The disappearance of Tobey Maguire: Actor's sad decline in Leonardo DiCaprio's 'shadow' - and new life chasing decades-younger models and poker games

For Tobey Maguire, acting has always been a 'continuous challenge' to find something that he feels is his calling - an opportunity to 'blow it out,' as he once described it.

But after decades of searching, Maguire, 50, seems done with the interminable waiting game.

An elusive presence in Hollywood he may be, but even by his standards, eight film credits in close to 20 years screams of a man who has grown disinterested.

Although not unusual for an actor to take time out or quietly transition behind the camera, à la Joseph Gordon-Levitt or Ashton Kutcher, the fear with Maguire is that his reputation for being difficult to work with, coupled with his apparent penchant for hanging out with younger women, might have started to work against him.

'It doesn't feel like Tobey has that same determination he did over a decade ago, which is really unfortunate,' an insider exclusively told the Daily Mail. 

They claimed his only hope of landing 'big roles' in the future could be if 'he has help from his friends who want him in their movies,' adding: 'That's just how it is and it's not going to change unless he gets his act together. He doesn't seem to take acting as seriously anymore and those in his inner circle know it.'

After all it was his best pal Leonardo DiCaprio, 51, who helped give him a leg up in films including Parenthood and This Boy's Life when they were fledgling actors desperate to make it in the early 1990s.

But our insider suggested that where DiCaprio has managed to juggle his reputation for partying with climbing the ladder in Hollywood, recently landing his eighth Oscar nomination for his role as a washed-up revolutionary in Paul Thomas Anderson's One Battle After Another, Maguire has seemingly struggled, with few projects of late to distract from his antics. 

Maguire was previously married to Jennifer Meyer, whose father Ronald was vice chairman of NBCUniversal and reportedly helped to smooth over a squabble he had with Sony, more on that later. The couple, who have children Ruby, 19, and Otis, 16, called it quits in October 2016 after nine years of marriage and 'much soul searching and consideration.' Their divorce was finalized in 2021. 

He was then linked to Babette Strijbos in summer 2024, when the pair was pictured kissing. She was 24 at the time.

In the years since, he has been pictured out with younger women, controversially the now 22-year-old influencer Lily Chee at a star-stuffed Hamptons White Party back in summer 2024. It catapulted her into the spotlight but wrought suspicion on Maguire for he was 49 at the time, while Chee was a 20-year-old student (close in age to Maguire's daughter, who was then 17). 

Amid the brouhaha, Meyer defended him, insisting her ex was 'as good of a guy as it gets.'

Then, last month a TMZ video showed him scaling a wall with a woman who online sleuths are convinced was Chee. The frenzy was further fueled days later when he was pictured with 20-year-old Internet personality Mishka Silva at the Super Bowl.    

'Tobey is like Leo's twin,' our insider said. 'The difference is Leo is this megastar and Tobey lives in his shadow. Leo is Hollywood's heartthrob, Academy Award winner and Tobey is basically his bestie who people keep forgetting about until they're seen together.'

'He's a professional actor and will always be known for playing Spider-Man, but then there's also this wild side to him. He's a big partier, loves partying with models, hangs out with younger women... and bad influences,' the source added.

'He's not like going to hit rock bottom but if he wants to be known for his acting again, then he should get cleaned up.' 

Born in 1975 in Santa Monica to teenage secretary Wendy Brown and cook-turned-part time construction worker Vincent Maguire, the bright lights of Hollywood may have been within reach – but Maguire's was a life so far removed from those living the Hollywood dream less than 30 miles away.

Instead, his was a peripatetic existence, sofa-hopping at different relatives, living in shelters, and collecting food stamps after his parents' short-lived marriage crumbled when he was just three years old.

His transient existence saw him drop out of school in ninth grade and he battled substance abuse and alcohol dependency. He had plans to follow his father and become a cook, but adamant her son has a better life, his mother offered him $100 to take an acting class over home economics.

And so began his path out of poverty.

His was the long-trodden route of wannabe actors – bit roles in commercials (Atari Lynx, Doritos and Tropicana Twister) and playing extras (General Hospital, Roseanne). His first feature film appearance was in The Wizard in 1989.

Three years later, age 17, he had finally landed his first lead role in Fox comedy Great Scott! – only for it to be scrapped abruptly in the US after six episodes less than one month after it debuted.

Thankfully, momentum started building after he was cast in Ang Lee's The Ice Storm in 1997 with roles in Pleasantville, The Cider House Rules and Wonder Boys following in quick succession.

Then in 2002 he landed the role of his life, playing the titular superhero in Spider-Man. The film – famous for Maguire's upside-down kiss with costar Kirsten Dunst – grossed $826 million against its $139 million budget at the box office. Maguire had finally made it.

But stardom was complicated.

The California-native, who is now worth an estimated $75 million, was plagued by rumblings of being difficult to work with. 

While unsubstantiated rumors run wild on sites like Reddit, Charlize Theron did previously hint at tensions, claiming they had a 'bit of a rough time' working on The Cider House Rules, while James Franco also claimed that Maguire was 'mad at me for a while' on the set of Spider-Man.

Sony execs clearly struggled too, having reportedly accused Maguire of trying to play hardball with the studio during contract negotiations for Spider-Man 2.

So the snafu went: Maguire sustained a back injury while filming Sea Biscuit in 2002. As a result, his agents claimed he wouldn't be able to do all of the web-slinging stunts required on his return to the Spider-Man universe months later. Studio brass took this as a threat to squeeze them for more money, and it was reported that Jake Gyllenhaal was secretly lined up as a replacement. 

Eventually all was resolved and Maguire went on to reprise the role again for the final trilogy instalment in 2007 and once more in Spider-Man: No Way Home in 2021. He is rumored to be returning for Avengers: Doomsday.

Unlike his former costars Dunst and DiCaprio, and his Spider-Man successor Andrew Garfield – who all went on to scale the upper echelons of Hollywood – Maguire's credits have been sparing, with only eight film roles since 2007. Although, he has produced a smattering of films via Material Pictures, the production company he founded in 2012.

Instead, Maguire was making millions playing underground poker, famously taking part in high-stake games at The Viper Room hosted by Molly Bloom, who described the actor as 'the worst tipper, the best player, and the absolute worst loser.' He later found himself having to pay $80,000 to settle a lawsuit over what a judge alleged were unlicensed games in 2011.

'Some people like playing golf with their buddies – for Tobey he loves playing poker,' said a second insider. 'He's won an earth-shattering amount of money, and he is stubborn when it comes to poker – he doesn't want to stop. That takes a bunch of his time, and when he isn't doing that, he will focus on work.'

So, is Maguire worried his 'wild side' will to impact his reputation as a leading Hollywood star?

'There have been rumors that he was difficult to work with in the past, but no one really sees that as being a thing,' the insider said. 'He might not be the first choice, but he does get scripts sent his way, and he will end up doing something if it is something amazing. He isn't just going to do something to collect a paycheck.

'When it comes to being seen with various girls, it's just not something he gets upset about.'