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Tobey Maguire Then & Now: Photos of the Spider-Man Through the Years

By:
June 27, 2023 1:24PM EDT
©Columbia Pictures/Courtesy Everett Collection

Tobey Maguire shot to superstardom with ‘Spider-Man’. Check out photos of him from his early days to now!

Shooting straight to the top! Tobey Maguire was an unmistakable talent from the moment he stepped onto the stage as a teen, but it would be his roles in Sam Raimi’s ‘Spider-Man’ films that catapulted him into superstardom. Born in Santa Monica, California, he got into acting as a teen when his mom convinced him to take drama class instead of home economics.

Tobey would get his first role in 1989’s The Wizard and roles on TV’s Roseanne and Walker, Texas Ranger followed. It was in 2001 that Tobey earned the part of a lifetime when he was cast as Peter Parker AKA Spider-Man. He made 3 films as the web-slinger before hanging up his suit in 2007. Tobey would find critical acclaim with films like Pleasantville, The Cider House Rules, and Seabiscuit, for which he was nominated for a Screen Actors Guild Award in 2004.

Let’s take a look at Tobey through his career, from a teen actor to a comic book icon! Scroll through for more photos.

1 of 19

Tobey Maguire in ‘Great Scott’ (1992)

Tobey Maguire in ‘Great Scott’ (1992)
Fox-Tv/Kobal/Shutterstock

Tobey is book-smart in ‘Great Scott’ in 1992. The Fox sitcom followed a teen (Tobey) and his vivid imagination. It was short-lived, however, only running for 6 episodes. 

December 8, 2021, 4:17PM
2 of 19

Tobey Maguire & Michael Cane (1997)

Tobey Maguire & Michael Cane (1997)
Bei/Shutterstock

Michael Caine taps Tobey Maguire on the shoulder at the Miramax Pre Oscar Party on Mar. 23 1997. The duo would go on to work on ‘The Cider House Rules’ together.

December 8, 2021, 4:17PM
3 of 19

Tobey Maguire in ‘The Cider House Rules’ (1999)

Tobey Maguire in ‘The Cider House Rules’ (1999)
Moviestore/Shutterstock

Tobey played Homer Wells in ‘The Cider House Rules’. The movie — which was based on a 1985 John Irving novel — follows Tobey during the World War II–era. After being raised in Maine orphanage run by a doctor who trained him, he sets out on his own

December 8, 2021, 4:17PM
4 of 19

Tobey Maguire at Screen Actors Guild Awards (2000)

Tobey Maguire at Screen Actors Guild Awards (2000)
Araldo Di Crollalanza/Shuttersto

Tobey Maguire looks dapper at the Screen Actors Guild Awards in 2000. That year he and the cast of ‘The Cider House Rules’ were nominated for best dramatic ensemble.

The cast also featured Charlize Theron, Paul Rudd, and Erykah Badu. They lost to the cast of ‘American Beauty.’

December 8, 2021, 4:17PM
5 of 19

Tobey Maguire & Kirsten Dunst in ‘Spider-Man’ (2000)

Tobey Maguire & Kirsten Dunst in ‘Spider-Man’ (2000)
Moviestore/Shutterstock

Tobey and ‘Spider-Man’ co-star Kirsten Dunst demonstrate their chemistry. She played love interest Mary Jane Watson in the movies. The duo won the MTV Movie Award for Best Kiss in 2000. The real-life Tobey and Kirsten briefly dated between the first and second film, but stayed good friends.

Kirsten called Tobey the best Spider-Man in 2017 interview, where she told Marie Claire UK, “We made the best ones, so who cares? I’m like, ‘You make it all you want.'” Taking a dig at more recent Spider-Man films, she added, “They’re just milking that cow for money. It’s so obvious. You know what I mean?”

December 8, 2021, 4:17PM
6 of 19

Tobey Maguire out (2002)

Tobey Maguire out (2002)
Steve Levy/Shutterstock

Tobey Maguire visits the chiropractor in Santa Monica, California on Sep. 25 2002. Tobey reportedly suffered back problems after making ‘Seabiscuit’ in 2002. 

December 8, 2021, 4:17PM
7 of 19

Tobey Maguire in ‘Spider-Man 2) (2002)

Tobey Maguire in ‘Spider-Man 2) (2002)
Moviestore/Shutterstock

Tobey Maguire slings webs in ‘Spider-Man 2’. While the star reportedly made $4 million for the original, he’s said to have earned $17.5 million for the sequel. The film raked in $789 million internationally after spending a substantial $200 million.

Years later, co-star Kristen Dunst would complain about the pay disparity on set. She told The Independent in Nov. 2021, “The pay disparity between me and Spider-Man was very extreme. I didn’t even think about it. But you know who was on the cover of the second Spider-Man poster? Spider-Man and ME.” The star didn’t offer up specific numbers, however.

December 8, 2021, 4:17PM
8 of 19

Tobey Maguire at ‘The Good German’ (2006)

Tobey Maguire at ‘The Good German’ (2006)
Picture Perfect/Shutterstock

Tobey Maguire at ‘The Good German’ film premiere Dec. 4 2006. The Steven Soderbergh-directed film also featured A-listers George Clooney and Cate Blanchett. It is a murder mystery set in Berlin, Germany after the fall of the Nazi regime.

December 8, 2021, 4:17PM
9 of 19

Tobey Maguire, Jennifer Meyer & daughter (2008)

Tobey Maguire, Jennifer Meyer & daughter (2008)
London Entertainment/Shutterstoc

Tobey Maguire and wife Jennifer Meyer spend a Sunday afternoon hanging out in Coldwater Park in Beverly Hills, ca with their daughter Ruby in March 2008. The pair met while he was working on ‘Seabiscuit’ in 2003 and were engaged in 2006. They wed in Hawaii on Sept. 3 2007 and daughter Ruby was born two months later. The couple would welcome a son Otis in 2009. 

The relationship had run its course by 2016, when the pair announced they were separating. Jennifer waited until Oct. 2020 to officially file divorce papers.

The former pair are still on great terms. Jennifer opened up about their friendship to Us Weekly in 2018. She said, “He’s my best friend…He’s the greatest ex-husband a girl could ever have”.

December 8, 2021, 4:16PM
10 of 19

Tobey Maguire in ‘Brothers’ (2009)

Tobey Maguire in ‘Brothers’ (2009)
Palomar/Kobal/Shutterstock

Tobey Maguire looks on in ‘Brothers’. The film also starred Jake Gyllenhaal and Natalie Portman. In ‘Brothers’, an adaptation of a Danish film, Tobey plays a soldier and former P.O.W. who has to grapple with PTSD as he reintegrates into society. He was praised for his performance and even earned a Golden Globe nomination.

December 8, 2021, 4:16PM
11 of 19

Tobey Maguire at ‘Country Strong’ (2010)

Tobey Maguire at ‘Country Strong’ (2010)
Charles Sykes/Shutterstock

Tobey Maguire shines at the ‘Country Strong’ premiere in Nashville, Tennessee on Nov. 8 2010. He produced the movie, which was written and directed by Shana Feste. Shana came up with the story while working as a nanny for Tobey. ‘Country Strong’ starred Gwyneth Paltrow, Tim McGraw, Garrett Hedlund, and Leighton Meester.

December 8, 2021, 4:16PM
12 of 19

Tobey Maguire at Spike TV’s Guys Choice Awards (2012)

Tobey Maguire at Spike TV’s Guys Choice Awards (2012)
Matt Sayles/Invision/AP/Shutters

Tobey Maguire presents an award onstage at Spike TV’s 2012 Guys Choice Awards in Culver City, California. He was a presenter.

December 8, 2021, 4:16PM
13 of 19

Leonardo DiCaprio & Tobey Maguire promote ‘The Great Gatsby’ (2013)

Leonardo DiCaprio & Tobey Maguire promote ‘The Great Gatsby’ (2013)
Victoria Will/Invision/AP/Shutte

Leonardo DiCaprio and Tobey Maguire pose for a portrait to promote ‘The Great Gatsby’. The pair met while competing for roles in the early 90s but fast became friends.

Leo even remembered the moment they met, telling Esquire in 2014 how his mom was driving him when he saw Tobey on the street “I literally jumped out of the car. I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah — I know you. You’re . . . that guy.’ But I just made him my pal. When I want someone to be my friend, I just make them my friend.”

Tobey told People about their friendship in 2013, calling them “like any other buddies”. He went on, “There’s a lot of laughing and chatting between us. We enjoy doing a lot of things we have in common, like basketball. We like to play and talk about basketball.”

December 8, 2021, 4:16PM
14 of 19

Tobey Maguire at ‘Pawn Sacrifice’ (2014)

Tobey Maguire at ‘Pawn Sacrifice’ (2014)
Broadimage/Shutterstock

Tobey Maguire is handsome at the ‘Pawn Sacrifice’ film premiere on Sep. 11 2014. The biographical drama film was about chess player Bobby Fischer and his battle against the top Soviet players during the Cold War. Though the movie earned positive reviews, it only took in $19 million at the box office.

December 8, 2021, 4:16PM
15 of 19

Tobey Maguire at Fox Golden Globes Party (2016)

Tobey Maguire at Fox Golden Globes Party (2016)
Eric Charbonneau/Shutterstock

Tobey Maguire watches on at FOX’s Golden Globes Party on Jan. 10 2016. At the awards show, he introduced BFF Leonardo DiCaprio’s Best Motion Picture – Drama entry, The Revenant. The film ended up winning and would later take top honors at that year’s Oscars.

December 8, 2021, 4:16PM
16 of 19

Tobey Maguire out in LA (2018)

Tobey Maguire out in LA (2018)
Broadimage/Shutterstock

Tobey Maguire runs errands in LA on Valentine’s Day 2018. In recent years, he’s pivoted from acting to producing. Talking about his behind-the-scene ambitions with The Hollywood Reporter in 2019, he laughed, “Have I retired? I’ll do what I feel called to do. I suspect I’ll be excited when I do it. Like, just whenever the calling appears, I guess.”

December 8, 2021, 4:16PM
17 of 19

Tobey Maguire & Tatiana Dieteman (2019)

Tobey Maguire & Tatiana Dieteman (2019)
Todd Williamson/January Images/S

Tatiana Dieteman wraps an arm around boyfriend Tobey Maguire at the premiere of ‘Brittany Runs A Marathon’ on Aug. 15 2019. Tobey was one of the film’s producers.

Tobey and Tatiana, who are 14 years apart, started seeing each other in 2018. They reportedly met at a party hosted by Leonardo DiCaprio.

December 8, 2021, 4:16PM
18 of 19

Tobey Maguire & Tatiana Dieteman (2020)

Tobey Maguire & Tatiana Dieteman (2020)
Shutterstock

Tobey Maguire and Tatiana Dieteman take a stroll on May 10 2020. Tatiana is said to have a strong relationship with Tobey’s kids and his ex Jennifer Meyer. “Tatiana and Tobey’s ex-wife Jen get along well,” an insider told Us Weekly in 2020. “Tobey’s kids love [Tatiana]… She’s great with them.”

December 8, 2021, 4:16PM
19 of 19

Tobey Maguire & His Daughter Ruby At ‘Babylon’ Premiere

Tobey Maguire & His Daughter Ruby At ‘Babylon’ Premiere
GilbertFlores@Broadimage / MEGA

Tobey Maguire brought his daughter Ruby to the premiere of his latest movie ‘Babylon’ in December 2022. The movie marks Tobey’s third role in 8 years, since starring in the 2014 biopic ‘Pawn Sacrifice.’

December 16, 2022, 8:39AM