Tobey Maguire

With parents who divorced while he was still young, Maguire spent a lot of his early years between his father’s house in Washington, and his mother’s house in California.

It was his mother who first encouraged him to take up acting, and it was thanks to her persistence (and her ferrying him to and from auditions) that he got his first on-screen role – a one-liner in the sitcom Roseanne.

This was soon followed by two lines in Blossom – and buoyed by this success, Tobey dropped out of high school at the end of the ninth grade,
determined to devote his time to acting.

A number of near misses followed: Maguire was cast as the lead in the 1992 Fox series ‘Great Scott’, about a high school freshman and his overactive imagination – but it was cancelled after just 9 weeks. In 1995 he tried for the lead role in Empire Records, but was given only a small part – which he eventually walked away from.

In 1996 Tobey starred in ‘Duke of Groove’ – a short film that was later nominated for an Oscar. The attention he gained led to a part in Woody Allen’s 1997 film ‘Deconstructing Harry’, and Ang Lee’s ‘The Ice Storm’ the same year. Maguire was finally established – and a string of other roles came his way.

His breakout hit came in the form of 2002’s Spider-Man – a role that he was paid a massive $4million for. Just as Peter Parker made the transition from awkward teen to web-spinning superhero, Maguire made the transition from jobbing actor to Hollywood royalty.

Underground Poker


Like so many other movie stars, Tobey Maguire is a casino fan – known for his love of high-stakes poker. Although according to Molly Bloom, who used to organise underground poker games for Hollywood’s richest players, while he’s a great player “he’s a sore loser. And a worse tipper”.

According to Bloom, Maguire once asked her to bark in return for a $1,000 tip. She understandably refused. Bloom used to refer to Maguire as Hannibal Lecter “because he could just talk someone off of a good hand”.

In 2011 Tobey Maguire was one of a number of high-stakes players sued by investors in a Ponzi scheme run by convicted fraudster Bradley Ruderman. Ruderman had paid Maguire a poker debt of $311,000 using money he’d stolen via the scheme. Maguire settled out of court, paying $80,000 to each of Ruderman’s former victims.