Trivia

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.

Close friend of Leonardo DiCaprio

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 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.

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

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

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.

Became a father for the 1st time at age 31 when his girlfriend [now wife], Jennifer Meyer, gave birth to their daughter, Ruby Sweetheart Maguire, on November 10, 2006.

Married Jennifer Meyer in a secret ceremony on Hawaii. The wedding was only attended by close friends [September 3, 2007].

Two of his half brothers make a cameo appearance as the two boys who gives him his mask in the train scene in Spider-Man 2.

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

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.

Was engaged to Rashida Jones (2002).

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

Became a father for the 2nd time at age 33 when his wife, Jennifer Meyer, gave birth to their son, Otis Tobias Maguire, on May 8, 2009.

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

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

Has been a vegan/vegetarian since 1992 and was voted the world's sexiest vegetarian by PETA, 2002.

He was considered for the role of Norman Bates in Psycho (1998) before Vince Vaughn was cast.

Friends with Spider-Man co-stars: Bryce Dallas Howard, Topher Grace and Rosemary Harris.

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 Van Epp (born 1991), and Weston Epp (born 1994).

His ancestry is English, Irish, German, Austrian, one eighth Puerto Rican, one eighth Polish, as well as more distant Danish, French, and Cornish. His maternal grandmother was born in Cape Town, South Africa, to an English family, and came to the U.S. in 1933.

He and Jennifer Meyer announced their engagement after the birth of their daughter Ruby Sweetheart.

Made his movie debut in This Boy's Life (1993).

Member of the AAs

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).

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

Was in attendance at the wedding of Reese Witherspoon to Jim Toth (26 March 2011).

He and his wife are very close friends of Sara Gilbert.

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

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.

Played 2 characters with the last name "Parker". Bud Parker in "Pleasantville" and Peter Parker in the "Spider Man" trilogy.

Son-in-law of Ron Meyer.

Close friends with Kevin Connolly.

As of 2022, he has appeared in two films that were nominated for the Best Picture Oscar: The Cider House Rules (1999) and Seabiscuit (2003).

Is closely associated with the likes of Robert Pattinson, Terry McGinnis and Leonardo DiCaprio working on several projects and conservationist initiatives together.

Filming Spider-Man 3 (2007) in New York. (June 2006)

Both Brad Pitt and Margot Robbie read Damien Chazelle's script for Babylon (2022) while filming Once Upon a Time in Hollywood (2019). DiCaprio's friend Tobey Maguire is one of the producers of Babylon.