The galaxy within the Star Wars universe may be filled with plenty of dashing and heroic characters, but you'd be hard-pressed to find a personality more suave, charming, and downright debonair than the one and only Lando Calrissian. Whether portrayed by his originator, the iconic Billy Dee Williams, or in his younger years by Donald Glover, Lando is one of the most magnetic characters in the entirety of a galaxy far, far away.
To date, Lando has appeared in four of the Star Wars films: Empire Strikes Back, Return of the Jedi, The Rise of Skywalker, and Solo: A Star Wars Story, as well as countless expanded works. For the sake of this list, we'll be taking a look at his cinematic appearances, and recapping his smoothest moments.
"I hate you." "I know."
The relationship between Han Solo and Lando Calrissian, the longtime friends turned enemies turned friends again, is one of the most iconic parts of the Star Wars franchise. Therefore, it's only fitting that the first quote on this list is one that perfectly encapsulates their rapport.
Though Han may be more famous for his response of "I know" to Leia Organa's declaration of love, it's Lando's passionately playful declaration of hatred in Solo: A Star Wars Story that chronologically earned the same flippant response first. There's a fine line between love and hate indeed.
"Hello. What have we here?"
From the moment Lando enters the scene in Empire Strikes Back, his smooth, total lady's man persona immediately comes to the fore when he meets Leia Organa. With that charming smile and natural flirtatious ease, Lando greets a clearly uninterested Leia, but he just looks and sounds so darn good while doing it.
It may be the first time that Lando expresses a bit of interest in the princess, but it certainly won't be the last.
"I don't like it. I don't agree with it. But I accept it."
Donald Glover's performance in Solo: A Star Wars Story perfectly embodied much of what made Lando Calrissian an instantly iconic character. One such aspect is Lando's cool and calculating businessman side, even though it's often paired with that same cheeky, charming demeanor.
In Solo, in particular, Lando finds himself in one uncomfortable situation after another, particularly with the wily Tobias Beckett involved. But he's willing to put his own opinions aside for the sake of the job, just as any cunning businessman would.
"I know what she means to you. I'll take good care of her."
Long before Solo revealed the complex history of how the Millennium Falcon changed hands between Han and Lando, the original trilogy still touched on the emotional significance of the ship for both men in subtle ways. Han was understandably wary of entrusting his beloved ship to Lando after everything they'd been through so far in the trilogy.
But Lando was quick to switch into his smooth, reassuring mode, lovingly promising to take the best care of the prized hunk of junk and winning Han over in the process. Well, for the most part.
"We had each other. That's how we won."
The return of Lando Calrissian was highly anticipated in The Rise of Skywalker, but much like the rest of the film, it turned out to be a lot of hype for very little payoff. Even still, Lando managed to be just as smooth and charming as ever in the little screentime he did get.
Reflecting on how the Rebels had been able to defeat the seemingly endless massive powers in the Empire, Lando credited their strength to their relationships with each other - a true sign of character development.
"You might wanna buckle up, baby."
The relationship between a young Lando and his droid sidekick, L3-37, was one of the unmistakable highlights of Solo: A Star Wars Story. The tenderness between man and droid was something not depicted elsewhere in the Star Wars galaxy, and it made all of their moments together - whether funny or serious - mean that much more in the long run.
The simple inclusion of Lando referring to L3 as "baby" also spoke to the closeness of their relationship, and the length of their history together, providing some much-needed insight into Lando's personality and history.
"Princess, we'll find Han. I promise."
With the way Empire Strikes Back ends, the galaxy is in more dire straits than it has been at any other point in the trilogy so far. Luke has just learned Darth Vader is his father and has had his hand cut off in the process. Han Solo has been captured and frozen in carbonite, leaving Leia alone and heartbroken.
With just a few simple words of reassurance, Lando is responsible for instilling a sense of hope back into the galaxy when it truly needs it most.
"Everything you've heard about me is true."
Few characters in the world of Star Wars act like their own hype man in quite the way that Lando does. But honestly, who could blame him? One of the most mythic figures in the franchise, Lando's legacy truly precedes him, no matter where he goes or what time period the story is set in.
So yes: Every story you've heard about Lando is true. It's true within the universe of the film when he tells it to Han, and it's probably true as a tongue-in-cheek remark to an audience member, too.
"Give Leia my love."
The unrequited love Lando has for Leia is something we have briefly touched on before, but The Rise of Skywalker makes it clear that this flirtatious side of Lando is something that has lasted even after all these decades. Lando doesn't get many lines in the film, but he does get to use one of them to restate his love for Leia.
It's a shame that the two never get to have a proper reunion, especially since Lando talks of spending time with Luke on a prior adventure. But all the same, Lando is as smooth as he ever was, even after all these years.
"You look absolutely beautiful. You truly belong here with us among the clouds."
Sorry, Han, Anakin, Ben, and others: No flirtatious line in the entirety of Star Wars could ever dream of matching the swoon factor of Lando's openly flirtatious attempt at flattery in Cloud City. After Han and Leia have settled into Bespin, Lando pays them a visit and pays the newly outfitted Leia a truly outstanding compliment.
Han and Leia are the great romance of the Star Wars universe, and there's no denying that. But honestly, we wouldn't have blamed Leia for falling for that line. It's just so darn good.