The lack of Billy Dee Williams' Lando Calrissian in the new Star Wars movies is a surprising one - especially as Williams has made it clear he's fine returning to the character, as he recently has with Rebels. But according to Rian Johnson, Lando almost made it into The Last Jedi... before he realised that the role he planned didn't quite fit.
Speaking to The Playlist about the classic character's absence, Johnson admitted he did briefly consider including Lando. It would have been during Finn and Rose's arc of the story, where the two are tasked with a secret mission from Poe to find a master codebreaker on the casino world of Canto Bight that could shut down the First Order's advanced tracking systems - a role that would, in the final film, be performed by a new character, Benicio Del Toro's morally ambiguous hacker, DJ. But the problem is, Finn and Rose's search ends in tragedy - DJ sells them out to the First Order, and not only do they fail to disable the tracker, DJ gives the First Order codes to track the Resistance's sensor-cloaked evacuation ships, costing the lives of untold Resistance members as they flee to Crait.
The whole point of DJ's betrayal is wrapped in the larger message the Canto Bight sequence of The Last Jedi is meant to hammer home: there's a whole galaxy of people out there who are invested in the cyclical rise and fall of Republics and Empires because it's good for filling their pockets rather than it being good for the wider galaxy. Not everyone has a heart of gold or is willing to do the right thing for other people. That message is important to The Last Jedi's wider themes about hubris and failure, but Johnson quickly realised that such a message couldn't be taught coming from a character like Lando:
I don't think you would ever buy that Lando would just completely betray the characters like that and have that level of moral ambiguity. Cause we love Lando and you'd come into it with that [expectation]. And also, DJ, the character that they met, for the purposes of Finn's character, had to be a morally ambiguous character that you're not sure about, that you're guessing about, and we already know that we love the character of Lando so it just wouldn't have played in that part story wise.
Sure, it's the role Lando initially plays in Empire Strikes Back - don't forget, his first instinct is to sell Han and Leia out to Vader in an attempt to keep Cloud City's independence and businesses out of Imperial hands - but it wouldn't have made sense for the character that Lando became by the time of Return of the Jedi, someone willing to be invested enough in the fight that he's a general leading the charge at the battle over Endor. Seeing him return only to callously sell out the Resistance to line his own coffers would have been horrifying.
While it means no Lando just yet, in this instance, it was for the best that this role was filled by a new character, instead of a familiar face that we know and love.