Lando Calrissian (Credit: Lucasfilm)
Lando ‘I Didn’t Mean to’ Calrissian
He hit on Princess Leia from the start and only wasted like .2 seconds before he betrayed them.
Though he defected by the end of The Empire Strikes Back and decided to join the Rebellion, Lando Calrissian already made a very crucial mistake that led to more than a few problematic moments in the movies.
So, our heroes get to Cloud City and Lando hands them over to Darth Vader because of his own fear and selfish reasons. Afterward, Han is tortured (“They didn’t even ask me any questions.”) and frozen in Carbonite, C-3PO is dismantled and Leia ends up enslaved at Jabba’s Palace. I know she was captured way after the fact, but she would not have been in Carkoon if Han Solo wasn’t taken in the first place.
The best thing Lando did in The Empire Strikes Back was set up the scene where Princess Leia says ‘I love you’ to Han Solo. Obviously, he made up for it in the next movie when he blew up the second Death Star, but man, he needed to get punched in the face a couple more times.
However, I am curious to see how Donald Glover plays the character in the future Han Solo standalone.