In His New Memoir, Billy Dee Williams Recalls Posing Nude, a Failed Proposal and a Dirty Joke with Big Backlash

'I've led a crazy life,' the 86-year-old actor tells PEOPLE in this week's issue ahead of the release of his new memoir 'What Have We Here?'

Billy Dee Williams is grateful for how his life has turned out.

“I’m always chuckling about myself. I think much of my life is dictated by chance and happenstance,” the 86-year-old actor tells PEOPLE in this week’s issue while discussing his new memoir, What Have We Here? Portraits of a Life, available now from Penguin Random House.

A lifetime of navigating relationships, career moves, racial injustice and, of course, playing Lando Calrissian in the Star Wars franchise, leaves a person with a crop stories and lessons to share. “I’ve led a crazy life," Williams says. "At this stage I’m thinking about legacy, so I figured I need to talk about a few things that might interest a few people.”

From failed proposals to nude modeling and recurring dreams about mortality, here are the biggest bombshells from the actor’s new tell-all memoir, What Have We Here?

Related: Billy Dee Williams Gets Candid About Infidelity: ‘I’ve Been Philandering My Whole Life’ (Exclusive) 

Williams Once Worked as a Nude Model for Art Students

In What Have We Here?, the actor writes that he always planned on being an artist, but the art form changed over the years. During his second year at the National Academy of Design, Williams took a class called Life Study, in which he would frequently draw the nude models standing in front of him.

“When a model removed their clothes, they weren’t just exposing their bodies. They were revealing their vulnerability and humanity,” he writes.

For a few months, Williams tried his hand at nude modeling himself for the Art Students League and Parsons School of Design, but quickly discovered it was tougher than it looked.

“I made six dollars per class, pretty good money then. But holding the same pose for two to three hours was more than I could bear,” he writes. “My entire body ached and cried out to change positions, to get up and do something else. Holding something still like that was unnatural.”

As An Actor, He Had to Prove He Could Do the Job

While starring in The Last Angry Man, Williams found both friendship and guidance in his co-star Paul Muni.

Williams says it was his father’s influence — and then Muni’s — that made him a pragmatist. “I saw how essential it was to do the work,” he writes. “You couldn’t sit around and dream about being a success. You had to put in the hours to make it happen and then prove you could do the job.”

He writes, “When I acted, I wanted people to see the character I was trying to portray, not me, a skinny Black young man from Harlem.”

His High School Girlfriend Turned Down His Marriage Proposal

Williams’ rising fame and the “money in [his] bank account” led him to believe that it was time to propose to his high school sweetheart, Sondra.

“Like so many things in my life, the decision was based partly on instinct and partly on insanity," he writes. "I didn’t think it through…I simply felt like this was the next important step in growing up, and I was ready.”

The actor had just finished The Last Angry Man, his first major Hollywood motion picture, and Sondra was back from Spelman College; “The timing seemed right.” He placed the diamond engagement ring on the dinner table in front of her and asked for her hand in marriage.

“The look of surprise that appeared on her face let me know that she didn't expect a proposal,” Williams writes. “She inspected the ring without removing it from the box, as if trying it on was the last thing she wanted to do. Then she delivered her own surprise,”

She had met someone “special” while at Spelman. “Sondra then told me that she was in love not with another man she’d met at school, but with a woman. Now it was my turn to be surprised for obvious reasons,” he writes. “I loved her and wanted for her to be happy, and I guess she was. As for me, the shock wore off and I was relieved that I wasn’t going to get married.”

Related: Billy Dee Williams Says He Never Dated Diana Ross — 'But I Loved Kissing Her On-Screen' (Exclusive)

He Contemplated Suicide in the 1960s

In the spring of 1963, The Blue Boy in Black closed after 23 performances, and with no other job prospects on the horizon, Williams became depressed.

“Acting jobs were hard to get in general," he writes. "Add the challenges of having brown skin and the options were as plentiful as water in the Mojave.”

As a man who was “divorced, a father, and didn’t have a steady, reliable job or stable residence,” Williams began “questioning [his] entire life’s purpose.”

His circumstances ate at him, and he found himself unable to see a way through it. “For a brief moment, I thought about suicide. Of course, this was me being overly dramatic, but the thought crossed my mind as a way of taking control of my life and finding relief from the frustration of not working," he writes. "If I couldn’t act, if I wasn’t able to live as an artist and express everything that I knew was inside me, if I couldn’t fulfill my potential, if I wasn’t able to contribute, what was the point of this life of mine?”

He Got Fired from a Play After Whispering Dirty Jokes to Leslie Uggams

In 1967, Williams substituted and ultimately took over for Robert Hooks in the Tony Award-winning musical Hallelujah Baby!, starring alongside Leslie Uggams.

“Leslie and I knew each other from parties we had attended as kids. I was a little older than her, but we were all acquainted," Williams writes. "Her mother adored me. On and off stage, we teased and flirted with each other.”

One night, however, their flirty banter went too far. “She whispered a risqué joke to me while we were onstage. I responded immediately with an even naughtier suggestion, which I thought was funny but apparently crossed a line that she didn’t approve of, because Leslie told her husband, and I was fired after that night’s performance. The play closed shortly thereafter."

His friend James Baldwin softened the blow, Williams writes. When the writer heard what happened, Baldwin “howled and responded with something funnier—and dirtier.”

He Got Turned Down for L.A. Apartments in 1970 Because He Was Black

While Williams’ roots would always be in New York, he moved to L.A. in 1970 with his ex-wife Marlene Clark because “the TV and movie industry was out West.” Williams admits that he had “a harder time than [he] anticipated” finding an apartment in his new city.

“One landlord after another turned me down, explaining they weren’t allowed to let ‘people like me’ into their building," he writes. "I know this should have upset me more than it did...but I shrugged it off as a reality I wasn’t going to change on my own. But I wanted to be in Hollywood."

Williams eventually went into an older building off Hollywood Boulevard and got talking to the manager. "We got into a conversation about New York theater and the movies and she decided to bend the rules. ‘I’m not supposed to rent to coloreds,’ she said. ‘But you seem like a nice young man’,” he recalls.

Related: Billy Dee Williams Recalls How Upset Star Wars Fans Would Tell Him 'You Betrayed Han Solo'

He Has a Recurring Dream about His Mortality

At age 85, Williams began thinking about his mortality more frequently, and with this came a nightly recurring dream. “In [the dream], I am saying goodbye to friends and then walking to my car. Except I can’t find my car. I’m confused, lost and unsettled.”

That recurring dream has left the actor thinking about his legacy. “I feel like everyone has a purpose in life, some mission to fulfill, and based on the experiences I have had throughout my life, I feel like I have fulfilled mine," he writes. "Not because I chose it. It chose me. It’s the reason I went with situations I was in when I didn’t fully or even partially understand them. I trusted that it was meant to be.”

For more on Billy Dee Williams' life and revealing new memoir, pick up this week's issue of PEOPLE, out Friday, or subscribe here. 

Williams' memoir, What Have We Here?, is available now wherever books are sold.

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