Lando apparently wanted to be a gambler and con artist from an early age. And he succeeded well enough to win fortunes (and lose them), starships, robots, and a mining colony. He also smuggled part time and even tried his hand at legitimate shipping.
He had an entreprenurial streak, but while on the surface he seemed selfish getting dragged into other people’s fights slowly helped mature him. The game to let him win Cloud City was rigged apparently (but not by him) in order to let him win. Yet being administrator made him responsible for the citizens. When Vader showed up looking for his buddy Han, Lando knew that the best thing for the citizens was to give him up. But how was he to know that Vader never intended to honor the deal? And so, he went for a rescue of Han’s friends, then Han, pausing only long enough to warn the citizens the Empire was taking control.
Lando was loyal, and even though Han had caused him a lot of trouble in the past, it was never intentional. His own guilty concious sent him out to find and rescue him even after they escaped Cloud City.
Ultimately, Lando would become a General in the Alliance, lead the final attack of the starfighters at Endor and fire the fatal shots that destroyed the Second Death Star.
AKA: Drebble (basically this was identity theft, he and the real Drebble hated each other.)
Not much is known about them except he grew up in the Corellian system and definitely had a Mother. But he did find a wife through unconventional means. He was looking for a rich woman who would put up with (and back) his expensive schemes when he stumbled onto Tendra Risant. While not immediately rich (she had a trust fund) he did fall genuinely in love. They would marry and have a son, Lando Jr, who they called ‘Chance’.
In many ways however, Han, Luke, and Leia were also his family with the kids practically knowing him as an Uncle.
Han Solo was his most famous friend and also the one who got him in the most trouble. Not that he ever meant to, but somehow when Han was involved he often ended up with the short end of the stick somehow.
Vuffi Raa was another good friend, the small unique droid was created by a race of ‘sentient starships.
He continued working closely with Lando Calrissian and for a time actually smuggled along with Salla Zend.
Kyle Katarn was fortunately a friend, which is a good thing because while he wasn’t in charge of Cloud City he did have interest there, and investigating the gangs taking over got Lando caught by them on Nar Shaddaa.
Zak and Tash Arranda were two kids with Jedi Potential who stumbled on an Imperial plot on Hologram Fun world while Lando was there looking into investing. Fortunately for them, he proved friend enough for a rescue.
Lando had various other smuggling acquaintences, but its debatable how many he could truly count on.
Lando did not set out to make an enemy of the Sorceror of Tund. However when Gepta’s manipulations of him backfired, he set out to destroy Lando. In the end however Lando won.
Shanga and his men weren’t really Lando’s enemies, he just inherited them from his pal Vuffi over a misunderstanding. They thought he was the organic being who destroyed their world. Until it was sorted, he often got caught int he crossfire.
In all probability Vader himself gave little thought to him. But no doubt being forced to turn Han in and abandoning Cloud City left Lando thinking of him as the enemy.
Lando had no idea how convinced she was that he would pursue her. But he did destroy her antics on Cloud City that involved the brutal torture and murder of the droid workforce.
Lando’s earliest aspirations apparently were just ‘be the best gambler’. He loved the thrills and the winning. He also had no problem conning people out of their money. Presumably he targeted the rich (not much to fleece from the poor for one thing.) He went on to be a smuggler as well.
But while his primary goals were selfish, he still made friends along the way and still found himself helping out. His helping out the Sharu earned him some consideration, his saving the Oswaft made him rich. These were side effects rather than goals.
Still, while putting himself in harms way for profit was usually the modus operandi, he did do it for friends as well. He rescued Han from Boba Fett once before he even knew him, convinced a pirate ex-girlfriend to pay off Fett to save Han’s Ex girlfriend from the same bounty hunter and even rescued Zak and Tash Arranda from Hologram Fun World with no profit to himself. He could’ve fled when the Empire decided to make an example of the Smuggler’s Moon of Nar Shaddaa but instead stayed to fight. When he landed Cloud City, he had to balance the desire to gamble (but not take advantage) and the needs of the populace. He didn’t turn on Han for greed, but to save the City’s citizens from Imperial takeover and when that failed, warned them.
Conscience stirred at being forced to choose between equally bad sacrifices, he now found himself working with the Rebellion and using old contacts to help them and find Han.
For a man who preferred a certain culture, it would’ve been no small sacrifice to go undercover in the dregs of Jabba’s court for the rescue. After that instead of jaunting off to gamble for credits or riches, he was gambling his neck against the Empire and Death Star 2.
While he still enjoyed gambling, he largely went back to being an entreprenuer and investing. Once more he found himself seeking to save and help Cloud City, even to the point of poking around Nar Shaddaa to find out who the kingpins taking over were when he had no authority and needing a rescue by Kyle Katarn.
Even while pursuing his own interests and having given up the rank of General, Lando continued to be available when the New Republic needed his aid.
Stories starring Lando Calrissian
The Empire Strikes Back Radio Drama by Brian Daley
Return of the Jedi Radio Drama by Brian Daley
(Note these radio dramatization of the movies includes extra and extended scenes not available elsewhere. Also star the original actor as the voice of Lando.)
Classic Marvel Comics:
regular issues 83-197
regular issues 46-79
Lando Calrissian Trilogy by L Neil Smith (this is set between Hutt Gambit and Rebel Dawn)
Han Solo Trilogy by A.C. Crispin specifically:
Han Solo: Hutt Gambit
Han Solo: Rebel Dawn
Underworld: Yavin Vasillika (Dark Horse Comics)
Scoundrels by Timothy Zahn (Check out an Audio Excerpt!)
Galaxy of Fear Series – by Whitman – Cameo only
Shadows of the Empire: Evolution (Dark Horse Comics)
Tales of Jabba’s Palace (various short stories)
Thrawn Trilogy by Timothy Zahn
Heir to the Empire
Dark Force Rising
The Last Command
Dark Empire – Dark Horse Comics – Also Audio Adaptation where Billy Dee Williams Reprises the role
Dark Empire2- Dark Horse Comics
Empire’s End – Dark Horse Comics
Jedi Academy Trilogy by Kevin J. Anderson
Champions of the Force
Jedi Outcast (game)- Cameo by Lando where Billy Dee Williams Reprises the role
Black Fleet Crisis by McDowell
The New Rebellion by Kristin Kathryn Rusch
The Corellian Trilogy by Roger Allen McBride
Ambush at Corellia
Assault at Selonia
Showdown at Centerpoint
Thrawn Duology by Timothy Zahn
Specter of the Past
Vision of the Future
Young Jedi Knights by Kevin J. Anderson and Rebecca Moesta
Trouble on Cloud City
Crisis at Crystal Reef
New Jedi Order Era by Multiple authors
Chewbacca (tribute) – Dark Horse Comics
Legacy of the Force Series by multiple authors
Millenium Falcon by James Luceno
Fate of the Jedi series by multiple authors
Crucible by Troy Denning