9. Lobot
What you see in the films: A dedicated assistant to Lando Calrissian, Lobot's head gear seems to be connected to the technological heartbeat of Bespin. Think Bluetooth headset on steroids.
The expanded backstory: Lobot's headpiece is actually permanently attached to his skull, and was done so as a punishment when he was a young boy. He was hooked up to the central Cloud City computer and sentenced to perform menial tasks as part of his community service. He ends up serving multiple city administrations, including Lando's. In the Playstation game Star Wars Demolition, he infiltrates Jabba's palace on a revenge mission, ultimately being forced to participate as a contestant in Jabba's demolition derby tournament.