After Disney bought Lucasfilm from founder George Lucas for an amazing $4 billion, the studio was quick to announce the news that starting with 2015's long-awaited Episode VII AKA The Force Awakens that Star Wars fans would be getting a Star Wars movie every year for the foreseeable future. To achieve this Lucasfilm announced that each year the movies would see-saw between episodic installments and non-episodic spin-offs originally called Anthology movies, but now called "Star Wars stories". It didn't take too long for Lucasfilm president Kathleen Kennedy to confirm the production companies schedule for the next five movies to include next months Rogue One and 2018's Han Solo movie. Originally planned to follow 2019's Episode IX (to be directed by Jurassic World's Colin Trevorrow) was a Boba Fett movie directed by Josh Trank but after the major disappointment that was Fant4stic Lucasfilm was quick to cut ties with the Chronicle director, leaving the third "Star Wars Story", expected to be released in 2020 as a blank slate.
Recently Collider had a video interview (included above) with the Star Wars prequel trilogy star Ewan McGregor in which the actor confirmed his brief vocal appearance in The Force Awakens, the Scottish actor also related his interest in returning on-screen as the character of Obi-Wan Kenobi before tip-toeing around the question of whether or not he had met with Lucasfilm to discuss that very possibility. This has caused a wealth of speculation that the 2020 "Star Wars Story" movie will be an Obi-Wan movie set, like next month's Rogue One between Episodes III and IV of the saga, possibly exploring the characters self-induced exile on Tatooine or possibly exploring the characters ties into the rebel alliance and why Princess Leia Organa called for his aide.
While Lucasfilm has yet to deny that an Obi-Wan movie is in development Entertainment Weekly's Anthony Breznican inferred recently while appearing on the Rebel Force Radio podcast that the reason why Lucasfilm has not pressed ahead with an Obi-Wan solo movie is because they have allegedly not finished with his character in the new sequel trilogy. Considering the characters brief sound bite in The Force Awakens and the characters known ties to Luke Skywalker it could prove to be that this is the case and will likely be confirmed if the character makes some sort of appearance in next year's Episode VIII, which is currently in production and is being directed by Rian Johnson. If indeed Kenobi makes an appearance in Episode VIII and it is welcomed by fans and critics an announcement by Kathleen Kennedy would likely so follow confirming that an Obi-Wan movie is planned for 2020.
Post-2020, however, the known future of the Star Wars movies is less clear. Fans and critics believe that Lucasfilm may explore a fourth and possibly final trilogy in the Star Wars saga either set a generation after the current sequel trilogy or possibly continuing the story arc of the characters of Rey, Kylo, Poe, and Finn. Another possibility could be another prequel trilogy set somewhere in the saga's past, maybe exploring the old republic or the formation of the Jedi and/or the Sith orders. Whether or not Lucasfilm will continue to develop the stand-alone Star Wars Story movies will depend upon the commercial, critical and fan reception of Rogue One and 2018's Han Solo spin-off.
Beyond an endless barrage of episodic and spin-off movies from now until the end of time, it may be interesting to see Disney and Lucasfilm follow the example of Marvel Studios with one or more small screen properties stemming from the Star Wars saga. Fans will argue this is already the case with the Clone Wars and Rebels animated series. Yet most casual Star Wars fans and Star Wars enthusiasts would likely prefer one or more live action serials exploring either the story of a popular character or exploring one of the saga's many key elements - more specifically, Disney and Lucasfilm could develop a live action Rogue Squadron TV show, which would attract fans of the saga and of favored 80's sci-fi properties such as Battlestar Galactica and Buck Rogers.