Androgyny: The Enduring, Intergalactic Cool of Billy Dee Williams

As the legendary actor returns to Star Wars, he talks about his masculine and feminine sides, the legacy of Lando, and how after 82 years he’s never lost his style.

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MATT MILLER AND PHOTOGRAPHY BY AARON RICHTER

NOV 26, 2019 (esquire.com)

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Aaron Richter

Billy Dee Williams’s guide to being cool involves one simple step: “Be yourself.” He tells me this while sipping a Tito’s vodka neat with a little bit of Emergen-C sprinkled into it (a perhaps healthier choice than the Colt 45 with which he will be eternally associated after a string of ads for the drink in the ’80s). “I never tried to be anything except myself. I think of myself as a relatively colorful character who doesn’t take himself or herself too seriously.”

That’s a humble way of putting it. For nearly half a century, he’s been one of the coolest actors ever to appear onscreen. As Lando Calrissian, the suave, cape-wearing hero of the Star Wars universe, he’s immortalized as the quintessential figure of intergalactic chic. But beyond the sci-fi saga that has captivated generations, he’s a prolific actor and artist—he even designs his own clothes, showing up to our early-October photo shoot in a beautiful brown belted overcoat he made himself. When he starts telling me about what it takes to be cool, we’re at the beginning of our interview at the Russian Tea Room in midtown Manhattan. He’s already had a long day of graciously appeasing legions of fans at New York Comic Con. Williams hasn’t been to the restaurant in “a hundred years,” he says, but it was a regular haunt of his as a 20-something Broadway actor. (He lived a few blocks away before moving to California in 1971.) 

The place hasn’t changed much since then; his favorite dish, the chicken Kiev, is still on the menu. In fact, he was so excited about this dish that we called the restaurant beforehand to make sure they could still make it. And, of course, I order it, too, because if Williams says you try the chicken Kiev, only a fool wouldn’t order the chicken Kiev. Over the course of our nearly-four hours of drinking and eating, we have more vodka, a bottle of red picked by Williams, caviar, a cheese plate, and a boozy dessert. Williams knows how to entertain. He knows how to eat. And he certainly knows how to drink. Sitting to my left in a plush, red booth, he seems like he runs the place, like it’s one of Lando’s regular joints in a far off galaxy. He’s kind to the fawning restaurant staff. And, when a group comes in, wearing what appears to be attire from a wedding or a formal party, Williams notes—always with an eye for style—that they look chic. Some of the paintings that’ve inspired his own artwork cover almost every inch of the green walls—like the Tamara de Lempicka portrait of a woman reclining opposite us. Williams grew up about 50 blocks north of here, on the edge of Harlem, where he learned what it meant to be cool from the guys on the streets who had “a little more smoothness about them.” After first appearing on Broadway as a boy, he went to school for painting, something he’s done regularly and to much acclaim throughout his acting career. Though, he admits, he doesn’t paint as much as he should these days.

What haven’t diminished at age 82 are his style, his confidence, and his effortless charm. In a simple tan button-up, with his hair slicked back, Williams continues his analysis of cool: “And you see I say ‘himself’ and ‘herself,’ because I also see myself as feminine as well as masculine. I’m a very soft person. I’m not afraid to show that side of myself.”

When I point out that Donald Glover talked about that type of gender fluidity when playing a young Lando in 2018’s Solo, Williams lights up. “Really? That kid is brilliant—just look at those videos,” he says, referencing Glover’s “This Is America” (as Childish Gambino).

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Aaron Richter

Although he will forever be known as Lando, Williams is proudest of his Emmy-nominated performance as Gale Sayers in the 1971 TV movie Brian’s Song. “It was a love story, really. Between two guys. Without sex. It ended up being a kind of breakthrough in terms of racial division,” he tells me. The same could be said about his portrayal of Lando in 1980’s The Empire Strikes Back, which marked the inclusion of a complex black character in a genre that was—and remains—notoriously white. In fact, over the summer, when he was at Disney’s D23 Expo in support of the upcoming Star Wars: The Rise of Skywalker (for which he is reprising his iconic role), he hung out with the Rock and Jamie Foxx, both of whom said their careers are indebted to Lando. “The Rock calls me the OG,” Williams says. “What I presented on that screen people didn’t expect to see. And I deliberately presented something that nobody had experienced before: a romantic brown-skinned boy.”

J. J. Abrams, who is directing the conclusion to the Skywalker saga, told me via email that Williams’s charisma and charm are unmatched. While Abrams says he can’t begin to imagine what it must have been like for people of color to see a character like Lando onscreen in 1980, he recognizes Williams’s place in film history. “Lando was always written as a complex, contradictory, nuanced character. And Billy Dee played him to suave perfection,” Abrams says. “It wasn’t just that people of color were seeing themselves represented; they were seeing themselves represented in a rich, wonderful, intriguing way. Also, he has the best smile in Hollywood.”

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Lucasfilm

Before he was even cast, Williams was a fan of George Lucas, beginning with 1971’s THX 1138. And director Irvin Kershner thought the actor had the right style for Lando, so Williams didn’t even have to audition for Empire. “He knew I could pull off someone who was likable and charming. The most interesting characters are those who are dubious . . . but you want the audience to really fall in love with them,” Williams tells me. (For the record, he understands why Lando had to double-cross Han and Leia. “He was up against Darth Vader. I don’t blame him for what he did.”) Kershner went to Williams’s house to persuade him to be in the film; it didn’t take much, the actor says, to get him to appear in one of the most anticipated sequels of all time. On set, he befriended costars Carrie Fisher (who he says had a brilliant mind) and Harrison Ford (whom he still considers a dear friend), and he avoided workplace gossip. “As far as I’m concerned, I mean, I don’t care what people are—if they’re fucking each other and they’re sucking each other, whatever they’re doing, that’s fine with me. I don’t care,” he says of Fisher and Ford’s romance, as described in her memoir.

If they’re fucking each other and they’re sucking each other …that’s fine with me.

Now, for the first time since 1983’s Return of the Jedi, he’ll play Lando once again. Between Jedi and the events of the new trilogy, Williams says, “I always imagined Lando being like Steve Wynn, running Las Vegas. Because he’s a gambler. But he was a bit of a showman, a bit of an entrepreneur. That’s how I see Lando. I never necessarily saw him as a general running around shooting things.”

We don’t know exactly what’s behind Lando’s return to the franchise, but trailers show the hero back in the cockpit of the Millennium Falcon. Stepping onto that set again, Williams says, was cool—but also work. “You’re bringing something that helps move the vision that the director or producer or writer is looking for. I’m there not only for myself, but I’m there to help them bring their project to life in a way that they’re looking for.”

He admired the atmosphere Abrams (or the young mogul, as Williams calls him) created on set. “At the end of the day, there’s music that’s turned on. Everybody’s dancing and singing,” Williams says, reminding me that he once played himself in an episode of Lost. His only worry in returning to the iconic character was that he still had the fire to bring a powerful performance to the conclusion of the saga, “Do I have that same hunger, excitement, that I had years earlier?,” Williams asked himself. “This is a very difficult time for me, as far as age is concerned. When you get to be a certain age, whether you want to think about mortality or not, you think about it.”

When our food finally comes, Williams takes a bite of the chicken Kiev he remembered so fondly from his younger days, and makes a comment that could work as a good thesis statement for our entire conversation, or the nature of nostalgia like Star Wars taking hold of this moment in popular culture: “An original moment is tricky. Because you’re really trying to recall or remember your palate, your sensibility, trying to recapture something that happened a long time ago,” he tells me. “And when you anticipate it, you think you’re going to be in that moment. I’m right at that moment. So what I’m tasting is not that moment. I’m tasting this moment. And I’m happy about this moment but it’s not what I remember.”

In preparation for his return to Star Wars, Williams went on a strict healthy diet, and shared videos of himself training in a boxing gym. “When I have to go to work, my ego tells me I want to look pretty good. I don’t want to look bad. I don’t want to look like a slob,” he says, even though none of these have been adjectives ever associated with Billy Dee Williams. But, he hopes the videos of himself training serve as a reminder that people his age are capable of taking care of themselves, that there’s a way to go through later years of life happy and healthy.

Billy Dee Williams@realbdw

Having built his career playing pivotal examples of TV and film diversity, Williams is well aware of what the new trilogy’s young leads went through—namely, racism and sexism from online trolls—when they were launched into the spotlight. “You’re always going to have people making stupid comments,” he says. “One deals with indignities all the time. Do you sit around with vengeance in your soul? You can’t do that. I’m not forcing people to listen to my point of view, but if I can present it in some creative fashion—I’m the painter, tweaking, adding, contributing, putting in something that you haven’t thought about, maybe.”

Thinking about struggles in the world around him, Williams mentions his encounter with Donald Trump at an event in the ’80s: “He was very charming. And very good at being charming. You know the story of Narcissus? Who looked at himself in the water, fell in love with himself, and then fell in and drowned? I mean, this might be one of those kinds of things.”

As for what’s next, Williams is writing a memoir. And he also has a collection of 300 paintings that he says is his legacy.

Billy Dee Williams

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So is this the end of Lando? Williams says he doesn’t know exactly how the story ends for his hero. He loved the scripts he read, he’s proud of the work he did, but, “another thing about movies, there’s a lot of editing and cutting,” he says, laughing as he eats a cup of passion-fruit sorbet with a shot of vodka poured on top. For me: a double espresso with Grand Marnier that he insisted I try (I didn’t sleep that night).

By this time, we’re both warm from the hours of drinking—I’m astonished I was able to keep up with Billy Dee Williams, even if he’s 82 years old. And before he says goodbye, he wants to sign one more autograph in a long day of doing just that. He realizes that during the shoot and convention, where everyone was clamoring for his name, written by his own hand on a piece of paper, I never asked for one. That’s not my style, I tell him, this dinner and story is memento enough. He grabs my notebook that I haven’t opened once during dinner, signs his name with the note, “Nothing but the truth.” And he gives me a hug.

Back to the question at hand though: Is this the end for Lando Calrissian? Williams has an answer in his own wry way.

“It’s a conclusion—certainly it depends on how much money is generated. That’s when they determine where’s the conclusion,” he says with a wink. “The one thing about show business, you can resurrect anything.”MATT MILLER Culture EditorMatt is the Culture Editor at Esquire where he covers music, movies, books, and TV—with an emphasis on all things Star Wars, Marvel, and Game of Thrones.

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