Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film ‘Star Wars: The Rise of Skywalker’, in central London in December 2019.
Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film 'Star Wars: The Rise of Skywalker', in central London in December 2019. Williams, who has written a new memoir, will be in Chicago this week for a WBEZ event. Vianney Le Caer/Invision/AP
Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film ‘Star Wars: The Rise of Skywalker’, in central London in December 2019.
Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film 'Star Wars: The Rise of Skywalker', in central London in December 2019. Williams, who has written a new memoir, will be in Chicago this week for a WBEZ event. Vianney Le Caer/Invision/AP

With both swagger and a swoosh of his powder blue cape, he made history. Billy Dee Williams, the first Black actor to enter the Star Wars universe, caught the attention of audiences everywhere with just four words: “What have we here?”

Those are the iconic words of Lando Calrissian in Star Wars Episode V: The Empire Strikes Back, and they also make up the title of Williams’ new memoir. In What Have We Here: Portraits Of A Life, the actor tells stories from his decades-long career, the moments and opportunities he says changed the trajectory of his life and the legacy he hopes to leave behind.

Ahead of his stop in Chicago for “WBEZ Presents: An Evening with Billy Dee Williams” this Thursday, Williams sat down with Reset to discuss his memoir, how he created the persona of his Star Wars character and how he has always seen himself as a romantic lead. Here are some highlights from the conversation, which was edited and condensed for publication. Press the red play button above to hear the full interview.

Reset: I want to start with something that you mentioned toward the end of your book. This is a recurring dream that you said that you’ve been having lately, where you’re saying goodbye to friends, you’re walking to your car, but you can’t find the car and that’s got you lost and confused. What do you think it means?

Williams: I haven’t figured it out yet, but I do have that recurring dream. It’s been going on for a number of years now. I don’t, I don’t understand it. I don’t know. I haven’t figured it out yet.

Williams spoke to WBEZ's Reset about his new memoir.
Williams spoke to WBEZ’s Reset about his new memoir.

You said [in your book] it has you unsettled and thinking about your legacy. Is that maybe something that led you down the path of writing a memoir?

Well, you know, I’m at that age now. I think you start thinking in terms of legacy, you know, what do I say about my life? One thing, you know, when we’re questioning our lives, we get so mad — these days in particular […] it’s either black or it’s white. But my life has been a very eclectic kind of life and always sort of incorporates everything and everybody. I mean, I see myself as the full spectrum of colors and to me that gives me a real sense of creativity and it makes life a lot more fun rather than choosing one thing or the other.

I think that in writing the story of our lives, other people might find themselves in a somber space and reliving struggles and traumas. But with you, we’re getting how much fun you had on this journey. Is that right? Has it been more laughs than tears?

Yeah, I would say so. You know, I think of myself as a walking absurdity, which is a good place to start. There’s no period in my life. It continues to go on and on and on and on.

In your book you said your approach to life has always been more of an “artful improvisation.” What do you mean exactly?

Unplanned. If I say I want to go right, something tells me no, no, no, no, no, no, no, no, go left. It’s going with instincts, allowing myself to go with my instinct. So it becomes a wonderful improvisational exercise.

I think some folks would be surprised to learn that painting was another love of yours, and it’s what you went to school for.

My sister and I — my twin sister, Lady — were very, very good artists in school. We went to [LaGuardia High School of Music & Art] in New York. And then she went off to NYU and I got a scholarship to a school, the National Academy of Fine Arts and Design. I spent two years there painting. I was nominated for Guggenheim [Fellowship Grant]. But so the world of creativity has always been my life. I don’t really know any other life.

Do you think that you might still make a book dedicated to your paintings? Do we have a Billy Dee Williams coffee table picture book in our future?

Yes, I’ve been working on it for about 20 years or more. That’s the next thing I’m going to do — or finish anyway. It’s telling my life through my paintings. And, yeah, it will be amazing, actually. Stored away, I have over 300 paintings. So I have a lot to draw from.

You have played more than 100 movie and TV roles in your career. But we do have to talk about one that really stands out: Lando Calrissian. Now when JJ Abrams asked if you were ready to take the cape up again for the film Rise of the Skywalker at the time, you said “JJ, I’ve never not been Lando.” So do you think that that’s why the character has been such a pop culture icon — because Lando is really you?

Yeah, well I kind of developed that whole character the moment I heard his name Calrissian. I said, Calrissian is an Armenian name and I said, my goodness, let me see what I can do with that. And then of course, when I got the cape, that kind of solidified the whole adventure in creating this character. I wanted to make him bigger than life. I wanted him to be more than just a Black character, but I wanted to take it further and make it much more interesting.

My personal favorite [film] of yours has got to be Lady Sings The Blues. This tells the story of singer Billie Holiday’s life, and it had you co-starring with Diana Ross. In the book, you actually write, “I saw enormous potential in this project, obviously for Diana, but also for me to present a Black man in a way that I hadn’t ever seen in the movies.” Was that a lot of pressure?

No, there’s no pressure. No, I always saw myself playing a romantic lead character and I love romance. But the kind of movies I used to love back in those years were sophisticated comedies with people like Myrna Loy and Melvyn Douglas and William Powell, and I love that kind of stuff. And so I always saw myself as a romantic lead and I accomplished that in a way that no little brown-skinned boy had ever accomplished.”

One hundred-plus roles later, do you think there are any that escaped you? Is there any role that you still would love to play?

Well, I always wanted to do Duke Ellington’s life. I thought I was the only one that could really pull it off because I understand that sensibility, but it never happened.

There’s still time.

We’ll see. Who knows. I met him a couple of times in my life. And he was quite intriguing, very charming and that kind of charm I don’t see with a lot of the young men today.

If you go: WBEZ Presents: An Evening with Billy Dee Williams takes place at 7 p.m. on Thursday, Feb. 22 at Francis Parker School, 330 W. Webster Ave. Tickets start at $27.50.

Meha Ahmad is the senior producer of WBEZ’s Reset. Sasha-Ann Simons is the host of WBEZ’s Reset.

Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film ‘Star Wars: The Rise of Skywalker’, in central London in December 2019.
Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film 'Star Wars: The Rise of Skywalker', in central London in December 2019. Williams, who has written a new memoir, will be in Chicago this week for a WBEZ event. Vianney Le Caer/Invision/AP
Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film ‘Star Wars: The Rise of Skywalker’, in central London in December 2019.
Actor Billy Dee Williams poses for photographers upon arrival at the premiere for the film 'Star Wars: The Rise of Skywalker', in central London in December 2019. Williams, who has written a new memoir, will be in Chicago this week for a WBEZ event. Vianney Le Caer/Invision/AP

With both swagger and a swoosh of his powder blue cape, he made history. Billy Dee Williams, the first Black actor to enter the Star Wars universe, caught the attention of audiences everywhere with just four words: “What have we here?”

Those are the iconic words of Lando Calrissian in Star Wars Episode V: The Empire Strikes Back, and they also make up the title of Williams’ new memoir. In What Have We Here: Portraits Of A Life, the actor tells stories from his decades-long career, the moments and opportunities he says changed the trajectory of his life and the legacy he hopes to leave behind.

Ahead of his stop in Chicago for “WBEZ Presents: An Evening with Billy Dee Williams” this Thursday, Williams sat down with Reset to discuss his memoir, how he created the persona of his Star Wars character and how he has always seen himself as a romantic lead. Here are some highlights from the conversation, which was edited and condensed for publication. Press the red play button above to hear the full interview.

Reset: I want to start with something that you mentioned toward the end of your book. This is a recurring dream that you said that you’ve been having lately, where you’re saying goodbye to friends, you’re walking to your car, but you can’t find the car and that’s got you lost and confused. What do you think it means?

Williams: I haven’t figured it out yet, but I do have that recurring dream. It’s been going on for a number of years now. I don’t, I don’t understand it. I don’t know. I haven’t figured it out yet.

Williams spoke to WBEZ's Reset about his new memoir.
Williams spoke to WBEZ’s Reset about his new memoir.

You said [in your book] it has you unsettled and thinking about your legacy. Is that maybe something that led you down the path of writing a memoir?

Well, you know, I’m at that age now. I think you start thinking in terms of legacy, you know, what do I say about my life? One thing, you know, when we’re questioning our lives, we get so mad — these days in particular […] it’s either black or it’s white. But my life has been a very eclectic kind of life and always sort of incorporates everything and everybody. I mean, I see myself as the full spectrum of colors and to me that gives me a real sense of creativity and it makes life a lot more fun rather than choosing one thing or the other.

I think that in writing the story of our lives, other people might find themselves in a somber space and reliving struggles and traumas. But with you, we’re getting how much fun you had on this journey. Is that right? Has it been more laughs than tears?

Yeah, I would say so. You know, I think of myself as a walking absurdity, which is a good place to start. There’s no period in my life. It continues to go on and on and on and on.

In your book you said your approach to life has always been more of an “artful improvisation.” What do you mean exactly?

Unplanned. If I say I want to go right, something tells me no, no, no, no, no, no, no, no, go left. It’s going with instincts, allowing myself to go with my instinct. So it becomes a wonderful improvisational exercise.

I think some folks would be surprised to learn that painting was another love of yours, and it’s what you went to school for.

My sister and I — my twin sister, Lady — were very, very good artists in school. We went to [LaGuardia High School of Music & Art] in New York. And then she went off to NYU and I got a scholarship to a school, the National Academy of Fine Arts and Design. I spent two years there painting. I was nominated for Guggenheim [Fellowship Grant]. But so the world of creativity has always been my life. I don’t really know any other life.

Do you think that you might still make a book dedicated to your paintings? Do we have a Billy Dee Williams coffee table picture book in our future?

Yes, I’ve been working on it for about 20 years or more. That’s the next thing I’m going to do — or finish anyway. It’s telling my life through my paintings. And, yeah, it will be amazing, actually. Stored away, I have over 300 paintings. So I have a lot to draw from.

You have played more than 100 movie and TV roles in your career. But we do have to talk about one that really stands out: Lando Calrissian. Now when JJ Abrams asked if you were ready to take the cape up again for the film Rise of the Skywalker at the time, you said “JJ, I’ve never not been Lando.” So do you think that that’s why the character has been such a pop culture icon — because Lando is really you?

Yeah, well I kind of developed that whole character the moment I heard his name Calrissian. I said, Calrissian is an Armenian name and I said, my goodness, let me see what I can do with that. And then of course, when I got the cape, that kind of solidified the whole adventure in creating this character. I wanted to make him bigger than life. I wanted him to be more than just a Black character, but I wanted to take it further and make it much more interesting.

My personal favorite [film] of yours has got to be Lady Sings The Blues. This tells the story of singer Billie Holiday’s life, and it had you co-starring with Diana Ross. In the book, you actually write, “I saw enormous potential in this project, obviously for Diana, but also for me to present a Black man in a way that I hadn’t ever seen in the movies.” Was that a lot of pressure?

No, there’s no pressure. No, I always saw myself playing a romantic lead character and I love romance. But the kind of movies I used to love back in those years were sophisticated comedies with people like Myrna Loy and Melvyn Douglas and William Powell, and I love that kind of stuff. And so I always saw myself as a romantic lead and I accomplished that in a way that no little brown-skinned boy had ever accomplished.”

One hundred-plus roles later, do you think there are any that escaped you? Is there any role that you still would love to play?

Well, I always wanted to do Duke Ellington’s life. I thought I was the only one that could really pull it off because I understand that sensibility, but it never happened.

There’s still time.

We’ll see. Who knows. I met him a couple of times in my life. And he was quite intriguing, very charming and that kind of charm I don’t see with a lot of the young men today.

If you go: WBEZ Presents: An Evening with Billy Dee Williams takes place at 7 p.m. on Thursday, Feb. 22 at Francis Parker School, 330 W. Webster Ave. Tickets start at $27.50.

Meha Ahmad is the senior producer of WBEZ’s Reset. Sasha-Ann Simons is the host of WBEZ’s Reset.