In the years since he first stepped into the Spidey suit, Tobey Maguire has also become a recognized producer in Hollywood. On-screen, meanwhile, he has worked alongside the biggest names in Hollywood, from Charlize Theron (The Cider House Rules), Jake Gyllenhaal (someone he arguably looks like, so it's no surprise they teamed up for Brothers) and childhood best friend Leonardo DiCaprio (The Great Gatsby).
According to The Hollywood Reporter, Maguire sparked rumors of his retirement from acting when he established his own production company in 2012 called Material Pictures and co-produced Good People that same year. But in 2014, he produced Pawn Sacrifice and also starred in the film as chess icon Bobby Fischer. Most notably, Maguire returned to his iconic Spider-Man character in the MCU's Spider-Man: No Way Home, teaming up with both Tom Holland and Andrew Garfield's respective Spider-Man characters. What's more, Maguire's Spider-Man is rumored to cameo in the upcoming Doctor Strange in the Multiverse of Madness. In celebration of Maguire's recent return to the Spider-Verse, here's a closer look at his finest films to date.
5 The Ice Storm (1997)
It's suburban New Canaan, Connecticut. The year is 1973. Two middle-class families experimenting with casual sex and substance abuse come to find their lives beyond their control. The Ice Storm was released in 1997 courtesy of legendary filmmaker Ang Lee (Brokeback Mountain). It also features an extremely talented ensemble cast that includes Kevin Kline, Joan Allen, Christina Ricci, Elijah Wood, Katie Holmes, and Sigourney Weaver. Set during Thanksgiving, the plot finds the families dealing with tumultuous social changes of the early 1970s and the questionable forms of escapism as byproducts. Critical response to the film was positive, and the was selected to compete for the Palme d'Or at the Cannes Film Festival. Tobey Maguire plays Paul, a boarding school student who has a crush on Holmes' character. At a young age, he showed true signs of stardom with this smaller effort.
4 Seabiscuit (2003)
Based on an acclaimed book following the life and racing career of the eponymous champion thoroughbred racehorse, the 2003 sports drama Seabiscuit centers on the undersized and often overlooked horse whose unexpected success made him a widely popular media sensation during the Great Depression. Tobey Maguire appears as John “Red” Pollard, Seasbiscuit’s Canadian horse racing jockey, who forms a deep bond with the powerful animal while dealing with his own personal struggles with vision loss. The Gary Ross drama emphasizes just how important the unlikely champion Seabiscuit was to Americans during the difficult period of time, and how he became a symbol of hope to millions. "Other than being an exciting horse racing movie, it's also a movie about these broken down people who come together, become a family, and succeed together," Maguire told BBC during an interview amid the film's release.
3 Pleasantville (1998)
Leading up to his turn as Spider-Man, tobey Maguire played a kid obsessed with old sitcoms in Pleasantville. This 1998 Gary Ross classic centers on two siblings who are mysteriously transported inside a classic TV series set in an idyllic small town. In addition to Maguire and Reese Witherspoon (playing his sister), this unique tale also showcased the late Paul Walker's true potential as a leading man. It also stars Jeff Daniels, Joan Allen, William H. Macy and J. T. Walsh, which made for one of his final performances.
2 Spider-Man 2 (2004)
"Now this is what a superhero movie should be," reads the first sentence of Roger Ebert's four-star review of Sam Raimi's Spider-Man 2, the sequel to the 2002 mega-hit that changed superhero movies forever. In this story, Peter Parker is battling it out with a new villain named Doctor Octopus (Alfred Molina) while struggling to keep both his romantic life with Mary-Jane Watson (Kirsten Dunst) and friendship with Harry Osborne (James Franco) afloat. However, all that comes to a raging halt when, all of a sudden, Spidey loses his powers and begins to question his superhero status.
Marvel fans clearly cannot get enough of Maguire's Spider-Man as a new movement has been launched for Sony to finally develop Sam Raimi's Spider-Man 4. At one point in time, Raimi was planning to make the fourth movie with Tobey Maguire returning as Peter Parker. The sequel was shelved before production could begin, leading to the eventual reboots with Andrew Garfield and Tom Holland. The OG web-slinger is more popular than ever with the immense success of the newest film Spider-Man: No Way Home. The movie also blasted the doors wide open to revisit characters and storylines from previous film franchises, so why not entertain the notion of another Maguire turn as the beloved web slinger?
1 Spider-Man: No Way Home (2021)
By reprising his role in Spider-Man: No Way Home (2021), Maguire earned the Guinness World Record for "longest career as a live-action Marvel character." Showing that the rumors had been true all along, Maguire and Andrew Garfield both appeared in the 2021 film as their own respective Peter Parkers to team up with the MCU's Tom Holland. Those who had the privilege of seeing Spider-Man: No Way Home in theaters can surely attest to audiences erupting in celebration upon seeing Maguire appear is an understatement.
The film became an instant smash that has just continued to grow and grow despite being released during COVID-19 restrictions. The film has now become the sixth-biggest movie of all time and highest-grossing Spider-Man release of all time. And with the Academy honoring a "fan favorite" at this year's Oscars ceremony, it's looking more and more like No Way Home can walk away with the unique show of recognition.
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March 17, 2022
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Best Tobey Maguire Movies, Ranked - MovieWeb
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