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Williams’ film debut was in The Last Angry Man (1959), but he came to national attention in the television movie, Brian's Song (1971) which earned him an Emmy nomination for Best Actor. He has appeared in at least 70 films over six decades including critically acclaimed and popular movies such as, Lady Sings the Blues (1972) and Mahogany (1975) both starring Williams paired with Diana Ross; and Nighthawks (1981). In the 1980s he was cast in his most enduring role as Lando Calrissian, becoming the first African-American actor with a major role in the Star Wars franchise, in The Empire Strikes Back (1980), and Return of the Jedi (1983). He also delivered Lando as a voice actor in video games, animated series, and the National Public Radio adaptation of The Empire Strikes Back. He was inducted into the Black Filmmaker's Hall of Fame in 1984, and earned a star on the Hollywood Walk of Fame in 1985. Another enduring franchise relationship started with Batman (1989), playing attorney Harvey Dent, a role that was also developed into a villainous alter-ego, Two-Face, which he voiced for The Lego Batman Movie (2017).

Having broken through, Williams’ success with Brian's Song earned him a seven-year contract with Motown's Berry Gordy. He became one of America's most well-known black film actors of the 1970s, after starring in a string of critically acclaimed and popular movies, many of them in the "blaxploitation" genre. In 1972, he starred as Billie Holiday's husband Louis McKay in Motown Productions' Holiday biopic Lady Sings the Blues. The film was a box office blockbuster, becoming one of the highest-grossing films of the year and received five Academy Award nominations. Through his portrayal he became “a full-fledged sex symbol, touted as the ‘black Clark Gable.’” Diana Ross starred in Lady Sings the Blues opposite Williams; Motown paired the two of them again three years later in the successful follow-up project Mahogany.

He got permission from Star Wars’ creator George Lucas to sell lithographs of a montage of Williams’ iconic character from the franchise, Lando Calrissian. As of 2001 his paintings sold for an average of $10,000 to $35,000 (equivalent to $50,537 in 2019). "I call my paintings 'abstract reality.” Said Williams, “Sometimes I refer to them as 'impressions/expression.' It's the best way I can explain them." In early 2001 Williams was one of the celebrity artists painting seven-foot angel sculptures as part of the Oscar Academy’s sponsoring L.A.’s “A Community of Angels” charity project. The art angels were displayed for months then auctioned to raise funds for L.A. youth programs. In his online gallery biography, he states, “[an] interest in Eastern philosophy characterizes his images, first to record the physical reality, and then to uncover through the application of light, color and perspective. He cites Edward Hopper, M. C. Escher—the Dutch Master, Frida Kahlo, Tamara de Lempicka, Thomas Hart Benton, and the exciting, vibrant forms of African art as some of his strongest influences.” Williams’ work is included at the Schomburg Center for Research in Black Culture in New York, and the American Jazz Museum in Kansas City, Missouri.

In late 2019, Williams talked about his feminine side in an interview, and used masculine and feminine pronouns to refer to himself. Media outlets widely speculated that Williams might be gender fluid, but he clarified that he was referring to anima and animus: the feminine side of men and the masculine side of women in Jungian psychology.

Williams’ film debut was in The Last Angry Man (1959), but he came to national attention in the television movie Brian's Song, which earned him an Emmy Award nomination for Best Actor. He has appeared in at least 70 films over six decades, including critically acclaimed and popular movies Lady Sings the Blues (1972) and Mahogany (1975), which both starred Williams paired with Diana Ross, and Nighthawks (1981).

In 2014 Williams competed on the 18th season of Dancing with the Stars, a reality show/dancing competition partnered with professional dancer Emma Slater. The couple had to withdraw from the competition on the third week due to an injury to Williams's back.

He was commissioned for four paintings—including one of track and field star Jesse Owens sprinting, and another of a pair of boxers in a fight ring—for Nissan that were displayed at the 1996 Summer Olympics in Atlanta, Georgia. In 1997 he did paintings for Walt Disney Company’s Mighty Ducks arena for the Anaheim Ducks. From a description, circa late 1990s, at one of the galleries that carries his work, “Billy’s paintings are usually acrylic on canvas, applied with brush and airbrush. He also works with collage elements and has even created three-dimensional canvasses incorporating ceramic, Lucite, and neon light.”

In February 2011, Williams appeared as a guest star on USA Network's White Collar as Ford, an old friend of Neal Caffrey's landlady June, played by Diahann Carroll. In February 2012, Williams was the surprise guest during a taping of The Oprah Winfrey Show spotlighting Diana Ross. Ross and Williams were reunited after having not seen each other in 29 years. In October 2012, Williams appeared as a guest star on NCIS in Season 10 Episode 5 titled "Namesake", as Gibbs's namesake and his father's former best friend, Leroy Jethro Moore. On January 9, 2013, Williams made a cameo appearance as himself on Modern Family, season 4, episode 11 "New Year's Eve".

In 2008, Williams reprised his role as Lando Calrissian to appear in a video on Funny or Die in a mock political ad defending himself for leader of the Star Wars galaxy against vicious attack ads from Emperor Palpatine. Williams is currently a cast member of Diary of a Single Mom, a web-based original series directed by award-winning filmmaker Robert Townsend. The series debuted on PIC.tv in 2009.

Williams voiced Lando Calrissian in the video game Star Wars Jedi Knight II: Jedi Outcast and Star Wars Battlefront as well as the spin-off Star Wars Battlefront: Elite Squadron. However, the Battlefront appearances were archive footage and his voice-appearance in Elite Squadron is left uncredited or unknown. He also played a live-action character, GDI Director Redmond Boyle, in the game Command & Conquer 3: Tiberium Wars, which was released in March 2007. This made him the second former Star Wars actor to appear in a Command & Conquer game, with the first being James Earl Jones as GDI General James Solomon in Command & Conquer: Tiberian Sun. Williams voiced Lando Calrissian in 2015's Star Wars: Battlefront for the DLC pack Bespin and its 2017 sequel Star Wars Battlefront II. In the 2016 game Let It Die, Williams voices Colonel Jackson, who acts as the 2nd major boss players face.

In a 2001 interview he said, "Either I want to drop dead with a paint brush in my hand or I want to drop dead doing a soliloquy on the stage, I love acting. I love it. I take my acting very seriously, but I also find it fun. To do what children do and get paid for it is a lot of fun. I'm very fortunate." In late 2007 he was a guest artist on a ten-day Princess Cruise liner. They bought about eighty pieces which they put on their cruises and then auctioned off. He was commissioned for another set of Disney paintings to be unveiled in 2011 at Disney’s D23 Expo, also in Anaheim, California. For those, he set iconic Disney characters Mickey and Minnie Mouse, and Goofy in jazz music settings. In a 2011 interview he said, “I mostly create abstract paintings. I paint what's obvious to the eye and then incorporate an abstract point of view, which allows me a lot of space to play in. I work a lot with acrylic and oils, mostly acrylic right now and do a lot of line drawings.” In a September 2015 interview he said he finds painting “cathartic” compared to collective film work, “When you’re painting you just lock yourself up in your little private world. And it’s all about you and your imagination and nobody else interfering with that. It’s a great exercise because you really start discovering who you are and what you are without a lot of assistance … and the moment you come up with something interesting it’s a success that’s really based on your own personal, private sensibility.” As of 2019 he has made around 300 paintings, which Williams sees as his legacy.

Williams was arrested on January 30, 1996, after allegedly assaulting his live-in girlfriend, whom the police did not identify. He posted a US$50,000 bail. L.A. Police said the woman had minor bruises and scratches. The attorney's office filed misdemeanor charges of spousal battery and dissuading a witness. The woman later stated that the incident was her fault and hoped the police would drop the case. In a plea bargain, Williams agreed to undergo 52 counseling sessions. In a 2019 interview, Williams says he never slapped or abused women.

Williams made a special guest appearance on the hit sketch comedy show In Living Color in 1990. He portrayed Pastor Dan in an episode of That '70s Show. In this episode, "Baby Don't You Do It" (2004), his character is obsessed with Star Wars, and uses this to help counsel Eric Forman (himself a Star Wars fan) and Donna Pinciotti about his premarital relationship. Williams made a cameo appearance as himself on the television series Lost in the episode "Exposé". He also appears regularly on short clips on the Jimmy Kimmel Live! as a semi-parody of himself. In February 2006, Williams guest starred as himself in the season 5 episode "Her Story II" of Scrubs, where he plays the godfather of Julie (Mandy Moore). Turk hugs him, calling him "Lando", even though he prefers to be called Billy Dee. Williams played Toussaint Dubois for General Hospital: Night Shift in 2007 and 2008. Williams reprised his role as Toussaint on General Hospital beginning in June 2009. Also in 2009, Williams took on the role of the voice of Admiral Bitchface, the head of the military on the planet Titan, in the Adult Swim animated series Titan Maximum. In July 2010, Williams appeared in the animated series The Boondocks, where he voiced a fictionalized version of himself in the episode "The Story of Lando Freeman".

Williams is the Honorary Chairman of Thelonious Monk Institute of Jazz (TMIJ) in Washington, D.C., which fosters jazz education. TMIJ uses his artwork each year for its competition programs since 1990. He had his first solo exhibition in 1991 followed by many throughout North America, and later, the world. Around 1992, Williams, inspired by his friend and fellow New York artist Peter Max who had a teapot collection, started a cookie jar collection. Being an opera fan, he first found a jar in the shape of a singer in an opera gift shop by artisan couple Michael and Shelley Buonaiuto; later buying more than a dozen from their limited lines including ones of jazz artists Josephine Baker and Fats Waller. His 1993 self-portrait is at the National Portrait Gallery of the Smithsonian Institution (Washington D.C.) with a description that he “specializes in acrylic paintings combining traditional brushwork with an airbrushing technique;” he also works in oils. Williams painted a series of impressionistic portraits of the Tuskegee Airmen, the “African-American pilots whose real-life exploits changed the course of American military history.” He started the series in the 1990s but when officials from National Air and Space Museum (NASM) saw them they wanted more, and to use them in an exhibition. In 1999 they were displayed at the African-American Museum of Art, Culture and History in New Orleans, and in early-2000, the NASM in Washington, D.C.

Thirty years later, in the early 1990s, he sang on a “celebrity-packed charity single,” “Voices That Care,” to honor U.S. troop of Operation Desert Storm, the 1990-1991 Gulf War, and supporting the International Red Cross. The single reached number eleven on the Billboard Hot 100, and number six on the Hot Adult Contemporary Tracks. Through sales and plays of the song Williams and the other celebrities became platinum-recording and Billboard-charting artists.

Williams co-starred in 1989's Batman as district attorney Harvey Dent, a role that was planned to develop into Dent's alter-ego, the villain Two-Face, in sequels. However, that never came to pass; he was set to reprise the role in the sequel Batman Returns, but his character was deleted and replaced with villain Max Shreck. When Joel Schumacher stepped in to direct Batman Forever, where Two-Face was to be a secondary villain, Schumacher decided to hire Tommy Lee Jones for the role. There was a rumor that Schumacher had to pay Williams a fee in order to hire Jones, but Williams said that it was not true: "You only get paid if you do the movie. I had a two-picture deal with Star Wars. They paid me for that, but I only had a one picture deal for Batman." Williams eventually voiced Two-Face in the 2017 film The Lego Batman Movie.

In the 1984–1985 season of Dynasty, he played Brady Lloyd opposite Diahann Carroll. Williams was paired with actress Marla Gibbs on three situation comedies: The Jeffersons (Gibbs's character, Florence, was in love with Williams and challenged him on everything because she thought Williams was an imposter); 227 (her character, Mary, pretending to be royalty, met Williams at a banquet); and The Hughleys (Gibbs and Williams portrayed Darryl's parents). In 1992, he portrayed Berry Gordy in The Jacksons: An American Dream. In 1993, Williams made a guest appearance on the spin-off to The Cosby Show, A Different World, as Langston Paige, a grumpy landlord, in a backdoor pilot for his own series. Williams appeared as himself on Martin where he provided Martin Lawrence's character with advice on getting back together with Gina.

Williams was cast as Lando Calrissian in The Empire Strikes Back (1980), becoming the first African-American actor with a major role in the series. J. J. Abrams, who would direct Williams in the ninth installment film in 2019, noted, “Lando was always written as a complex, contradictory, nuanced character. And Billy Dee played him to suave perfection, ... It wasn’t just that people of color were seeing themselves represented; they were seeing themselves represented in a rich, wonderful, intriguing way.” He would reprise the role soon after in Return of the Jedi (1983). Between the latter two films, he starred alongside Sylvester Stallone as a cop in the thriller Nighthawks (1981). The charm of his role as Lando Calrissian proved to be popular with audiences. Williams has voiced the character in the 2002 video game Jedi Knight II: Jedi Outcast, the audio dramatization of Dark Empire, the National Public Radio adaptation of The Empire Strikes Back, two productions for the Star Wars: Battlefront series, The Lego Movie, and in two episodes of the animated TV series Star Wars Rebels. Some fans were disappointed with Calrissian's absence from the first film in the Star Wars sequel trilogy, The Force Awakens, but in July 2018 it was announced that he would reprise his role in The Rise of Skywalker (2019), marking one of the longest intervals between onscreen portrayals of a character by the same actor in American film history.

Williams' television work included a recurring guest-starring role on the short-lived show Gideon's Crossing. He is also known for his advertisements for Colt 45, a malt liquor, for a five-year period starting in the mid-1980s; he would reprise his spokesperson role in 2016. Williams brushed off criticism—for the subtext of the ad campaign, ‘works every time,’ and the target audience—of the choice, "I drink, you drink. Hell, if marijuana was legal, I'd appear in a commercial for it." Colt 45 hired Williams “simply because he was so cool,” and went from trailing behind Joseph Schlitz Brewing Company in barrels produced, to “skyrocketing” a year after the 1986 ads ran to two million barrels in the top spot for malt liquor.

In the late 1980s, Williams resumed painting devoting much of his time to the work. He returned to New York to star in August Wilson’s play Fences replacing James Earl Jones in the lead for four months starting in February 1988. It marked a turning point for him, returning home, and for him, the center of the art scene. He also renewed his friendship with Peter Max who had also trained, and sold art in the city, and renewed Williams' interest in painting. Within a two year span he “cranked out 120 original works of art.”

In the 1980s he was cast as Lando Calrissian in The Empire Strikes Back (1980) and Return of the Jedi (1983). He would portray Lando in the Star Wars franchise for nearly forty years, including The Rise of Skywalker (2019), and as a voice actor in video games and animated series. Another enduring franchise relationship started with Batman (1989) playing attorney Harvey Dent, a role that was also developed into a villainous alter-ego, Two-Face, which he voiced for The Lego Batman Movie (2017).

He married Teruko Nakagami on December 27, 1972. She brought a daughter, Miyako (b. 1962), from her previous marriage to musician Wayne Shorter. Together they have a daughter, Hanako (b. 1973). In 1984 he bought a “Zen-like contemporary” home in the Trousdale Estates neighborhood of Beverly Hills, California; he sold it in 2012. He filed for an amicable divorce from Nakagami in 1993, but they reconciled, and were again living together by 1997.

He rose to stardom after starring in the critically lauded blockbuster biographical television movie, Brian's Song (1971), in which he played Chicago Bears star football player Gale Sayers, who stood by his friend Brian Piccolo (played by James Caan), during Piccolo's struggle with terminal cancer. The film was so popular that it was given a theatrical release. Both Williams and Caan were nominated for Emmy Awards for best actor for their performances. Williams said the role was the one of which he was most proud:

Williams's television work has over sixty credits starting in 1966 including recurring roles over the decades in Gideon's Crossing; Dynasty, General Hospital: Night Shift; and General Hospital. Numerous cameos and supporting roles included being paired with Marla Gibbs on The Jeffersons, 227, and The Hughleys. Later work included voice acting in the series Titan Maximum (2009), and appearing on the reality show Dancing with the Stars (2014). His work has earned him numerous awards and honors including three NAACP Image Awards, and the NAACP Lifetime Achievement award.

The album included the first-ever vocal recording of “A Taste of Honey”, a song by Bobby Scott and Ric Marlow later covered by The Beatles on their 1963 debut album Please Please Me. Williams was the first to sing the song in the U.S., on the Broadway stage with Joan Plowright as part of the original Broadway production of the play A Taste of Honey. Williams said of the album, “Recording it was sort of a lark. I did some singing in clubs, for a moment, and then I stopped. I have too much respect for singers to really think that I'm a singer.” The album was re-released on CD, Download and Streaming platforms in 2014 and continues to be available.

In 1961, Williams recorded a jazz LP produced by Prestige Records entitled Let's Misbehave, on which he sang swing standards. The album, which was a commercial success, earned Williams a spot on Motown 25: Yesterday, Today, Forever (1983).

Williams made his film debut in 1959 in The Last Angry Man, opposite Paul Muni, in which he portrayed a delinquent young man. He was frustrated in the 1960s with the “paucity of parts for leading black men,” the majority of roles he wanted went to Sidney Poitier. He enjoyed doing theater and television, but “his slow-building film career ate at him.” He found LSD, a popular hallucinogenic drug with the era’s hippie movement to be a cure, “LSD saved my life ... I wasn’t doing it to get high. It let me get inside of myself.” Otherwise he is anti-drug.

Williams has been married three times, and has three children, and two grandchildren. His first marriage was to Audrey Sellers in 1959. They were divorced some years later, after which he apparently became depressed. He stated that "there was a period when I was very despondent, broke, depressed, my first marriage was on the rocks." They had a son, Corey Dee Williams, born in 1960. In 1968, Williams married model and actress Marlene Clark in Hawaii. They divorced in 1971. He moved from New York City to California in 1971.

Williams attended Booker T. Washington Junior High School where he had dreams of being a painter. He graduated in 1955 from the LaGuardia High School of Music & Art and Performing Arts in Manhattan, where he majored in arts with a focus on visual arts. The school would later be the subject for Fame (1980), and its derivative television series. While there he got a two-year scholarship for the National Academy of Fine Arts and Design in New York—which later changed its name to National Academy of Design—to study with a focus on "classical principles of painting". He was nominated at eighteen or nineteen years old for a Guggenheim Fellowship grant—for “creative ability in the arts;” and won a Hallgarten Prize in the mid-1950s. Although he had scholarships to pay for school tuition, he turned to acting to pay for his paints, supplies, and canvasses. His first Broadway theatre “big break” was a play, A Taste of Honey. He continued to struggle as an actor for ten years working as an extra, doing small and large theatre, and “slowly breaking into television and film”. During art school he gained interest in the Stanislavsky Method—experiencing a role contrasted with representing it, to mobilize an actor's conscious thought and will to in turn activate emotional response and subconscious behavior—and began studying at the Harlem Actors Workshop. It was run by blacklisted actor Paul Mann who embraced actors of all races; Williams also studied there under Sidney Poitier. He first viewed his acting as a way to pay for his art supplies, by the early 1960s though he began to “devote all of his energy to performance.” In succession he got an actor agent through a friend, started getting major Off-Broadway roles, then work on Broadway.

Williams was born in New York City, and raised with his twin sister Loretta in Harlem. In 1945 he made his Broadway theatre debut at age seven in The Firebrand of Florence. He later graduated from The High School of Music & Art, then won a painting scholarship to the National Academy of Fine Arts and Design, where he won a Hallgarten Prize for painting in the mid-1950s. To fund his art supplies he returned to acting, including stage, films, and television. He continued painting; his work has since been shown in galleries and collections worldwide.

Williams first appeared on Broadway in 1945 in The Firebrand of Florence. He returned to Broadway as an adult in 1960 in the adaptation of The Cool Word. He appeared in A Taste of Honey in 1960. A 1976 Broadway production, I Have a Dream, was directed by Robert Greenwald and starred Williams as Martin Luther King Jr. His most recent Broadway appearance was in August Wilson's Fences, as a replacement for James Earl Jones in the role of Troy Maxson in 1988.

William December "Billy Dee" Williams Jr. (born April 6, 1937) is an American actor, voice actor, and artist. He is best known as Lando Calrissian in the Star Wars franchise, first in the early 1980s, and nearly forty years later in The Rise of Skywalker (2019), marking one of the longest intervals between onscreen portrayals of a character by the same actor in American film history.

William December Williams Jr. was born in New York City, the son of Loretta Anne (1915–2016), a West Indian-born elevator operator at the Lyceum Theatre and aspiring performer from Montserrat, and William December Williams, Sr. (1910–2008), an African-American caretaker, with some Native American ancestry from Texas. He grew up in Harlem on 110th Street, between Lenox and 5th, adjacent to Central Park North–110th Street station. He used to go to Central Park to see the Negro league players and the Cuban baseball league, “They were fantastic, and I wound up working with a lot of those guys,” (in The Bingo Long Traveling All-Stars & Motor Kings (1976)). He has a twin sister, Loretta, and they were raised by their maternal grandmother while their parents worked several jobs. His mom had studied opera for years, becoming an accomplished opera star who wanted to break into movies; the family was richly cultured, exposing the children early on to drawing, painting, theatre and similar creative experiences; Billy Dee would remain a fan of the arts including opera. In March 1945 he made his Broadway debut at age seven portraying a page in The Firebrand of Florence, Kurt Weill and Ira Gershwin’s operetta starring Lotte Lenya. His mom, who worked at the theatre, volunteered him for the part which he found boring.