Before he donned the infamous Spider-Man costume, Tobey Maguire earned a reputation throughout Hollywood as a young actor who could effortlessly portray society’s outcasts. Maguire undertook a multitude of such roles, ranging from the teenage boy nostalgic for a time that never was in “Pleasantville” to the estranged but promising novelist in “Wonder Boys.”

Unlike many of his fellow young actors, Maguire was reluctant to take on roles that would guarantee him Hollywood success and the adoration of millions of teenage girls. Instead, he continued to challenge himself and his acting abilities by undertaking unique roles in smaller-budgeted films, such as Ang Lee’s “The Ice Storm.”

Maguire’s uncanny ability to convey the outsider mentality caught the attention of the producers of “Spider-Man” and facilitated their decision to cast him as the title character. Many critics along with millions of fans praised Maguire’s performance as the socially inept Peter Parker, catapulting the film to a record-shattering $114 million in its weekend debut.

With a blockbuster under his belt, Maguire wanted another opportunity to exhibit his acting prowess before filming of the sequel to “Spider-Man” began. Along came “Seabiscuit,” the story of the Cinderella horse that rose to become the most popular and winningest horse in the United States during the Great Depression.

Based on the bestselling book by Laura Hillenbrand, “Seabiscuit” reunited Maguire with his “Pleasantville” director Gary Ross and provided him another opportunity to portray an atypical character.

“He was kind of a broken man and kind of desperate,” said Maguire. “He was abandoned with a lot of anger and could be self-destructive.”

Abandoned at a track when he was still a boy, Red Pollard struggled to make his way in 1930s United States, often earning money from amateur boxing matches to supplement his paltry income as a jockey. Pollard’s drive to succeed despite being taller and heavier than his fellow jockeys mirrors Maguire’s life.

“I knew Tobey,” Ross said. “He has lived a difficult life and I knew he had a fire in him – a complexity and an innate toughness.”

Perhaps even more remarkable than Maguire’s acting talent is the extent to which he physically and psychologically prepares for a film. In the case of “Seabiscuit,” the actor, who had bulked up to play Spider-Man, now had to become lean enough to realistically appear as a jockey. Under a supervised 1,650-calories-per-day diet and a rigorous schedule of 16 workouts a week, Maguire was able to lose 23 pounds within a few weeks and acquired the thigh-burning balance necessary for a jockey.

“I did not realize what kind of athletes jockeys are,” Maguire said. “They’re warriors and tremendous athletes.”

For Maguire, the physical preparation for the part helped facilitate the mental preparing as well.

“The preparation for the film excites me, and I dive into it to see something tangible,” adds Maguire. “A lot of the homework that I do is all about learning the psychology of the character. Once you look into the mirror, you need to start to see the character poking through.”

Maguire’s recent success is in deep contrast to his reportedly troubled past. Though it has long been publicized that the actor stopped drinking completely at the age of 19, the August issue of Playboy magazine revealed that Maguire is a member of Alcoholics Anonymous.

However, Maguire remains very candid about his past.

“I don’t think it’s a secret that I’ve been sober since I was 19,” explains Maguire. “It becomes a revelation even though it was out there for years.”

Regardless of his past, Maguire’s dedication and uphill struggle to legitimize his acting abilities to critics and the public are as inspiring as the character he portrays in “Seabiscuit.”