Hollywood history is a series of paths that were taken, movies created, and destinies forged by the results. Which is why the paths NOT taken are always so fascinating to think about. What if the Eric Stoltz version of Back to the Future got made? Or if The Lord of the Rings had gone ahead with Stuart Townsend instead of Viggo Mortensen. Or Natalie Portman had played the Sandra Bullock role in Gravity.

One particular what-if scenario that came very close to happening concerns Jake Gyllenhaal, Tobey Maguire, and the lead role in the biggest sequel of all time. After the first Spider-Man movie opened HUGE in the summer of 2002, blockbuster filmmaking — and superhero filmmaking in particular — was shot into another sphere. Suddenly, the biggest movie star in the world was the rather unlikely Tobey Maguire, who up until this point had been alternating his career between a series of rather oddball young men in movies like Wonder Boys and Fear and Loathing in Las Vegas and comparatively bland leads in movies like The Cider House Rules, where the supporting characters really get to shine.

Obviously there was going to be a Spider-Man 2, with Raimi back behind the camera and the central trio of Maguire, Kirsten Dunst, and James Franco set to return. But in between films, Maguire made a little movie called Seabiscuit, another one of those movies where he was the lead but everybody else (including the horse) was more memorable. The film was a huge hit and an eventual Best Picture nominee, but Maguire suffered a back injury while filming, and it was beginning to seem like he wasn’t going to be healed in time for Spider-Man 2 to start filming. At which point Sony got nervous and began looking around for contingency plans.

They looked to Jake Gyllenhaal.

Gyllenhaal’s career had been an odd mirror to Marguire, except much, much heaver on the oddball creepos. In both The Good Girl and Lovely & Amazing, he played a cute younger man who gets involved with a spiralling woman (Jennifer Aniston and Catherine Keener, respectively). In Donnie Darko he played a doomed and disturbed young man haunted by a giant rabbit and getting messages about the end of the world. In Bubble Boy, he played a bubble boy. You could see the studio calculus that deduced that a Tobey Maguire could be easily replaced with a Jake Gyllenhaal. After several weeks of speculation, Maguire was indeed able to return to action, and the Gyllenhaal-as-Spider-Man thing became another great “what if,” one that got more and more tantalizing as the years went on and Gyllenhaal would break out huge with movies like Brokeback Mountain, Jarhead, and Zodiac.

But what if Gyllenhaal had actually stepped in to play Peter Parker in Spider-Man 2 (and presumably also the third, crappy, very dance-centric Spider-Man 3), putting him in a fraternity with the likes of Christian Bale, Hugh Jackman, Ryan Reynolds, Robert Downey Jr., and any number of Chrisses — essentially the entirety of American male leading men. These days, it’s almost impossible to be a leading man in Hollywood and not have some kind of superhero or at least action-hero franchise under your belt. Gyllenhaal just … never has. Not for lack of trying, I suppose, since he did make Prince of Persia: The Sands of Time, but I suppose we can all be thankful that movie bombed.

In many ways, it was the bounce-back from Prince of Persia that had led Gyllenhaal to this truly most excellent and bizarre phase of his career. He’s become one of our more unpredictable actors, bouncing from gritty police drama (End of Watch) to jacked-up boxer (Southpaw) to impish science-adventurer (Okja), to pure trash (Nocturnal Animals) to pure inspiration (Stronger). Even when he takes seemingly staid roles in a detective noir (Prisoners) or a western (The Sisters Brothers), his characters tend to be deep wells of strangeness. Even the unlikely reunion with the Spider-Man franchise this summer will see him playing Quentin Beck/Mysterio, a deeply strange and self-referential character within that milieu.

Nightcrawler, the film Gyllenhaal made with director Dan Gilroy in 2014, is a great example of a movie that could have been made far more simply (the story of a crime-scene photographer who gets in over his head) but became an attention-grabber because of Gyllenhaal’s singular, often unhinged performance. We’re all pretty much looking forward to something similar emerging in Gilroy’s Velvet Buzzsaw, which drops on Netflix this weekend.

Is Jake Gyllenhaal this daring of an actor if he’s gut a cushy action franchise to fall back on? It’san intriguing wormhole-universe to consider. I say he’s not. I say thank God Tobey Maguire was able to get back to slinging webs back in 2004. We’re all the richer for it, in one way or another.