TOBEY MAGUIRE - MY LIFE IN 10 Pictures

BORN IN Santa Monica, California, Tobey Vincent Maguire grew up, as he told The Guardian, “very poor.

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I always had a roof over my head, but I slept on couches of relatives, and some nights we wandered into a shelter. I wanted to get out of that, so my ambition was initially to make money; I was pretty driven.” When his mom managed to save $100, she found the perfect avenue for that drive by enrolling him in a drama class. “My mom wanted me to be an actor. She thought I was creative and sensitive,” he told Acting Magazine. “That was probably the best $100 [she] ever spent.” And who could argue? Tobey has created one of the most diverse Hollywood resumes — including, of course, four turns as Spider-Man. Yet, as he celebrates a milestone 50th birthday on June 27, Tobey is as happy to spend time with daughter Ruby and her younger brother Otis as he is acting. He's far from complacent, though. As Tobey told Nylon, “I’m very eager and excited to find new challenges. And I don’t know exactly what that looks like, but I like the unknown.”

1. 1993 DRIVING FORCE

On This Boy's Life, Tobey found a lifelong friend in Leonardo DiCaprio (back right). "We're both really competitive," he said. "I think we have a lot of confidence in our own individual paths, so whether it's with each other or with other friends of ours, we root for them. We're fans of our greatest competitors. We can joke with each other about competition, but are supportive. I have a whole bunch of friends like that."

2. 1997 TAKEN BY STORM