Matt Damon has collected legendary roles the way Odysseus collected impossible quests. He wrote himself into Academy Award history with Good Will Hunting, transformed Jason Bourne into modern action's gold standard, and made a stranded astronaut in The Martian irresistibly charming. Now, Homer has handed him Odysseus, because apparently ordinary legends were no longer enough.

Yet even an actor playing Odysseus regrets that age, unlike any mythical obstacle, kept him from ever becoming the friendly neighborhood superhero, Spider-Man.

Matt Damon may be charting Odysseus' legendary voyage in Christopher Nolan's The Odyssey, but Complex's GOAT Talk steered him toward a different hero. Asked to crown the greatest superhero of all time, Damon sat beside co-star Tom Holland, who plays his son in the film, and playfully stretched out his answer, teasing the Marvel star before finally revealing his pick as well as his regret surrounding the superhero Spider-Man.

"You know, I just missed it," Damon said while admitting that Spider-Man would be the best superhero for him. He also revealed that he regretted not being able to play him because of his age. At that time, Tobey Maguire, who was 4 years younger than him, was playing Spider-Man. Because of that, Matt Damon, who was 32 years old at the time, believed he had already become too old to chase the role professionally, no matter his love for Spider-Man.

Matt Damon revealed in Complex's GOAT Talk that Spider-Man was, in fact, his childhood favorite because he used to dress up as the web-slinger. The heartfelt moment ended with Holland stealing the last laugh. After Damon praised the actors who wore the suit, Holland quipped that the casting lineup "went to s*** again," gleefully making himself the punchline.

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Matt Damon may have missed the web-shooters, but he hardly missed his date with Hollywood history.

When Sam Raimi's Spider-Man turned Tobey Maguire into an overnight superhero phenomenon in 2002, Matt Damon was busy engineering a reinvention of his own. The Bourne Identity arrived barely a month later and transformed Damon into an action powerhouse, while Gerry revealed his appetite for fearless arthouse storytelling. Even Spirit: Stallion of the Cimarron showcased another side of his versatility through narration rather than spectacle.

Years later, that willingness to chase unlikely paths carried Damon back to Christopher Nolan, whom he has described as a unique filmmaker to work with, for The Odyssey. Trading Jason Bourne for Odysseus proved that some careers only grow more adventurous with time. Ironically, the one role Damon still cannot stop wondering about is the friendly neighborhood superhero who got away.

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Do you think Matt Damon would have made a good Spider-Man? Let us know in the comments!