In 2002, Maguire shot to superstardom as the web-slinging superhero Spider-Man in Sam Raimi's Spider-Man, based on the popular Marvel comic book series. He reprised the part in Spider-Man 2 (2004) and Spider-Man 3 (2007).

Maguire's performance as Spider-Man initially earned him some glowing reviews. For instance, Mark Caro of the Chicago Tribune felt that "with his big, round, soulful eyes, Maguire always has been able to convey a sense of wonder, and his instinct for understatement also serves him well here". Towards the third part of the franchise the actor experienced some backlash in the media. "For his part Mr. Maguire needs to stop relying on those great big peepers of his: simply widening your eyes to attract attention does not cut it when you’re over 30", remarked Manohla Dargis of the New York Times in her review of Spider-Man-3.

Though Maguire has not yet signed on for another sequel, the actor has denied reports that he will not return, stating, "I feel like