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.
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.
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.
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.
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.
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.
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.
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.
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.
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 yelling about professional wrestling to his wife. If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.