Is good friends with his Spider-Man (2002), Spider-Man 2 (2004), and Spider-Man 3 (2007) co-star Kirsten Dunst.

Has four half brothers: 2 on his dad's side: Vincent Jr. (born 1973) and Timothy (born 1984); and two on his mother's side: Jopaul Epp (born 1991), and Weston Epp (born 1994).

Considered for the role of Will Turner in Pirates of the Caribbean: The Curse of the Black Pearl (2003).

Was engaged to Rashida Jones (2002).

Member of the AAs

He was originally set to play the role of Jake Hoyt in Training Day (2001), opposite Denzel Washington. He had even gone through two months of training with narcotic officers, weapons training, and put on a lot of muscle but the role was later given to the producer's first choice, Ethan Hawke, and Tobey went on to star in Spider-Man (2002) instead.

Almost couldn't do Spider-Man 2 (2004) after having severe back pains at the end of shooting Seabiscuit (2003), Jake Gyllenhaal was already in talks to replace him and had already begun preparation.

He played in the World Series of Poker. On October 27, 2004, he won the Phil Hellmuth Poker Invitational at the Hollywood Park Casino in Los Angeles, taking a first prize of $95,480.

Tobey and his fiancée, Jennifer Meyer, are the parents of a girl, Ruby Sweetheart Maguire, born at Cedars Sinai Medical Center in Los Angeles on November 11, 2006.

Is a vegan/vegetarian.

Often portrays heroes that are close to animals or creatures. In Cats & Dogs (2001), he provided the voice of Lou the Beagle in which he saves the world from cats; in Spider-Man (2002), he was bitten by a radioactive (genetically modified in the movies) spider that gave him superhuman abilities; in Seabiscuit (2003), he played Red Pollard, a jockey who rode a winning horse to victory.

Was originally cast as Alex Chance Browning in Final Destination (2000).

During the Australian release period of Spider-Man (2002), he appeared on an Australian late-night variety show with his co-star Willem Dafoe. During this interview, when asked if he was a fan of the comic book, he claimed that he had never touched a Spider-Man comic book before and that he never wanted to read them.

May, 2002: Bought a $3.5 million Beverly Hills mansion with his Spider-Man (2002) earnings.

He and his fiancée, Jennifer Meyer, announced their engagement in April. Jennifer is a jewelry designer [June 12, 2006].

While promoting The Good German (2006) on "The Tonight Show with Jay Leno" (1992), he revealed the baby's name, Ruby Sweetheart.

He and his best friend, Leonardo DiCaprio, were both in movie directed by Sam Raimi. DiCaprio was in The Quick and the Dead (1995) and Tobey was in Spider-Man (2002), Spider-Man 2 (2004) and Spider-Man 3 (2007).

Married Jennifer Meyer in a secret ceremony on Hawaii. The wedding was only attended by close friends.

He and his wife are very close to Sara Gilbert.

Tobey and his fiancée, Jennifer Meyer, are the parents of a girl, Ruby Sweetheart Maguire, born at Cedars Sinai Medical Center in Los Angeles on November 10, 2006.

Close friend of Leonardo DiCaprio

Enjoys playing chess.

Lost 25 pounds to fit his role as Red Pollard in Seabiscuit (2003).

Packed on several pounds to fit his role in Spider-Man (2002).

He will get $26 million for the two sequels to Spider-Man (2002).

Originally wanted to be a chef, but he turned to acting after his mother offered him $100 to take drama rather than home economics in high school.

Enjoys yoga and cooking.

Has been a vegan/vegetarian since 1992.