Tobey Maguires Disappearance: Chasing Youth and Poker

For , 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  or , the fear with Maguire is that his reputation for being difficult to work with, coupled with his apparent penchant for , 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  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 found fame with the Spider-Man trilogy in 2007 and won an Oscar nomination for his role as a jockey in Seabiscuit - but with fame came talk of him being difficult to work with