Billy Dee Williams

• 1. Introduction

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  Billy Dee Williams was born William December Williams Jr. on the 6th of April 1937, in New York City, and by the time he was seven years old, he had already taken his first bow on a Broadway stage. That debut, in Kurt Weill and Ira Gershwin's operetta The Firebrand of Florence in March 1945, came not because he craved the spotlight but because his mother, a Lyceum Theatre elevator operator who dreamed of movies, volunteered him for the part. He found it boring. That small, reluctant debut is a clue to everything that followed: a life in which acting kept interrupting something else Billy Dee actually loved. He grew up wanting to be a painter. He studied at the National Academy of Fine Arts and Design on a scholarship and won a Hallgarten Prize for his canvasses in the mid-1950s. He turned to acting only because he needed money for paints and supplies. What happened next, over more than six decades and over 100 film and television roles, is the story of a man who kept trying to paint and kept becoming famous instead. He became the first African-American actor with a major role in the Star Wars franchise. He was called the black Clark Gable by a national newspaper. He earned three NAACP Image Awards, a star on the Hollywood Walk of Fame, and eventually returned to painting with such devotion that by 2019 he had made around 300 works he considers his real legacy. The question the rest of this documentary will answer is how those two lives, the painter and the star, actually fit together.

• 2. Harlem to Broadway

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  Williams grew up on 110th Street in Harlem, between Lenox and 5th Avenue, adjacent to the Central Park North station, a neighborhood where culture was woven into the household. His mother, Loretta Anne, had studied opera for years and became an accomplished singer who wanted to break into movies. His father, William December Williams Sr., was an African-American caretaker with some Native American ancestry from Texas. The children, including Williams's twin sister, Loretta, were raised by their maternal grandmother while their parents worked multiple jobs. Williams would later recall heading to Central Park to watch Negro league and Cuban baseball players. He described them as fantastic, and he would eventually work alongside some of those same men in The Bingo Long Traveling All-Stars and Motor Kings in 1976.

  At Booker T. Washington Junior High School, his primary ambition was painting. He graduated in 1955 from the LaGuardia High School of Music and Art and Performing Arts in Manhattan, majoring in visual arts. That school would later inspire the 1980 film Fame and its television spin-off. He won a two-year scholarship to the National Academy of Fine Arts and Design in New York, where his studies centered on classical principles of painting. At roughly eighteen or nineteen, he was nominated for a Guggenheim Fellowship. He won a Hallgarten Prize in the mid-1950s for his painterly ability. But scholarships covered tuition, not brushes and canvas, so he turned to acting.

  He trained at the Harlem Actors Workshop, run by blacklisted actor Paul Mann, who welcomed performers of all races. Williams studied there alongside Sidney Poitier. He explored the Stanislavsky Method, which treats acting as an activation of genuine emotional and subconscious response rather than a simulation of it. His first Broadway big break as an adult was in A Taste of Honey in 1960. By the early 1960s, after a decade of extra work and small roles, he had shifted from treating acting as a means to an end and began devoting all of his energy to performance.

• 3. Brian's Song and the Motown Years

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  Brian's Song, the 1971 television film, changed everything. Williams played Gale Sayers, the Chicago Bears star who stayed loyal to his terminally ill teammate Brian Piccolo, played by James Caan. Both actors were nominated for Primetime Emmy Awards for best actor. Williams later called it the role of which he was most proud. His own description of it as a love story between two men, without sex, and a breakthrough in terms of racial division, captures why the film hit so hard at the time.

  The attention earned him a seven-year contract with Berry Gordy's Motown Productions. In 1972, he starred opposite Diana Ross in Lady Sings the Blues, the Academy Award-nominated biopic of Billie Holiday, playing her husband Louis McKay. A national newspaper dubbed him the black Clark Gable. Williams was blunt about what that comparison meant to him. He wanted to be known as one of the best actors of his generation, full stop. The opportunities, he said, were not the same for him as they had been for Gable, and he was frustrated.

  Motown paired him with Ross again in Mahogany in 1975. Two years later he played the title role in Scott Joplin, the musician's biopic, which featured ragtime pieces throughout and opened with what the source describes as an epic piano duel. In 1976, he appeared in the ensemble baseball comedy The Bingo Long Traveling All-Stars and Motor Kings. In 1978, he returned to Broadway in I Have a Dream, playing Martin Luther King Jr. in a production directed by Robert Greenwald. These years built his reputation as one of the most prominent black film actors in America.

• 4. Lando Calrissian

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  In 1980, Star Wars: The Empire Strikes Back gave Williams a role that no amount of television work or blaxploitation stardom could have predicted. Cast as Lando Calrissian, the smooth-talking administrator of Cloud City, he became the first African-American actor with a major role in the Star Wars franchise. He reprised the role in Return of the Jedi in 1983, and also voiced Lando in the audio drama adaptation of The Empire Strikes Back that same year.

  The role carried cultural weight that Williams understood precisely. Director J.J. Abrams, when Williams returned for Star Wars: The Rise of Skywalker in 2019, put it plainly: people of color were seeing themselves represented in a rich, wonderful, intriguing way. Lando, Abrams noted, was always written as a complex, contradictory, nuanced character, and Williams played him to suave perfection. The gap between 1983 and 2019 made that return one of the longest intervals between an actor's onscreen portrayals of the same character in American film history.

  The Lando role also came with legal complications. Williams had co-starred in the 1989 film Batman as district attorney Harvey Dent, with a two-picture deal intended to develop the character into villain Two-Face. His character was cut from Batman Returns. When Joel Schumacher took over to direct Batman Forever and cast Tommy Lee Jones as Two-Face, a rumor spread that Schumacher had paid Williams a fee to hire Jones. Williams denied it, noting that his deal had been a one-picture arrangement for Batman, distinct from his two-picture Star Wars contract. He eventually voiced Two-Face in The Lego Batman Movie in 2017, closing that particular loop.

• 5. A Painter in Parallel

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  In the late 1980s, a stage role pulled Williams back to New York and back to painting. He replaced James Earl Jones in the lead of August Wilson's Fences for four months starting in February 1988, taking on the role of Troy Maxson on Broadway. Being back in New York reconnected him with his friend Peter Max, a fellow New York artist who had also trained and sold work in the city. Within a two-year span, Williams produced 120 original works.

  He had his first solo exhibition in 1991. His 1993 self-portrait entered the collection of the National Portrait Gallery of the Smithsonian Institution in Washington, D.C. The institution's description identifies his technique as acrylic paintings combining traditional brushwork with airbrushing; he also worked in oils. The Herbie Hancock Institute of Jazz in Washington, D.C., where Williams serves as honorary chairman, has used his artwork for its competition programs every year since 1990.

  He painted a series of impressionistic portraits of the Tuskegee Airmen, the African-American pilots whose exploits reshaped American military history. When officials from the National Air and Space Museum saw them they requested more for an exhibition. In 1999 the series appeared at the African-American Museum of Art, Culture and History in New Orleans, and in early 2000 at the NASM itself in Washington, D.C. For the 1996 Summer Olympics in Atlanta, he was commissioned to produce four paintings for Nissan, including one of Jesse Owens sprinting and another of boxers in a ring. In 1997, he made paintings for the Anaheim Ducks arena at the Walt Disney Company's Mighty Ducks facility.

  Williams described his work as abstract reality, sometimes impressions and expression, and cited Edward Hopper, M.C. Escher, Frida Kahlo, Tamara de Lempicka, Thomas Hart Benton, and African art as his strongest influences. As of 2001, his paintings were selling for between ten thousand and thirty-five thousand dollars each. In a 2015 interview he called painting cathartic: a private world where no one else interferes, and where success comes from personal, private sensibility. By 2019, the roughly 300 paintings he had completed were what he considered his true legacy.

• 6. Music and the Written Word

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  In 1961, Williams recorded a jazz LP for Prestige Records called Let's Misbehave, named after its second track. The album included the first-ever vocal recording of the song A Taste of Honey, written by Bobby Scott and Ric Marlow. The Beatles would later cover that song on their 1963 debut album Please Please Me. Williams was also the first to sing the song in the United States, on the Broadway stage opposite Joan Plowright in the original Broadway production of the play it shares its name with. Williams was modest about his vocal abilities. He described recording the album as a lark, adding that he had too much respect for singers to actually consider himself one. The album was re-released on CD, download, and streaming platforms in 2014.

  In the early 1990s, Williams lent his voice to a celebrity charity single called Voices That Care, recorded to honor U.S. troops serving in Operation Desert Storm during the 1990-1991 Gulf War, with proceeds supporting the International Red Cross. The single reached number eleven on the Billboard Hot 100 and number six on the Hot Adult Contemporary Tracks. Williams and the other participants became platinum-recording artists as a result.

  His work extended into fiction and comics. He co-wrote the novel PSI/Net in 1999 with Rob MacGregor, a thriller based on a real government program of psychic spying. A follow-up novel, JUST/In Time, appeared in 2001. In 2021 and 2022, DC Comics published Batman '89, a comic book using Williams's likeness to depict Harvey Dent's transformation into Two-Face, the arc that the 1989 film had originally promised and never delivered.

• 7. A Life Beyond the Screen

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  Williams's television footprint stretches across more than 70 credits dating back to 1966. In the 1984-1985 season of Dynasty, he played Brady Lloyd opposite Diahann Carroll. He appeared in three situation comedies alongside actress Marla Gibbs: The Jeffersons, 227, and The Hughleys. In 1992, he played Berry Gordy himself in The Jacksons: An American Dream. His Colt 45 malt liquor advertisements, which ran for five years starting in the mid-1980s, became a cultural touchstone. He reprised the spokesperson role in 2016. The year after the ads launched in 1986, Colt 45 moved from trailing Joseph Schlitz Brewing Company to producing two million barrels and reaching the top spot in malt liquor.

  His personal life was marked by three marriages. He married Audrey Sellers in 1959; they had a son, Corey Dee Williams, born in 1960, before divorcing. He married model and actress Marlene Clark in Hawaii in 1968, and they divorced in 1971. On the 27th of December 1972, he married Teruko Nakagami, who brought a daughter, Miyako, born in 1962, from her previous marriage to musician Wayne Shorter. Williams and Nakagami had a daughter, Hanako, born in 1973. He filed for divorce from Nakagami in 1993, but they reconciled and were living together again by 1997.

  In 2019, Williams spoke publicly about his feminine side and used masculine and feminine pronouns in reference to himself. When media outlets described him as gender fluid, he clarified that he was drawing on Jungian psychology, specifically the concept of anima and animus: the feminine side present in men and the masculine side present in women.

  He was inducted into the Black Filmmaker's Hall of Fame in 1984, and in 1985 he received a star on the Hollywood Walk of Fame at 1521 Vine Street. Of his decades of fan interactions, particularly at science fiction conventions, Williams has said they have been mostly positive, and that he expects to have an audience for the rest of his life.