baz Luhrmann adapts the classic F. Scott Fitzgerald novel with Maguire as narrator Nick Carraway. The cast includes Leonardo DiCaprio as Gatsby, Carey Mulligan as Daisy Buchanan, and Joel Edgerton as Tom Buchanan. The film frames Nick as both participant and observer, giving him voiceover duties that connect parties, confessions, and confrontations.

The production was staged at large sound facilities in Australia with digital cityscapes, lavish costumes, and elaborate party choreography. Contemporary music supervision, led by executive producer Jay Z, mixes with period elements to shape the film’s heightened mood. The 3D presentation and stylized editing emphasize spectacle while keeping the focal point on Nick’s perspective.

‘Wonder Boys’ (2000)

Curtis Hanson brings Michael Chabon’s novel to the screen with Maguire as student writer James Leer. Michael Douglas plays a blocked professor navigating a chaotic weekend that also involves Frances McDormand, Robert Downey Jr., and Katie Holmes. The story follows a manuscript gone astray, a literary festival, and a series of misadventures that reveal the characters’ creative and personal blind spots.

Pittsburgh locations provide wintry streets, campus offices, and houses packed with books and mementos. The film features an original song by Bob Dylan that drew major awards attention. Its tone comes from sharp dialogue and character driven scenes, giving Maguire space to play a talented but unreliable storyteller.

‘Seabiscuit’ (2003)

Gary Ross directs this adaptation of Laura Hillenbrand’s bestseller about the undersized racehorse that lifted spirits during the Great Depression. Maguire plays jockey Red Pollard alongside Jeff Bridges as owner Charles Howard and Chris Cooper as trainer Tom Smith. The film follows the partnership that turns a long shot into a champion through strategic training and daring rides.

Race sequences combine practical track work with visual effects to place viewers beside the saddle. The production used historic racing venues and period cars, clothing, and signage to recreate the era. The film received multiple Academy Award nominations, including recognition for Best Picture, cinematography, and sound.

‘The Ice Storm’ (1997)

Ang Lee adapts Rick Moody’s novel about two suburban Connecticut families during a turbulent holiday weekend. Maguire plays Paul Hood, away at college and circling a relationship with a classmate, while his parents and sister face their own crises at home. The ensemble includes Kevin Kline, Joan Allen, Sigourney Weaver, Christina Ricci, and Elijah Wood.

Production design meticulously evokes the fashions, interiors, and cultural references of the early seventies. The film premiered at major festivals and drew critical attention for its ensemble work and precise tone. Quiet scenes, sudden weather shifts, and carefully staged gatherings build an atmosphere that carries through to a stark conclusion.

‘Pleasantville’ (1998)

Gary Ross writes and directs this story of two modern teens who find themselves inside a black and white television sitcom. Maguire plays David, who becomes Bud in the show’s world, with Reese Witherspoon as his sister Jennifer. As characters begin to change, color appears inside monochrome frames, creating a visual language that tracks personal awakening.

The film blends practical effects with pioneering digital color processes to place grayscale figures beside saturated elements in the same shot. The ensemble includes Jeff Daniels, Joan Allen, and William H. Macy, with notable supporting turns that anchor the town’s shifting dynamics. The production earned Academy Award nominations for art direction, costume design, and original score.

Share your picks in the comments and let everyone know which Tobey Maguire movie you think deserves more attention.