Despite earning millions at the global box office and remaining a tentpole brand for Sony Pictures, the Spider-Man franchise took a hit when The Amazing Spider-Man 2 prioritized shared universe building over a self-contained superhero tale. Understandably, The Amazing Spider-Man 2 provided moviegoers with fun summer escapism but, one year after the film left theaters, it's become apparent that the movie not only failed in its goal of launching a standalone shared universe (centered around Peter Parker and the Sinister Six), Marc Webb's Spider-Man sequel actually undercut enthusiasm for a third chapter in the reboot series.
Regardless, Spider-Man brand recognition remained strong, even if faith in Sony Pictures dipped, prompting the studio to coordinate with Disney and bring Peter Parker into the Marvel Cinematic Universe. We've detailed fine points of the deal on multiple occasions and while we know Spider-Man will appear in the upcoming Captain America: Civil War, one questions remains: how much MCU will make it into Sony's solo Wall Crawler films?
Following news that Captain America and Iron Man actors Chris Evans and Robert Downey, Jr. would be returning to Atlanta for MCU duty in the near future, most fans assumed the pair would be filming select Captain America 3 reshoots. However, a recent comment from Spider-Man actor Tom Holland, suggesting the 2017 Spider-Man movie would also film Atlanta, prompted some moviegoers and industry news outlets to make the leap that Steve Rogers and Tony Stark would appear in the Web Slinger's solo outing - specifically that Evans and Downey, Jr. weren't going to Atlanta for Civil War reshoots. Fans theorized that the stars were actually heading to Atlanta for an appearance in the Spider-Man reboot or a Civil War post-credits scene (teasing Peter Parker's next onscreen appearance). After all, The Avengers shot their fan-favorite shawarma post-credits scene in the later stages of post-production, right?
While there's no way to definitively disprove Captain America and Iron Man in Spider-Man speculation at this time, it's important to note that the significantly more likely scenario is that the actors are, as reported before speculation was setoff, headed down to Georgia for Civil War reshoots - an extremely common part of the post-production process.
Nevertheless, it's understandable why fans should want to believe the rumor - since an appearance by Captain America and Iron Man could suggest the upcoming Spider-Man film would actually utilize main MCU characters rather than simply coast on Spider-Man cameos in other Marvel Studios movies. Fans have been concerned that even though the Spider-Man film will be part of Marvel's shared universe, Sony might only allow surface-level connections - so that they could still put the emphasis on developing their own corner of the MCU (one that could still spawn a Sinister Six, Venom, and/or Black Cat spinoff).
Ultimately, the amount of MCU in Spider-Man solo movies going forward will depend on how the agreement between Sony and Marvel can benefit both studios. Sony and Marvel have formed a mutually beneficial partnership but it's also a partnership where both parties reserve a lot of rights (and profits) depending on how the character is used. For that reason, fans shouldn't expect Sony to always roll out the red carpet for MCU characters (or, conversely, expect that Marvel will always be interested in putting their characters into Spider-Man movies). Down the line, both studios might find that the more integration they allow, the better their individual films perform - but we are still in the very early stages of an unprecedented partnership, one that is sure to evolve once the studios see how shared universe partnering actually affects their respective bottom lines.
Captain America and Iron Man in Spider-Man might sound like a no-brainer for viewers but Marvel has to worry about over-saturating the superhero movie market with their characters. Conversely, Sony has to walk a very delicate balance between developing their own sub-brand within the MCU and managing expectations (among other considerations). After all, the MCU isn't free of hurdles still in need of refinement - especially the problem of why Avengers heroes don't team-up to take on villains that threaten Earth in each solo film (and Agents of S.H.I.E.L.D.).
Daredevil and Jessica Jones have managed to eat their cake and have it too, for the time being, acknowledging the MCU with only minor references to The Avengers but after throwing Spider-Man into Civil War Sony will be faced with a tougher challenge - maintain their MCU connections without free-reign over which characters can appear in future Spider-Man films.
Time (and box office returns) will tell where Sony and Marvel agree to draw the line - but, until the studios have a chance to feel-out their partnership, fans should temper expectations. It's an exciting time to be a comic book movie fan but viewers are still at the mercy of studios who are making decisions based on maximizing their profits - not necessarily catering to what die-hard fans might hope to see.
So, to answer the question at hand: will Captain America and Iron Man appear in the Spider-Man solo movie? Maybe but only if both studios decide it would be mutually beneficial.
Captain America: Civil War will release on May 6, 2016, followed by Doctor Strange– November 4, 2016; Guardians of the Galaxy 2 – May 5, 2017; Spider-Man – July 28, 2017; Thor: Ragnarok – November 3, 2017; Black Panther – February 16, 2018; The Avengers: Infinity War Part 1 – May 4, 2018; Ant-Man and the Wasp – July 6, 2018;Captain Marvel – March 8, 2019; The Avengers: Infinity War Part 2 – May 3, 2019;Inhumans – July 12, 2019; and as-yet untitled Marvel movies on May 1, July 10 and November 6, 2020.