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Sources close to the saga have claimed that producers and film bosses are really keen to keep the 24-year-old on and are making him a big offer.
According to reports, Disney is offering Holland three standalone movies following Spider-Man 3 as well as three further films outside of the Spider-Man saga.
We Got This Covered's source has claimed that people involved with the studio revealed that Disney wants to tell Peter Parker's whole story, from his time at high school right through to his adult life.
But according to Holland, things could have been so very, very different if he hadn't had one phone call... one very drunk phone call with Disney boss Bob Iger.
Despite a lengthy dispute between Disney subsidiary Marvel Studios and Sony Pictures over who would have the ongoing rights to the web-slinging superhero, an accord was eventually reached that allowed Spidey to feature in the Marvel Cinematic Universe as he had been doing previously.
Although it isn't clear whether Holland's drunken emotional input had anything to do with the outcome of the argument, it's certainly possible, right?
Speaking on Wednesday's edition of Jimmy Kimmel Live!, Holland explained how he had asked for the Disney CEO's number in order to thank him for the opportunity to take the role, but ended up on the line with him instead.
Holland told Kimmel: "I got his email, I sent him the email, and he responded very quickly saying, 'I'd love to jump on the phone with you at some point - when are you free?'
"And you don't give Bob Iger a schedule. You're like, 'Whenever, Bob!'"
Now, in this instance, 'whenever' happened to occur while Holland was at a pub quiz and, crucially, three pints deep.
He's not a big lad either, is he?
The actor continued: "I get a phone call from an unknown number, and I have a feeling like, 'I think this is Bob Iger... but I'm drunk.'"
During the call, Holland said that he became somewhat weepy and emotional, not least because he was p***ed, but also because everything 'felt like it was all coming to an end'.
But fortunately for fans, it wasn't, and it looks as though there is plenty more Spidey to come.