A long time ago, Lando had a chance to offload one of the worst ships he'd ever seen on an unsuspecting friend, someone he hated, actually, a scumbag pirate named Han Solo. Playing up his considerable charms and laying down the con, he thought he had it made. But then he won the hand, kept the ship, and his life just kept getting worse.
One day he found himself on the desert world of Tatooine, and finding little resembling civilization, he holed himself in a cantina and proceeded to drink himself into heavy debt. Thankfully he was smart enough to stay out of Hutt business, but that was about the best Lando could say about himself.
He began listening around as the dubious individuals who came to the establishment with its terribly chintzy music chattered about locals who wanted off this world, and could he blame them? All he needed was a reason, something to give him a little hope.
Blundering his way through the rabble was a farmboy, who didn't seem liked he knew the difference between a hyperdrive and a cargo hold, but Lando suddenly realized this was exactly the opportunity he'd been waiting for. The boy sounded panicked, making a poor effort at masking it, and desperate for any help. Fortunately Lando was available to rescue him from his plight.
Before he knew it, though, the situation degenerated. The boy and his passengers, an old man and two droids, had attracted Imperial trouble, something Lando had always been smart enough to stay away from, which meant their departure looked more like a hasty retreat, which was about as dignified as things had been going for him, so he didn't sweat it too much. He decided to play it cool. The old Lando was returning.
Worse came to worst, and Lando found himself challenging everything he'd ever thought about the galaxy. Naturally, he became a hero.