Oprah was 'uncomfortable' with certain moments in the Sidney Poitier doc

Oprah Winfrey still gets teary-eyed talking about her friend and mentor Sidney Poitier, who died in January. During a recent interview at the Toronto International Film Festival, where she debuted Sidney (out today on Apple TV+), a documentary she produced about the groundbreaking actor, Winfrey's deep love, loyalty and admiration for Poitier is clear. But that doesn't mean that the profile, which features starry interviews with the likes of Denzel Washington, Lenny Kravitz and Halle Berry, glides over some of the bumpier aspects of Poitier's life. Winfrey and director Reginald Hudlin (Boomerang, Marshall) wouldn't have it any other way. Read on for our conversation.

ENTERTAINMENT WEEKLY: I really enjoyed Sidney. It feels more like a film than a documentary, which is a testament to both of you.

OPRAH WINFREY: Tell us why you really enjoyed it.

I thought I knew a lot about Sidney and his career. But I learned things from this.

REGINALD HUDLIN: This was the goal.

How did you both get involved? 

HUDLIN: I got approached by Entertainment Network, which is a production company, who had cut a deal with the family to do the first ever documentary on the life of Sidney Poitier. I was immediately very excited. And as we're putting together the team, I said, "Well, let's start at the top and let's start with the best — let's reach out to Ms. Winfrey." I knew, yes, of course she can make things happen. But more importantly, it was a completely organic thing because she is one of Sidney's dearest friends. She has encyclopedic knowledge of him, and I knew with her as a partner in the making of this movie, we would make a movie that was true and honorable to the man.

WINFREY: Reggie says it's a gift that we are giving to the world about our beloved Sidney. And I say, yes, it's a gift and an offering because there's no one whom I have adored more or loved more on the planet. And his story is like no other person I even heard or read about. To be able to tell that story and literally compile the essence of this man's 90-plus-year life into two hours or less, and have the world understand who he is — that was our guardian mission. It was a mission of love and protection. To protect the story and to guard the story, and to tell it in a way that would be most honorable to his life. And that is what we have done.

October 8, 1998 Nyc Oprah Winfrey And Sidney Poitier At The World Premiere Of Beloved At The Ziegfield Theatre
October 8, 1998 Nyc Oprah Winfrey And Sidney Poitier At The World Premiere Of Beloved At The Ziegfield Theatre

Robin Platzer/Twin Images/Getty Images

One of the things I really enjoyed was the cast, the people you got to talk about him. Oprah, were you the best booker ever as far as getting everyone to do it?

WINFREY: No, I wasn't. I'm terrible at booking because when people say, "I don't know if I can do it," I go, "Oh, okay." So we have other people to pressure people to do it, or to at least encourage them to do it. We all sat down with a list of people that we wanted, and from time to time would add different people to that list.

HUDLIN: We did an enormous amount of deep research: magazine articles, media over time. He has written two very popular autobiographies. So people know a lot about Sidney Poitier. We said, How do we go to truly deep cuts, and how do we have some reveals and some insights that no one's ever heard before?

He was a very complex man and his life didn't progress in a straight line. What went into the decision to leave things in, especially some of the more uncomfortable moments? 

HUDLIN: When I first sat down with the family, I was very honest and I said, "Look, I think to really tell the story of a great man, you have to take them off the pedestal. And we have to tell a real honest story." As they say, without humps, there's no getting over. So if we don't understand the setbacks and the challenges and the flaws that make him human, that make him relatable, then you're not creating a teachable moment. So we have to see and hear that, and feel his struggle.

WINFREY: It's uncomfortable because, for me, he was the epitome of perfection. And so uncomfortable to hear that, even years later in therapy, he's still trying to get over his feelings for Diahann Carroll and what he did to his marriage and what he was worried about doing to his children as a result of that divorce. So I love the fact that we were able to tell a more full story, with flaws and all — even though I think there are very few flaws because you get to see the fullness of the man.

Everybody's heard me tell the story: [I'm] 10 years old, watching the Academy Awards and he wins that night, and I am forever changed by that moment. Because that moment seared the possibility of hope for my future. Because if he could do that, I wondered what could I do? And I sit here today, as an accomplished citizen of the world, Reggie as an accomplished citizen-filmmaker of the world, because Sidney Poitier kicked open those doors for us, and for so many other people.

I would have to say, too, that I had this dream of who he might be long before I met him. But the man exceeded every dream or every part of any imagination I could have for the kind of person he is. He was an extraordinary human being.

Sidney Poitier
Sidney Poitier

Bettmann/Getty Images Sidney Poitier and his historic Oscar for his work in 'Lilies of the Field' in 1964

I love that anecdote when you met him on your 42nd birthday and he seemed to instantly understand you, because both of you carry the dreams of other people.

WINFREY: I talked about him to everybody I knew, and certainly another documentary worth doing is Quincy Jones. Because Quincy Jones has known every human being on earth, intimately, personally, close up. He knows everybody. So Quincy Jones had a 42nd birthday party for me at his home, and he knew I wanted to meet Sidney Poitier. And when I came down the stairs, Sidney Poitier was there. I could start bawling right now thinking about it, just that moment where he said, "Oh, my dear, I've been longing to meet you." Longing. Who says longing?

HUDLIN: Sidney.

WINFREY: Sidney says longing.

HUDLIN: And he doesn't just say it.

WINFREY: When he says it, you feel like, "You've been longing to meet me, really?" And we ended up sitting in the corner for hours for the rest of the night talking. And we talked for years after.

I was wondering about your timeline shooting Sidney. When were your subjects interviewed, and when you were interviewed in relation to when Poitier passed? Because some of those interviews are very emotional, including yours at the end, Oprah.

WINFREY: He had not passed. That was before he passed.

HUDLIN: We were very fortunate that the vast majority of the interviews were before he passed. Because I feel like doing it after the fact would affect the tone.

WINFREY: Yeah, it definitely would've been different if it was afterwards.

HUDLIN: Right. So you're not delivering a eulogy, you're not telling a story with a heavy solemness about it.

WINFREY: I never thought of it that way before. That's good, you're right!

HUDLIN: We had all this in the can and we were, I would say, 90 percent shot. And then he passed and then I had to climb out of my own head because there's no outside pressure that can match the pressure I put on myself to get it right. And then I was like: Stop, just stop. Just go back to work.

To me, one of the most important interviews was speaking with his first wife and the children from that first marriage. And they were so insightful and so honest and so real. And that's why I feel like we live up to the name Sidney, because Sidney speaks to a level of familiarity. It's a first-name basis. When we picked everyone, we said we want to talk to people who knew him.

WINFREY: Knew Sidney, not just Sidney Poitier, but Sidney.

HUDLIN: He has a planet of admirers, but who knows him? And talking to Morgan Freeman, talking to Barbra Streisand, talking to Robert Redford, who are contemporaries, who know the man intimately. Denzel Washington, they lived down the street from each other and he would just show up in sweatpants and hang out. So they have a different take on him. And that's the take we wanted to invite the public to know.

Was there anybody on your casting wishlist that you didn't get?

WINFREY: [turning to Hudlin] Was there anybody else you wanted that we didn't get? Because I thought the big get was getting [Poitier's first wife] Juanita. I'd seen a version of the film and I remember saying to you, "I think who's missing here is Juanita."

HUDLIN: That was the get, because I just thought there's a giant story there. It's like in physics, there's a black-hole effect. I knew she would be that thing that would make everything else in the celestial make sense.

WINFREY: And the actress from Guess Who's Coming to Dinner? [Katharine Houghton]

HUDLIN: Oh wow, she was spectacular.

WINFREY: The fact that she didn't know that the kiss was such a big deal. I'm like, "What world were you living in?" All of us knew that was a very big deal.

HUDLIN: But for me, her comment when Sidney said, "Oh, this is my last movie because Black audiences are done with me, because the political mood has shifted in the country," that's a powerful insight. Because Sidney was so aware, so plugged into what was happening with people. Thing about movies, they take at least a year. So he lines up all these movies, he's working back to back. But in the time he finally gets to that movie, he knows: This is an important movie. I'm committed to it. I'm going to do it. But I also know for right here, right now, the mood of the Black audience has shifted and it's time for me to transition. And he always knew the right moment and the right time to do stuff. And he always did the right thing. He says, Look, I don't have to be the Black superhero anymore. Now there's all these new actors and new movies being made. Now I can be funny. I can do comedies…

WINFREY: …I can direct. I want to direct.

HUDLIN: Those instincts are extraordinary.

WINFREY: What you come away with after seeing this film, aside from this great film star and father and human being, is the essence of knowing who you are. And I think that that is the key to success for anybody who wants to really soar in their lives, is starting with your own personal identity. And from the very beginning of the film, we see a young boy growing up in a country where race was not an issue for him. The story he tells about being 10 years old and not knowing what a mirror was, because he'd never ever seen himself in the mirror. So he was not raised with those definitions of limitation, of who you can be and what you can be. He was raised with this firm belief system in character, in integrity and respect for yourself, and that came from his parents.

And so I think everybody watching comes away with that. That no matter what you do in your life, if you have that, that is the foundation for greatness that we see so visible in Sidney Poitier.

Sidney, available on Apple TV+, is out today.

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