Lando Calrissian was a professional gambler, entrepreneur, smuggler and long-time associate of Han Solo. A Human male from Socorro, Calrissian became Baron Administrator of Cloud City for a time before the Imperial takeover during the Galactic Civil War. He subsequently joined the Rebellion, and led the dangerous mission to enter the second Death Star's core and destroy its reactor.
Already a professional gambler, Calrissian won a battered YT-1300 freighter called the Millennium Falcon in a high stakes game of sabacc. Calrissian had no piloting experience, and so sought out a tutor by the name of Han Solo.
Hoping his run of good luck would last, he entered the Cloud City Sabacc Tournament, but wound up in second place, and gave his old friend Han Solo the choice of any ship on his used starship lot. Han, unexpectedly to Lando, chose the Millennium Falcon, the ugliest but most efficient ship in the lot.
Some time later, Lando assisted Han in an attack on the Hutt spice and slavery operations on Ylesia, which Han was involved in due to being in love with Rebel agent Bria Tharen, the mastermind of the operation. Han recruited several smugglers for the strike, including Lando. In the end, they were successful, but Bria decided to keep the spoils for the Rebellion, leaving Han with nothing to pay Lando and the smugglers, and creating a large rift between Solo and Calrissian.
While on Cloud City, Lando played a game of sabacc against the Baron Administrator Dominic Raynor. An anonymous benefactor advanced Calrissian five million credits. He bet all 5 million against Raynor's administratorship, and won the whole game, becoming the new Baron Administrator of Cloud City. The benefactor turned out to be Cloud City's cyborg liaison, Lobot, and the pooled funds of thousands of Ugnaught workers who wanted to ensure Raynor's departure.
As a key source of Tibanna gas, Cloud City was a lucrative target for Imperial nationalization. When Darth Vader and Boba Fett arrived in the Bespin system, Calrissian sought to retain its independence by making a covert agreement with Vader to assist in the capture of Luke Skywalker. Lando fulfilled his part of the agreement, which was altered to include testing the carbonite-freezing process (normally used to prepare Tibanna gas for shipment) on Han Solo. However, as the terms of the deal worsened and it became clear the Empire intended to take control of the floating city regardless, Lando ordered the evacuation of the city and assisted the Rebels in their escape.
In preparation for the attack on the second Death Star, Calrissian was promoted by the Alliance to general. At the Battle of Endor, General Calrissian commanded the Rebel starfighter contingent as Gold Leader from the cockpit of his old ship, the Millennium Falcon. Calrissian, along with Wedge Antilles and Tycho Celchu, led the starfighter assault into the battle station to destroy it. After evading TIEs and having close run-ins with the station's superstructure, Calrissian fired the Falcon's concussion missiles into the Death Star's reactor core, destroying the station; for the second time that day, Calrissian rode a fireball from inside an Imperial structure to safety. The destruction of the station, along with Luke and Anakin Skywalker's victory over the Emperor, effectively sealed the fate of the Empire, and Calrissian was hailed a hero.