Now, he's swung into a lucrative multiverse of crossover possibilities on the big screen, owing to a Hollywood licensing deal that ties the wall-crawler's adventures to Marvel Studios' Avengers.
While teaming up the $4-billion US Spider-Man franchise with Spidey's amazing new friends is a coup for comics fans, the pact between Sony and Disney's Marvel Studios also illustrates the messy web of intellectual properties that lawyers must untangle to bring superheroes to the big screen.
Speaking as a copyright attorney and "long-time comics nerd," Peter Henein said the deal presents one resolution to a "fascinating" legal quagmire.
"You have to imagine how much had to be agreed upon just to have Spider-Man show up to say 'hi' to Captain America on film," he said.
"Any lawyer who's going to be working on those kinds of extensive deals would have their work cut out for them."
The origin of the legal complexities behind comics-on-film goes back years ago to the piecemeal sell-off of superhero licensing rights to studios.
Suddenly, characters who casually visited into each other's titles in comic-book pages couldn't make the same leaps on film because they were bound by a patchwork of licensing agreements.
The properties for the cinematic rights were, in part, parcelled out like this:- Twentieth Century Fox: X-Men characters, the Fantastic Four and Silver Surfer.
- Sony Pictures Entertainment: Spider-Man and ancillary characters.
- Marvel Studios/Disney: The Avengers (including Iron Man, Captain America, Hulk, Thor, Hawkeye and Black Widow) and the Guardians of the Galaxy.
- Warner Bros.: Batman, Superman and the Green Lantern.
Without having seen the exact terms of the Sony-Marvel deal, Henein said it's likely Sony would "sub-license" the Spider-Man character for a Marvel Studios film slated for 2017, while retaining creative control.
"For example, if the screenwriters of Captain America 3 decided it would be an interesting twist to kill off Spider-Man in the first 15 minutes, Sony would presumably be disappointed because it limits their ability to use that character in the future," Henein said.
Such a scenario would be highly unlikely, of course.
For Henein, the prospect of a beloved Marvel hero like Spider-Man finally being "unchained" by Sony to mingle with the Avengers, who have helped Marvel reap over $7 billion at the global box office, "is a very exciting development."
Doubly so for Marvel Studios, and for Sony in particular.
The company was struggling with disappointing box-office returns from last summer's The Amazing Spider-Man 2, starring Andrew Garfield.
Having Sony reach out to Marvel for a lifeline on the flagging franchise seemed a sensible move to Chris Bird, a Toronto lawyer who also writes the web comic Al'Rashad: City of Myths.
"This is a big deal for fans because Sony has not been the greatest steward of Spider-Man," Bird said.
It also serves as a reminder, he said, that gone are the "innocent days" when comic characters from Marvel or its rival publisher DC freely intermingled across titles and even companies.
Superhero comics are now considered to be multibillion-dollar properties, with a Comics Alliance infographic mapping out at least 36 planned comics-based films for the next five years and beyond.
Reboot before rights expire
Such an abundance of titles would seem to be overkill for the studios, but a rights incentive obligates them to keep using characters within a set amount of time, lest the licensing deals expire.
The 2012 Spider-Man reboot is an oft-cited example.
Fans like Jules Greco speculated that the production of The Amazing Spider-Man, coming just five years after the Sam Raimi-directed Spider-Man 3, may have been driven by Sony's unwillingness to relinquish the property, which would have reverted back to Marvel if no Sony followup was made.
"A lot of it is a total money grab," said Greco, a sales associate at Toronto's Silver Snail comics. "Companies try to hold onto their properties by making new things."
Twentieth Century Fox, which developed 2003's Daredevil starring Ben Affleck, never produced a sequel and lost the cinematic rights to the blind vigilante hero and associated characters on Oct. 10, 2012. Marvel Studios reclaimed the character for the cineplex, and a Netflix original series titled Marvel's Daredevil is set to premiere in April.
In the meantime, Greco said there are rumours among comic fans that the publisher Marvel Comics could be quietly shelving characters whose cinematic rights are owned by rival firms to Marvel Studios.
The X-Men character Wolverine was killed off last October in the comics, and the long-running Fantastic Four saga was also discontinued the same month. Movie versions of characters from both series are owned by Twentieth Century Fox.
Bird has discussed the same theories with some comic creators. "But I want to stress we're deeply into conspiracy theory territory now," he said.
One way or another, Bird said the potential for a thawing of licensing deals, as shown by the Spider-Man and Avengers crossover, should make geeks happy.
"The general perception in fan circles is that the movies Marvel makes themselves are the best Marvel movies overall," he said. "And if Marvel gets to make a Spider-Man movie, well, to fans, that means you get to see Spider-Man the way he should be."