1989–1995: Early career Maguire's first appearance in a feature film was as an extra in
The Wizard (1989). He was cast as the lead in the FOX TV series
Great Scott! in 1992, which was canceled nine weeks after its premiere. Maguire met fellow child actor
Leonardo DiCaprio in the 1980s while auditioning for the same roles. The pair became close friends. They both auditioned for the same part in the
1990 TV series based on the 1989 comedy
Parenthood. DiCaprio got the part, and Maguire was cast in a guest role partly on DiCaprio's recommendation. The same scenario played out during casting for the 1993 movie ''
This Boy's Life'' (featuring
Robert De Niro as the lead): DiCaprio got the main role of teenager Tobias "Toby" Wolff, while Maguire was cast as one of his friends.
1995–2001: Critical acclaim As part of his recovery from alcoholism and learning to deal with his self-described "addictive and compulsive nature", Maguire changed his career path slightly to seek roles that would not put him in direct competition with DiCaprio. The move paid off when Maguire was cast as Paul Hood (a teenage boarding school student whose narration anchors the action) in
Ang Lee's 1997 film
The Ice Storm. This led to a variety of lead roles in films, such as
Pleasantville,
The Cider House Rules, and
Wonder Boys. In the 1998 film
Fear and Loathing in Las Vegas Maguire portrayed a hitchhiker who meets
Raoul Duke and
Dr. Gonzo during their drive to Las Vegas. In
Ride with the Devil (1999), opposite
Jewel Kilcher, Maguire portrayed Jakob Roedel, the son of a unionist German immigrant who joins his Southern friends in the Missouri Riders, avenging the atrocities committed against Missourians by Kansas
Jayhawkers and redleggers. Maguire voiced Lou in the movie
Cats & Dogs (2001).
2002–2013: Spider-Man and stardom In 2002, Maguire starred as the
title character in
Spider-Man, based on the
Marvel Comics superhero of the same name. The film was a major success and made him a star. His performance as Spider-Man earned him glowing reviews. Mark Caro of the
Chicago Tribune wrote that, "with his big, round, soulful eyes, Maguire always has been able to convey a sense of wonder, and his instinct for understatement also serves him well here." That same year, he was credited as a producer on the film
25th Hour, and the next year, on
Whatever We Do. Maguire had a lead role as the
jockey John M. "Red" Pollard in
Seabiscuit (2003), based on
Laura Hillenbrand's
novel of the same name about the famous
racehorse Seabiscuit. In addition to acting, he was also credited as an executive producer. In 2004, he reprised his role as Peter Parker in
Spider-Man 2, which, like its predecessor, was a critical and commercial hit and is often considered to be one of the best superhero movies of all time. Due to the physical toll of filming
Seabiscuit, Maguire was often absent from the set of
Spider-Man 2; he was nearly fired and his role was offered to
Jake Gyllenhaal. However, his girlfriend's father
Ronald Meyer was able to help him secure the role. Maguire admitted his behavior toward the situation was "inappropriate" and that he learned his lesson. Gyllenhaal would later make his Spider-Man debut as
Mysterio in 2019's
Spider-Man: Far From Home. He next played Spider-Man in
Spider-Man 3 (2007). The film was a box office hit, but received mixed reviews, with critics praising the cast and visual effects but criticizing the overabundance of villains. Plans for
Spider-Man 4 were set in order, but despite the proposed addition of characters like the
Vulture and
Black Cat (with
John Malkovich and
Anne Hathaway in talks to play them), the film was ultimately cancelled due to director
Sam Raimi feeling creatively constrained, the poor reception to the previous film, and script and production complications.
Sony's
Columbia Pictures decided to
reboot the franchise instead. The series was cancelled due to these factors, as well as a desire to integrate Spider-Man into the
Marvel Cinematic Universe. In 2008, he made a
cameo appearance in the
action comedy film Tropic Thunder as a
gay 18th century monk in love with Father O'Malley, played by
Robert Downey Jr., in the faux trailer for ''Satan's Alley
. He was a last-minute replacement in the role, and due to previously scheduled commitments was only available to be on set for two hours to film his scenes. Near the end of Tropic Thunder'', it is revealed that Maguire's character has been nominated for the
Academy Award for Best Actor for ''Satan's Alley
, which he loses to Tugg Speedman (Ben Stiller) for his role in Tropic Blunder'', presented by Kirk Lazarus. In 2009, Maguire starred alongside Gyllenhaal and
Natalie Portman in the
Jim Sheridan-directed war drama
Brothers as Sam Cahill, a prisoner of war who returns from
Afghanistan and starts suspecting that his wife has become romantically involved with his brother. He received critical acclaim and a
Golden Globe nomination for his performance in the film. Of the nomination, Maguire said, "I had no expectation about getting a nomination, but I was watching nonetheless. My wife and my son got really excited. I was sort of surprised – I was like, 'Oh, wow.' And I couldn't hear the latter part of my name." Maguire lost to
Jeff Bridges for his role in
Crazy Heart. Maguire was set to star as The Writer in
Life of Pi (2012), directed by
Ang Lee, but was cut from the film during production for being "too famous" compared to the rest of the cast. He was replaced by
Rafe Spall, with whom Lee reshot the scenes that had already been shot with Maguire. , 2013In 2012, Maguire was a co-producer of
Good People. That same year, he also established his own production company, Material Pictures, which secured independent financing in 2013 to help it produce more feature films. Maguire and DiCaprio once again performed together in
Baz Luhrmann's remake of
The Great Gatsby (2013); DiCaprio played the
title role, while Maguire played the story's narrator,
Nick Carraway.
2014–present: Reduced output His next film,
Pawn Sacrifice (2014), was also co-produced by Material Pictures. It was a
Cold War thriller based on the true story of American chess prodigy
Bobby Fischer, played by Maguire. The film details the events leading up to and including the world chess championship in 1972, when Fischer challenges Soviet chess
grandmaster and world champion
Boris Spassky, acted by
Liev Schreiber. The film received mostly positive reviews, but greatly underperformed at the box office. Maguire voiced the adult version of Tim Templeton in the animated film
The Boss Baby (2017), reuniting with
Alec Baldwin after they previously collaborated in
Cats & Dogs (2001). Maguire also reprised his role as Spider-Man in the
Marvel Cinematic Universe film
Spider-Man: No Way Home (2021) alongside successors
Tom Holland and Garfield. The film was a critical and commercial success,
grossing over 1 billion dollars, the first
pandemic-era film to do so and the first since 2019's
Star Wars: The Rise of Skywalker. He appeared in
Damien Chazelle's
ensemble film Babylon, also serving as an executive producer. He reprised his role as Spider-Man in
Spider-Man: Across the Spider-Verse through archive footage. ==Personal life==