Greatest smuggler in the galaxy, swindler, gambler, businessman, and hero. These are the titles of Lando Calrissian. He took down a Death Star twice the size of the original, built a thriving mining business from nothing, and provided Han with the fastest hunk of junk in the galaxy. Star Wars wouldn’t be what it is today, without Lando Calrissian.

“The audience was so enamored with Lando, they could forgive Lando for anything,” stated Billy Dee Williams in an interview. “If you’re able to play a character that can be sort of a bad guy but has redeeming qualities, those are the best characters to play. That was a great challenge to me, to make him palatable, and it worked.”

Billy Dee Williams is Lando Calrissian. And now, Donald Glover is too. “This is probably one of my favorite experiences ever,” stated Glover in a 2017 interview. “For working under, like, a huge conglomerate, it’s actually been quite an enjoyable, artistic thing. I get to play him in a way that I think is honest and true and cool. And it’s great ’cause I didn’t have to write anything, I’m focused strictly on being this guy. And I really respect him and I respect the actor who played him before. I’ve learned a lot about this character, so it’s actually been really fulfilling and nice to just turn off everything else and focus on just being someone.”

Lando isn’t, however, your normal run-of-the-mill character. From playing in sabacc games during his tweens to leading the Rebel Alliance towards a major victory, here are 25 dark secrets you’ll want to know about Lando Calrissian.

25 Sabacc High

Lando Calrissian didn’t become a sabacc legend overnight. He spent years learning from others and perfecting his game. As a teenager, Lando was known to skip classes, heading out to the local cantinas to wager his bets for the day. During one such game, Calrissian learned the hard way regarding getting his winning hand onto the table. Gloating over his victory, his opponent threw down first and took the hand

In his mid-twenties (as an experienced gambler) Calrissian won a YT-1300 freighter in a high stakes game of sabacc — the Millennium Falcon from Cix Trouvee. Lando would later lose the Falcon to Han Solo, during another high stakes game. Calrissian was so confident with his hand, he threw in any ship from his inventory into the pot. Whether or not Solo cheated on the hand has never been determined.

24 Boosting The Wrong Ship

Thanks to the Lando Calrissian comics by Marvel (Lando #1), bits of his past has been included into canon. Within these tales is a mishap that almost cost Lando his life. Deep in debt due to gambling loses, Calrissian and Lobot were forced to take a job boosting a luxury yacht ship. In exchange for the ship, Lando could keep what was on it.

Little did Calrissian know, but the ship was Emperor Palatine’s personal yacht.

Three Imperial Star Destroyer’s blocking his path, however, got Lando up to speed on his dire circumstances. Pulling an impossible maneuver (because like Han, you never tell Lando the odds), he managed to wiggle his way past the blockade. But even after such a daring victory, Lando and Lobot’s troubles were just beginning.

23 Sweet Talking Ladies’ Man

Lando Calrissian’s personality resembles that of Billy Dee Williams. Much like how Han Solo and Harrison Ford are one. Lando loved to sweet talk the ladies, flashing his good looks and charm to get his way. And that’s not just EU material either. Lando immediately butters up Sabine in Star Wars Rebels. And who can forget his lines delivered towards Princess Leia in Empire Strikes Back.

Prior to taking on the role of Lando, Billy Dee had already earned himself a reputation of being suave and a ladies’ man. These characteristics were carried over into Calrissian, from the cape to his deviant and charming smile. Billy Dee hasn’t been shy about stating how he owns the character, and he shouldn’t be. But allegedly, him and Donald Glover are on good terms regarding him taking on the younger version of Lando Calrissian.

22 No Hokey Pokey

“Hokey religions and ancient weapons are no match for a good blaster at your side, kid.” This is Han’s famous line from A New Hope spoken to Luke regarding the force. Like Han, Lando used to feel the same way — until he came face to face with the power of the Sith.

After boosting Palpatine’s personal luxury yacht, Calrissian and his gang of misfits began dividing up the treasures to be had. What neither Lando nor anyone could have known, is that the Emperor had ancient Sith relics being guarded on the ship. To the untrained eye, they looked like ordinary artifacts. After securing the room, two of Lando’s crew mates became corrupted by the artifacts, forcing Lando and Lobot to eliminate them.

Lando bargaining with Darth Vader in Cloud City, was a result of him witnessing the power of the dark side. He knew he had to play along until an opportunity presented itself. Then Lando could make his move.

21 Riff Between Mates

Buried within the tales known now as Legends there’s a tale that might show up in Solo: A Star Wars Story, or at least an adaptation of the original tale. Prior to taking over Cloud City and after Calrissian lost the Millennium Falcon to Han, Solo took a job he shouldn’t have.

The gig involved stealing from Jabba the Hut, in which the bounty would be split between Lando, Han, and Solo’s lover who was orchestrating the heist. Han would get played, leaving him with nothing. This also meant he had nothing to give to Lando. Calrissian cut ties with Han after that and began to turn his life around for the better. Their reunion at Cloud City was the first time they had seen each other since their falling out.

20 Tricked-Out Blaster

Lando had two primary blasters he used. The first was an X-8 Night Sniper blaster pistol manufactured by BlasTech Industries. It featured a computerized scope, along with silencer functions. The X-8 was a popular choice amongst bounty hunters like Latts Razzi and C-21 Highsinger. During Calrissian’s smuggling days, the X-8 Sniper blaster was his go-to weapon of choice.

The second blaster Lando owned was a Vitiator pistol (similar to the DH-17 blaster pistol), which he won in a game of Six-Card Gizka Limit from a spice-drunk Aybarian diplomat. At one point, Lando thought of giving the Vitator to Han and Leia as a gift for baby Ben Solo but was advised by Lobot not to. Which was probably a good idea considering Ben became Kylo Ren.

19 Fashion Aficionado

There’s a long-standing theory which focuses on who’s clothes Lando was wearing at the end of Empire Strikes Back. Considering Calrissian’s taste in clothing (the infamous cape he wore in Cloud City), one must wonder why his change of clothes look just like Han Solo’s clothing. The first theory states they are Han’s clothes, since Lando wasn’t exactly packing a to-go bag while racing onto the Millennium Falcon.

The second theory, presented by YouTuber Jon Solo, states that the clothes Lando changes into were originally his to begin with. When Han won the Falcon from Calrissian, he acquired the ship and its belongings. This would have included clothing. So, Han was actually wearing Lando’s clothes the whole time. Personally, theory number 2 makes the most sense, and that the pants were always Han’s.

18 Scoundrel Tall Tales

Lando Calrissian was a natural smooth talker who enjoyed boasting of his accomplishments. But at times, it was hard to discern between fact and fiction. Much like the tall-tales which flow from a fisherman’s loose lips.

Lando took out two Imperial Star Destroyer’s — at the same time.

The tale sounds made-up but it’s actually true. After escaping gravity mines which were holding down Emperor Palpatine’s boosted yacht the Imperialis (that Lando had stolen), he ran into a blockade of Star Destroyer’s.

Two Star Destroyer’s hooked onto the Imperialis with their tractor beams, but Lando got Lobot to feed the coordinates of the tractor beams into his piloting computer. Lando then locked Captain Conro’s Star Destroyer’s tractor beam onto Captain Shan’s ship. This caused both ships to collide with one, damaging both Star Destroyer’s and allowing the Imperialis to break free.

17 Too Legit To Quit

Following Lando’s loss of the Millennium Falcon to Han Solo in a high stakes game of sabacc, Calrissian rethought his life’s goals. For a time, he stopped playing the high roller games and embarked on creating a legitimate business for himself. Star Wars Rebels provided insight into this part of Lando’s life, during his time on Lothal.

But luck wasn’t done with Lando yet

Calrissian found himself in another high stakes sabacc game with the Baron Administrator of Cloud City. Trying to out bet the experienced Lando, the Baron put his title in the pot. Which Lando won. Seizing the opportunity to be a legit businessman, Calrissian hired Gev Hessan to help him smuggle in everything he needed. As the Baron Administrator of Cloud City, Lando often hired refugees to be on his staff. Helping those in need to get back on their feet.

16 True Best Friend

Nope, were not talking about Han Solo, but rather the infamous sidekick Lobot. Lo (as commonly called by those closest to him) is a human with an implant known as the AJ6 cyborg construct. He at one time was a slave for the Empire, running battlefield calculations for them.

Lando trusts and respects the advice of his dearest friend.

Lobot came into the service of Lando during the height of his smuggling and gambling days, in which the two became good friends. Lando trusts Lobot with his life as Lo is loyal to Calrissian no matter the circumstances the two found themselves in. Even after Lando joined the rebellion, Lobot was always close by, ready to do anything while providing wisdom and advice to his comrade-in-arms.

15 Collector Of Puffer Pigs

Growing up on an Outer Rim planet where mining was the normal way of life, Lando knew (prior to owning Cloud City) that mining would be his ticket out of the scoundrel life. Star Wars Rebels worked this arc into Disney’s canon, by introducing Calrissian and his farm of Puffer Pigs. What Lando knew, but most didn’t, was that Puffer Pigs were adapt at sniffing out minerals. This saved massive amounts of time and resources when running a mining operation.

The only downside to Puffer Pigs is that they expand tremendously when frightened. The Ghost crew found this out first hand after Ezra let a Puffer Pig out of the crate and it encountered Zeb while exploring the ship. Zeb’s appearance caused the pig to blow up and block off half of the ship, almost leading to the Ghost being captured by the Empire.

14 Near Termination Through Writers Block

Despite Lando Calrissian’s popularity following the original trilogy (thanks to Billy Dee Williams), writer Kevin J. Anderson almost pulled the plug on his iconic character. After appearing in several books (now part of the Legends series’), there was talk regarding Lando’s future within the books.

Anderson felt that Calrissian’s character had “run his course.”

Was it writers block or a natural arc? Thankfully, we’ll never know because Lucasfilm decided against the elimination of Calrissian’s character. Thanks to some quick thinking, Lando and his tales were brought into the Disney canon with relative ease. Although Lando wasn’t in the current running trilogies, his character received its own standalone comic through Marvel. Not to mention, Calrissian is sure to play a big role in the upcoming Solo: A Star Wars Story movie in the summer of 2018.

13 Evading Imperial Bounty Hunters

Lando had put himself in a tight spot, the “All In” kind of spot. He needed lady luck to come through with the save. After escaping the blockade of Star Destroyer’s in Palpatine’s ship the Imperialis, Lando retreated into deep space. But what he didn’t know at the time was that Palpatine had sent a bounty hunter after him named Chanath Cha.

Little did Palpatine know, but Cha, Lando, and Lobot all had history together.

Cha’s specific orders were to secure the ship and eliminate its thieves or destroy the vessel as an alternative. Being that Cha wasn’t about to take out “old friends,” she agreed to give Lando and Lobot safe passage — as long as she followed through with her orders to eliminate the ship and its contents.

12 Fancy Flying Equals Quick Promotions

Another tale Lando often likes to recount is the one concerning the Battle of Taanab. Most of the story has become part of the EU now, but thanks to Calrissian’s line in Return of the Jedi, the tale lives in canon too. Lando was chilling in a casino on Taanab, in between jobs, when he found himself in the middle of a pirate heist.

Claiming he could take the pirates down single-handedly, a brewery owner named Gathal Danager took Lando up on his bet, putting his brewery deed into the pot. Using his recently acquired cargo full of nets, Lando entrapped the pirate’s ships, eliminating 19 vessels all by himself. His popularity grew after that, and word spread around the galaxy. Leading to his promotion within the Rebel Fleet prior to the Battle of Endor.

11 Returning Home

After the Battle of Endor and around the time of the Jakku battle, Lando returned to Cloud City. The mining operation still had a small splinter cell of Imperials who hadn’t been removed yet. Calrissian and Lobot trapped the stormtroopers, and one officer, in a sealed room with poison gas. But the effects were useless on their armor.

Lando offered the stormtroopers a hot meal (and their lives) if they surrendered.

He then ordered the doors to open. All but the officer came out and surrendered. The Imperial offficer put up a fight, forcing Lando to shoot him with his Vitiator blaster. Once the threat had finally been removed, Lando spoke to Lobot Han’s infamous line from The Force Awakens, “we’re home.”

10 Who’s The Greatest Pilot?

Han Solo boasts often of being the greatest pilot in the galaxy, and this might be true. However, don’t count Lando Calrissian out. He played a crucial role in blowing up the second Death Star and earned a reputation prior to that at the Battle of Taanab.

In the EU, Han taught Lando how to fly.

But in canon (to date) Lando earned his stripes on his own. Personally, I believe them to equals. Going off the Star Wars Legends books and Disney’s new canon, both pilots have shown to have exceptional skills. Concerning beating the odds, Han Solo might have a slight upper-hand over Lando. According to Solo, Han was the original best pilot in the galaxy. But what did everyone else think?

9 A Rebel Before The Rebellion

Lando is a savvy guy, never passing up an opportunity to connect and network with like-minded individuals. In Star Wars Rebels, he met the infamous Ghost Crew, working side-by-side with them. Naturally, he suckered them in to helping him — by taking over their droid Chopper.

After the job was finished, Calrissian went back on his word about paying the crew their credits. But only because he noticed Chopper stealing several gallons of fuel of his farm on Lothal. Hera, who wasn’t pleased with how Lando did business (or how he messed with Chopper), told him he owed the crew a favor. Lando happily agreed, knowing he was already caught up in something bigger than him or his so-called business operations.

8 Violence As A Last Resort

Despite seeing Lando blowing up Death Stars and leading armies, he actually prefers to solve problems through non-violent methods. Usually this involves plenty of sweet talking, but the odds are in Lando’s favor. Because more often than not, he finds a better solution through talking and negotiating than through fighting. But don’t consider him weak just because he avoids the usual fights. When push comes to shove, Calrissian will have his way, even if that means blowing things up and taking his opponents out.

This aspect of his personality is one of the many reasons Lobot stays loyal to Lando. He respects the fact that he doesn’t resort to violence right off the bat, taking alternative approaches instead. Even if they get him in more trouble than he was previously in.

7 Beef With The Hut

Being an independent owner and operator, along with scoundrel and smuggler, Lando couldn’t avoid issues with Jabba the Hut. Most of the tales are now part of the Star Wars EU, but they still provide insight into Calrissian’s daily operations. The problems Han created with Jabba, were part of the reason as to why Lando cut ties with him.

Lando infiltrating Jabba the Hut’s fortress on Tatooine in Return of the Jedi was to save Han, and end Jabba’s reign. Calrissian didn’t shed any tears knowing Jabba was eliminated above the Sarlacc Pit. In fact, it likely increased his operations tenfold down the road. Boba Fett taking Han to Jabba’s palace was simply icing on the cake for a plate of revenge.

6 Better A Scoundrel Than A Clone

Most directors and producers will go through several movie scripts and various adaptations before settling on the final cut. The Empire Strikes Back was no exception to this rule, and it’s a good thing changes were made.

Originally, George Lucas wanted Lando to be a clone.

Yep, a clone. This was of course long before he had the idea to make the prequels into movies themselves. Lando was supposed to be a clone that came from a planet of clones. He was slated to be a leader amongst refugees that had been affected by the war. Thankfully, that idea was scrapped, and the Billy Dee Williams version was born. Although, it would be interesting to see Lando as a clone, yet potentially scary for the female population.