Star Wars: 9 Burning Questions About Lando's Return In Episode IX
9. Where Has He Been?
The last time audiences saw Billy Dee Williams as Lando Calrissian was all the way back in 1983, in Return of the Jedi. Not only is that over thirty years of real-time, it's also over thirty years of time in the Star Wars Universe. Since the last time we saw Lando, the Empire has been snuffed out, the Galactic Republic has been reformed and subsequently destroyed, and the First Order has taken over.
That's a lot of stuff for Lando to have simply been sitting out.
There hasn't even really been an explanation in the expanded materials as-of-yet, with the most applicable story being Daniel José Older's novel, Last Shot, which has a section set a few years after the end of Return of the Jedi and two years after the fabled Battle of Jakku. And although his connections to Cloud City are still made clear here, no explanation is given as to where he might have gone in the decades since.
Whatever the explanation is, it must be something good. Because while it is important to remember that the events of both Force Awakens and Last Jedi unfold over a reasonably short period of time, the First Order destroyed several planets and all but obliterated the Resistance. Hell, no one answered Leia's final distress signals on Crait at the end of Last Jedi.
Lando, sounds like you've got some 'splainin' to do.