Per a report about the MCU’s new entry in “The Guinness Book of World Records”:
Since the two actors [Tobey Maguire and Willem Dafoe] reprised their roles in what is technically a continuation of their original series, they now have the longest careers as live-action Marvel characters.
Maguire and Dafoe made their debuts as Peter Parker and Norman Osborn Sam Raimi’s Spider-Man, which hit theaters in 2002. They returned to play those characters 19 years and 225 days after that first movie, breaking the previous record set by Hugh Jackman, whose career as Wolverine spanned the 16 years and 232 days between X-Men and Logan.
It is worth noting that Mandalorian creator Jon Favreau’s Happy Hogan is the longest-tenured character native to the MCU at this time. Hogan, the chauffeur and confidante of Iron Man/Tony Stark (Robert Downey, Jr.), first appeared in the MCU’s debut movie, Iron Man (2008).
At this time, it remains unclear if Sony Pictures and Marvel Studios will continue their relationship. Spider-Man producer Amy Pascal has already teased a fourth Spider-Man collaboration — and an entire second trilogy, in fact — between the two studios, but Sony Pictures was quick to note that this has not yet been officially confirmed.
Joining Spider-Man: Homecoming (2017) and Spider-Man: Far From Home (2019), the official description of Spider-Man: No Way Home reads:
For the first time in the cinematic history of Spider-Man, our friendly neighborhood hero is unmasked and no longer able to separate his normal life from the high-stakes of being a Super Hero. When he asks for help from Doctor Strange the stakes become even more dangerous, forcing him to discover what it truly means to be Spider-Man.