Although his dashing turn as a web-slinging superhero in the Spider-Man trilogy turned him into an international sensation, this thoughtful leading man seduced critics long before he began making teenagers swoon. As a child actor in the early '90s he made guest appearances on sitcoms (Roseanne) and dramas (Jake and the Fat Man). In fact, he met his best friend/future fellow superstar Leonardo DiCaprio at an audition for the TV adaptation of the movie Parenthood. In 1992, Maguire snagged his first series regular role, as the nerdy title character in Great Scott!, but after that show went bust he turned his attention to the big screen, making his film debut opposite DiCaprio in This Boy's Life. Although his buddy's career immediately took off, Maguire spent a few more years playing the stereotypical cute but goofy kid in grade-Z dreck like Revenge of the Red Baron and Joyride. But in 1997 he burst onto the indie radar as the pensive suburban narrator of the art-house hit The Ice Storm. Suddenly Maguire was the go-to awkward but appealing adolescent, playing a series of similar types in high-minded pictures (Pleasantville, The Cider House Rules, Wonder Boys). Peter Parker, the civilian side of Spider-Man, was very much in keeping with those roles, a hardworking high-school geek with an unrequited crush on the girl next door. But to play his super alter ego, the young star had to buff up his body and beef up his sex appeal, with impressive results. Although he helped turn Spider-Man into one of the biggest hits in cinema history, Maguire almost didn't return for the subsequent sequels. Officially a back injury sustained while playing a jockey in Sea Biscuit was what caused Maguire's fitness for the project to be called into question, but rumors circulated that his demands for more money were what really prompted the studio to threaten to replace him with Jake Gyllenhaal. Whatever the truth, fans were glad to see Maguire back in the skin-tight, red-and-blue suit, and his palpable pathos as Parker helped separate the films from other comic-book flicks.