Tobey Maguire has been working as an actor in Hollywood for more than thirty years. He got his start when he was just a teenager, appearing in small roles in films and on television. He became quite a successful and well-known actor by the mid-1990s, playing lead role in films like Pleasantville, The Cider House Rules, and Ride with the Devil.

His big break, however, came in 2003, when he was cast in the titular role of Sam Raimi's Spider-Man. Spider-Man was a major box-office success, and it rocketed Maguire to super-stardom.

Related: How Tom Holland, Tobey Maguire And Andrew Garfield Really Felt About Each Other Before And After Spider-Man: No Way Home

However, as Maguire became more and more successful, he also started to develop a reputation of being difficult to work with. While some of the stories about Maguire's attitude are simply unsubstantiated rumors, many others have a good deal of truth to them. Here is everything there is to know about why Tobey Maguire has a reputation of being difficult to work with.

8 Tobey Maguire's Friendship With Leonardo DiCaprio

Leonardo DiCaprio at a premier
Via: Instar

Tobey Maguire became friends with Leonardo DiCaprio in the 1990s when their careers were both starting to take off. They frequently found themselves competing for the same roles, and they struck up a friendship. They eventually formed a group of young male actors known for their partying lifestyle and constant pursuit of women. There have been numerous stories released about the group getting into fights and treating others with disrespect. While no specific allegations have come out about Tobey Maguire's behavior as part of that group, being a member of the group certainly harmed his reputation.

7 Tobey Maguire And Leonardo DiCaprio Starred In 'Don's Plum'

Spider-Man 2
Via instar

Several of the young men in Tobey Maguire's friend group, including Leonardo DiCaprio, created and acted in a film together called Don's Plum. Shortly after making the film – in which much of the dialogue was improvised by Maguire and DiCaprio – the actors tried to sue the movie studio to prevent it from being released. That lawsuit gave Maguire and DiCaprio a bad reputation among film producers, and the movie itself harmed their reputation among fans, many of whom criticized the misogynistic dialogue.

Related: Emma Stone Called Her Kissing Scene With Andrew Garfield In Spider-Man 2 "Icky," But Was It Better Than Her Experience With Ryan Gosling?

6 Tobey Maguire Didn't Get Along With Charlize Theron While Filming 'The Cider House Rules'

Tobey Maguire smiling at Babylon premiere
via instar

One of the movies that made Tobey Maguire into a household name was The Cider House Rules, in which he played the main character, Homer Wells. Unfortunately, he apparently did not get along well with the film's other star, Academy Award-winner Charlize Theron. Theron told V Magazine, "Tobey and I had a bit of a rough time... It was a difficult movie."

However, in the same interview Theron also explained that her and Maguire are on very good terms now, and that there were only a few days on set when they didn't get along. "We’re good now," she explained, and she later added, "I love Tobey."

5 Did Tobey Maguire Cause Drama Behind The Scenes of 'Spider-Man'?

Dunst and Maguire
Instar

There are stories about Tobey Maguire behaving like a "diva" behind the scenes of the Spider-Man movies, but not all of those stories have a basis in fact. For instance, there are rumors that Maguire did not get along with his Spider-Man co-stars, but none of his co-stars from the series have ever publicly said a bad word about Maguire. There has also been lots of speculation that Maguire behaved irresponsibly during his contract negotiations for Spider-Man 2, but those also seem to be nothing more than rumors. Certain sources suggested that Maguire faked a back injury in order to demand more money for Spider-Man 2, but director Sam Raimi clarified that Maguire did not fake his injury and that he did not lie during contract negotiations.

4 Tobey Maguire's Fraught Relationship With The Paparazzi

Tobey Maguire avoiding paparazzi
via instar

There have been a few instances over the years in which Tobey Maguire has faced criticism for getting into fights with the paparazzi. In one notable instance, he was filmed yelling and cursing at several photographers, and some of the pictures they took of him yelling were turned into popular internet memes. However, as Maguire explains in the video, he was simply upset because he felt that the paparazzi were endangering him while he tried to drive his car.

3 Was Michael Cera's Character In 'Molly's Game' Was Inspired By Tobey Maguire?

Tobey Maguire in suit at Babylon premiere
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Molly's Game is a film that came out in 2017, based on the memoirs of Molly Bloom. One of the characters in the film, played by Michael Cera, is believed to be based on several celebrity gamblers, including Leonardo DiCaprio and Tobey Maguire. The character is portrayed as an extremely unpleasant man, and that lead to questions about Maguire's real-life behaviour. The book that the film is based on is even more direct, and the author made it clear that Tobey Maguire was very difficult to work with while he was playing poker.

2 What Was The Parody Article About Tobey Maguire That Too Many People Believed?

Tobey Maguire, Michael Arndt, and Kirsten Dunst at the Oscars
Via: Instar

In 2015, the popular satire website Clickhole published an article called "6 Times Tobey Maguire Had A Public Meltdown Because Nobody Would Call Him ‘Tugboat Maguire.’" The article is a work of comedy and is not based in fact, but several sources seem to have taken it too seriously. This article from Hayvine uses quotations from the Clickhole article as if they are factual, while this article from Showbiz CheatSheet acknowledges that the article is satirical but still suggests that it is based in some truth. However, Tobey Maguire is not known for his "public meltdowns" as the article suggests, and the image the article uses is from the time Maguire yelled at paparazzi because he felt he was being harassed and endangered.

1 Tobey Maguire's Return To Spider-Man

close-up of Tobey Maguire at the Cannes Film Festival
via instar

In late 2021, Tobey Maguire returned to the Spider-Man franchise after fourteen years, and he reprised his role as Peter Parker in Spider-Man: No Way Home alongside Tom Holland and Andrew Garfield – who both also played Peter Parker. All three Peter Parker actors seem to get along with one another splendidly, and Tobey Maguire has nothing but good things to say about his fellow Spider-Men. He told Deadline, "I’m a big fan of Tom and those movies and Andrew." Garfield and Holland had similarly nice things to say about Maguire.

Garfield said he wouldn't have done No Way Home if Maguire wasn't involved, and when the film finally came out, the two of them went to see it together. In an interview with BBC Radio 1, Tom Holland shared that he's been "getting closer" with Maguire over the years, and that the three Peter Parker actors even have a WhatsApp group chat! So, by all accounts, Tobey Maguire was a pleasure to work with on the set of Spider-Man: No Way Home, perhaps putting to rest the rumors that he was an on-set diva during his original Spider-Man days.