Fifteen years ago last May, Sam Raimi's Spider-Man debuted to an astounding $100 million+ in its first three days of release — until then, the White Whale of opening weekends. The franchise, which is one of the most successful in history, is due for its second reboot with this week's Spider-Man: Homecoming. But even though Marvel Comics’ web-slinger has now become a valued, signature property for Sony Pictures, he spent more than a decade lingering in development hell before his first movie hit theaters in 2002.

Bear in mind that, until very recently, Marvel had never enjoyed a successful big-screen adaptation. Not one. This might seem hard to believe in today's post-Iron Man age, but back then their cinematic prospects were one long, uninterrupted joke, with mega-flops like 1986's Howard the Duck and also-rans like 1990's The Punisher and Captain America (not to mention the 1994’s never-released Fantastic Four) serving as periodic punch-lines. But the timing couldn't have been better for Spidey.

 Five years earlier, crosstown rival DC Comics’ Batman series had famously flamed out, and the perpetually "upcoming" Superman reboot had spent nearly as long in development hell as the Spider-Man project had. Things finally turned around for Marvel in 1998, thanks to a little known character from the publisher's far fringes. No one thought Blade would do much of anything when it opened in late August, but lo and behold, the action-horror pic starring Wesley Snipes as a vampire hunter (created by Marv Wolfman and Gene Colan) racked up $70 million domestically, proving that, when done well, even one of Marvel's lesser lights could find an audience. Imagine what could happen with one of its marquee characters!

After sorting through a deep pool of directing candidates, the gig went to Sam Raimi, a longtime Spider-Man fan who previously tried his hand at the superhero genre with 1991's Darkman, and who felt — rightfully so — that the appeal of Spider-Man over the years wasn't just his regular face-offs with diabolical super-villain types. Rather, it was Peter Parker’s grief over the loss of his beloved Uncle Ben, struggles to pay the rent and keep his grades up, and efforts to make sense of his topsy-turvy love life.

The next step was casting, and here again Sony had their pick of talent. But it was Tobey Maguire, who had built a solid rep in prestige films such as 1997's The Ice Storm and 1999's The Cider House Rules, who got the nod — after filming a shirtless stunt sequence. From there, Kirsten Dunst was tapped to play love interest Mary Jane Watson, Willem Dafoe was cast as Norman Osborn (Spidey’s archenemy the Green Goblin), and James Franco (who missed out on the lead) snared the second-prize role of Peter Parker's best friend and romantic rival Harry Osborn.

Watching Spider-Man today, it's easy to see why it worked as well as it did, while also fully acknowledging those parts of the machinery that have gathered some rust in the interim. Much of the credit for what works has to go to Raimi, who threads the needle between the mainstream, "franchisey" flick the studio required, while also finding enough quirky "little" moments to make the big moments more than just noise. Maguire and Raimi find an easy rhythm for Peter Parker, ensuring that you can't help but like him. Of course, it helps that the character of Spider-Man is himself so iconic and relatable that the filmmakers don't have to do much.

With a $115 million opening weekend in May of 2002, a proposed sequel immediately went from hypothetical to inevitable. Director Sam Raimi shifted gears immediately after the first film's release to begin prepping the follow-up, which was released just two years later in the summer of 2004. And he didn't miss a step. Spider-Man 2 displays the kind of poise and confidence that can only happen when you’ve created critical smash that is also one of the most successful movies of all time.

With episodic franchise series such as this, the questions surrounding any sequel are less about what our hero will be up to than which bad guy he'll face off against. Raimi & co. settled on Otto Octavius/Doctor Octopus, one of the most prominent and pre-eminent rogues in the not-inconsiderable gallery of Spider-baddies. For the director, these films were about Peter Parker first, and the villains needed to tie in with the guy behind the mask. To this end, he made Octavius (Alfred Molina) a longtime idol of Peter's whose journey to the dark side isn't intentional, and from which he must be redeemed ("Intelligence is not a privilege, it's a gift, to be used for the good of mankind," he tells Peter at one point).

What makes Spider-Man 2 work, then, is that the filmmakers do right by the audience, advancing the plot enough that by story's end it feels like we've gotten somewhere. Like the first film, this entry was greeted with near-unanimous critical acclaim upon its Independence Day release, with the consensus being that it improved on its predecessor by striking the right balance between small, human moments and big blockbuster stuff. While no records fell, Spider-Man 2 still made almost $800 million worldwide.

With a second successful entry, it seemed that the brain trust behind the Spider-Man movie series had figured out the magic formula and were strapping in for a very long, relaxing ride. Unfortunately, 2007's Spider-Man 3 is the unquestionable nadir of Raimi’s franchise: an overstuffed spectacle where the fingerprints of studio interference are a little too obvious, and a forced, altogether unsatisfying conclusion to a series that had hit some pretty satisfying creative highs during its short lifespan. However, before we begin launching the brickbats (and there are plenty), it's helpful to bear one small thing in mind: Spider-Man was never meant to be a trilogy. 

Sure, nowadays everything gets forced into the three-and-done model, but more and more the deployment of "trilogy" has become a lazy crutch to add portent where there isn't any. The necessary component is that while each of the works can stand separately from each other, when taken as a whole, there's a dramatic build-up across all three that comes to a satisfying emotional pay-off. Closure. By its very nature, the Spider-Man story doesn't lend itself to such a format because it has no ending. Thus, while certain long-running threads are wrapped up (specifically the Harry Osborn arc), others are left in place (Peter and Mary Jane's romantic tribulations), to be picked up when the inevitable next entry happened.

Of course, that hypothetical next entry never materialized, and so, ten years later, we're forced to look at a Spider-Man 3 that's rendered even weaker now than it was at the time of its release. It's now unsatisfying both on its own and, as the closing act of an ex-post-facto "trilogy", with all the concomitant expectations that term implies. Spider-Man 3 is soap operatic in the very worst way, propelled by a frustrating chain of coincidences.

For example, it just so happens that the man who killed Peter’s Uncle Ben (Thomas Haden Church’s Flint Marko) has gotten superpowers and become the villainous Sandman.And then there’s Venom. One of the most prominent Spidey villains in the late '80s and into the '90s, Venom’s crazy popularity even led to him headlining his own line of comic books for a little while as a sort of pseudo hero. But having grown up primarily with the original set of '60s-era Spider-villains, Raimi had no desire to dip his feet into '90s excess. Nonetheless, producer Avi Arad strongly suggested that he find a way to include the villain in the mix. Thus, as played by Topher Grace, Venom’s arbitrary inclusion (he's never once even referred to by that name) and sudden disposition smacks of Raimi telling his studio, "Fine! You want Venom? Here! Oh, he's dead."

It's frustrating how Thomas Haden Church is forced, thanks to all the other plotlines requiring attention, to sit out most of the film. Haden Church is really good here — at least as good as Molina's Doc Ock — and with a little more breathing room, Raimi could potentially have spun this into a far richer cinematic experience that still did right by the audience. At the time of its opening, Spider-Man 3 set a new opening record with a $151 million weekend, proving how much goodwill the franchise had generated with its first two installments.

However, the drop-off from week one to week two was more severe, proving that this latest entry had left a bad taste with audiences. Although its global haul of nearly $900 million was the best of the series, its domestic total of $336 million was the lowest. But while Spider-Man 3 was indeed hobbled by its kitchen-sink storyline, it still put enough butts in seats to become the highest grossing entry in the series globally. Thus, Raimi and Maguire were webbed back in for a fourth go-round.

But when Raimi ran into story problems on the proposed Spider-Man 4 that threatened to push back his schedule, Sony chose to cut bait and start over. The whys-and-wherefores of this decision come down to the rights arrangement between Marvel and Sony for Spider-Man, which specifies that any lull in the franchise’s assembly line likely means the character and his ancillary properties snap back to Marvel.

And for as much as Disney would no doubt love that, Sony really wouldn't. And thus, once Raimi threw his hands in the air and told Sony he couldn't make their 2011 goal, they quickly went into Plan B mode, pulling out a Frankensteined-together "back to basics" script by James Vanderbilt, Steve Kloves, and Alvin Sargent that was sitting in a glass box marked "Break in Case of Creative Inertia," and hiring director Marc Webb, a relative newbie to franchise filmmaking, to put it all together. And just like that, the decade-old series was rebooted with 2012’s The Amazing Spider-Man.

But while many of the story beats were, out of necessity, the same, there was enough difference to keep the reboot from being entirely redundant or perfunctory. As embodied by Brit actor Andrew Garfield, the 2012-model Peter Parker wasn’t so much a nerd as he was an outcast loner in the James Dean mold. Meanwhile, Webb put the skills he had demonstrated in 2009's charming (500) Days of Summer to good use by using Peter and love interest Gwen Stacy (Emma Stone) to paint a believable portrait of blossoming young love in the face of threats from designated baddie the Lizard, a.k.a. Dr. Curt Conners (Rhys Ifans).

The Amazing Spider-Man made $750+ million against a $230 mil budget. While this was the lowest-grossing entry of the franchise so far, it was still a substantial-enough haul to show there was still considerable hunger for Spidey’s cinematic adventures. As such, Sony’s gamble by insta-rebooting the series wasn’t a total disaster, and since by this point they were already committed to the new direction, production quickly got underway on Webb’s The Amazing Spider-Man 2, which would arrive in theaters two years hence again starring Garfield and Stone.

But if these movies live and die by their villains, then The Amazing Spider-Man 2’s Electro (Jamie Foxx) is a warmed-over version of Jim Carrey's Edward Nygma in 1995's Batman Forever. He goes from fawning Spider-Man fanboy to furious Spider-Man foe while pretty much hopscotching right over the beats to get us from point A to point B. Batman Forever did it better (which is just a weird, weird sentence to type).

Because of Sony's ambitious (read: risky) plans to spin-off (read: strip-mine) the Spider-Man rights for all they're worth, The Amazing Spider-Man 2 was tasked not only with furthering its own internal storyline, but also with laying the foundation for several other potential franchises. As a result, it had a few too many balls in the air, and a few too many plot threads randomly started or abruptly ended, feeling at times like two separate movies awkwardly scotch-taped together, neither of which proved particularly compelling to audiences.

While studio execs boldly predicted that Amazing 2 would easily clear a billion dollars at the global till, its $709 million worldwide total not only fell substantially shy of that high bar, it was also the lowest of any entry in the series. This, in turn, prompted the studio to quickly reverse course on their ambitious sequel and spin-off plans while reassessing their prospects. While they could well have continued with the Webb-Garfield series and hoped for the best, they instead decided to partner with Marvel Studios for an unprecedented deal that would see both companies co-producing the Webhead’s next installment.

This time around, Spidey would arrive with the implied credibilty that comes with being ensconsed within Marvel’s hugely-successful cinematic universe. Fresh face Tom Holland would debut in the role via an extended cameo in 2016’s Captain America: Civil War, then seamlessly segue into his own eponymous feature film, Spider-Man: Homecoming itself bolstered by the presence of Robert Downey Jr. as Tony Stark/Iron Man.

As directed by Cop Car's Jon Watts, Homecoming) is pretty standard-issue stuff when it comes to this character’s conflicts, weaving together Peter Parker's superhero stress (minus the need to retell his origins yet again, thank goodness), the usual high school angst, and the designated baddie's Big Evil Plan (those duties this time are filled by Michael Keaton, glowering with villainous glee as working class inventor-turned-megalomaniac the Vulture).

But none of that should be interpreted as a debit against the film. Rather, the description above sums up Spider-Man’s singular, multi-generational popularity that abides through multiple reinterpretations over the years, whether via comics or cartoons or movies. When you think about it, Homecoming’s very existence is a testament to how valuable a property Spider-Man is for all involved. Indeed, it tells you how strong of a hand Marvel had that they were doing just fine even without the single most lucrative superhero on Earth as part of their lineup.

Not very many franchises would get as many at-bats after three cold resets inside of fifteen years, much less prompt two studios to declare an armistice for the collective good of their shared property. But then not many IPs outside of Star Wars command the same global loyalty or boast as much merchandising clout. Ultimately, whether it’s Tobey Maguire or Andrew Garfield or Tom Holland angst-ing away behind the mask, the resilience of the brand jillustrates how the Spider-Man myth is more powerful than any of its individual tellings, and why he will likely continue to spin his webs onscreen for decades to come.