WCW: Oprah Winfrey


Sure, she’s every woman, she’s a legit phenomenon, but she’s used her powers for good and for frock flicks when she’s had a chance! In the few serious acting roles she’s taken, Oprah Winfrey has made a point of championing African-American women’s history on screen, with a side of fine 20th-century literature. So let’s get real and get some Oprah in historical costume.


Sofia in The Color Purple (1985)

Winfrey says this Alice Walker novel (which begins in the early 1900s) is one of her favorite books and she was thrilled and nervous for this first acting opportunity. In Collider, she admitted:

“At the time, I only had two weeks vacation. I was doing 220 shows a year, and I only had two weeks for vacation. But I needed two months to film The Color Purple and my bosses were like, ‘Get your ass back here because AM Chicago is what’s important. That’s what you signed up for.’ And I was like, ‘Please just let me have two more weeks.’ So, I gave up all of the vacation weeks in my contract, in order to be able to do that movie. I said, “Okay, I won’t take a vacation for the next five years, if you just let me finish this movie.” And when AM Chicago became successful, in less than six months, people started calling it The Oprah Show.”

Oprah Winfrey, The Color Purple (1985)
Oprah Winfrey, The Color Purple (1985)

The costumes by Aggie Guerard Rodgers (who also did Return of the Jedi before and Beetlejuice since) were nominated for an Oscar.



Mrs. Thomas in Native Son (1986)

Adapted from a controversial Richard Wright novel, set in 1940s Chicago, this film had mixed reviews, but Oprah’s performance was praised.

Oprah Winfrey, Native Son (1986)



Mattie Michael in The Women of Brewster Place (1989)

Based on a novel by Gloria Naylor, this miniseries was ahead of its time and under-appreciated. It focused on seven working-class African American women in the 1960s, was strongly feminist, called out men for behaving badly, and positively portrayed a lesbian couple. Winfrey says of her acting and producing of this series, at the same time as her talk show:

“I delved into a television series for awhile, with The Women of Brewster Place. I actually thought that I could film a dramatic weekly series, and do that daily show. I nearly died. I just realized that the work of the show, and my intention behind doing the show every day, was to be a light in people’s lives and be able to bring information in such a way that they could be lifted by that. It just consumed so much of my life and time that I learned that I wasn’t going to be able to do both.”

Oprah Winfrey, The Women of Brewster Place (1989)

The characters may have been poor, but they weren’t dingy, thanks to Daniel Paredes’ costume design.

Oprah Winfrey, The Women of Brewster Place (1989)

Look at these fabulous ladies!



Mattie Michael in Brewster Place (1990)

A short-lived sequel to The Women of Brewster Place, continuing their stories and adding a few characters.

Oprah Winfrey, Brewster Place (1990)



Sethe in Beloved (1998)

Oprah Winfrey spent a decade trying to get Toni Morrison’s Pulitzer-Prize winning novel of post-Civil War horror made into a movie. This was such a labor of love, and while it wasn’t a box-office success, it’s a hugely compelling film. Colleen Atwood’s Oscar-nominated costumes help create some pivotal moments. Winfrey said of her inspiration:

“I called Toni Morrison and I said, ‘Miss Morrison, I just finished reading Beloved and I just want to know if people tell you that they have to go over the lines, again and again.’ And she said, ‘That, my dear, is called reading.’ And so, I started talking to her about the rights to the story. She said that she didn’t think it could be made into a movie. But 10 years later, we actually did it.”

Beloved (1998)

The literal scars of slavery.

Beloved (1998)



Gloria Gaines in Lee Daniels’ The Butler (2013)

Most of the film follows Cecil Gaines (Forest Whitaker) as a White House butler from the Eisenhower to Reagan administrations, and Oprah plays his wife. She’s a complicated character with affairs and addictions, plus dealing with their two rebellious sons. Oprah commented on her part in The Butler:

“I’m a historian of my own history — of African American history. I believe that when you know who you are you have the ability to move forward, not only with your own strength but with the strength of your entire ancestry. I am the daughter of a maid, and my grandmother was a maid, and her mother was a maid, and her mother was a slave. I feel validated by the war that the butler and his entire generation fought in their own way. And the fact that there’s another generation of freedom writers and freedom fighters, because of evolution and growth and change, decided they weren’t going to do that anymore. Both wars were necessary for their time.”

Oprah Winfrey, Lee Daniels' The Butler (2013)

Worried mom.

Oprah Winfrey, Lee Daniels' The Butler (2013)

But sexy in the ’60s!



Annie Lee Cooper in Selma (2014)

She makes a small but crucial cameo in the story of Martin Luther King Jr.’s voting rights campaign in 1965. Winfrey told MovieMaker Magazine why she agreed to this role:

“This is for every other woman and man in my history who took that walk to the registrar’s office and was turned down and then went back home and tried it another year and then went back and tried it another year … This was Annie Lee Cooper’s fifth time. When you think about what it takes to keep getting up and saying ‘I will’ and ‘I can’ in the face of an entire society that says you cannot and you will not … I just wanted to take the few minutes in that walk and pay tribute to all of those people. That’s why I said yes.”

Oprah Winfrey, Selma (2014)



Deborah Lacks in The Immortal Life of Henrietta Lacks (2017)

She’s playing a modern woman, Henrietta Lacks’ daughter, but the story flashes back to the 1950s during Henrietta’s life, so I’m including it. In the New York Times, Oprah discussed why she made this movie:

“I wanted to tell the story because I lived and worked in Baltimore as a young reporter for eight years, and I never in all those years of reporting, of being involved in the community, going to church every single Sunday at Bethel A.M.E., never once heard the name Henrietta Lacks. So I thought when I read the book, ‘Wow, if I don’t know this story, I’m sure that there are many many other people who also don’t know.'”

Oprah Winfrey, The Immortal Life of Henrietta Lacks (2017)



What’s your favorite historical movie or TV role of Oprah Winfrey’s?


About the author

Trystan L. Bass

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A self-described ElderGoth, Trystan has been haunting the internet since the early 1990s. Always passionate about costume, from everyday office wear to outrageous twisted historical creations, she has maintained some of the earliest online costuming-focused resources on the web. Her costuming adventures are chronicled on her website, TrystanCraft. She also ran a popular fashion blog, This Is CorpGoth, dedicated to her “office drag.”

16 Responses

  1. LadySlippers

    I’m absolutely thrilled you are featuring Oprah!

    I adore the fact that Oprah clearly thinks about the roles and movies she chooses to be in. While not a Frock Flick, but her (and all the costumes) in A Wrinkle in Time are amazing.

    But I’m torn, my favourite roles Oprah’s been in are either, A Color Purple or Beloved. She gave her all in both roles. I’d probable lean towards Beloved because that book is one of my favourite books ever and the movie didn’t get the acclaim it so deserved.

    • Trystan L. Bass

      Gawd, Wrinkle in Time was SO BEAUTIFUL! Not historical, but great eye candy.

      Oprah’s part in Color Purple was smaller than Beloved, where she carried the whole film. But I just rewatched Purple this weekend & damn it’s good. If Whoopi had been in more historical pix, I’d give her a WCW — she’s really underrated as an actress, she does drama as beautifully as she does comedy.

      • Nzie

        Ah, I wish she’d had or used (not sure how involved she was) some influence to make Wrinkle in Time LESS beautiful. I mean, yes, visually appealing, but that entirely missed the point of the three Mrs. characters, and really the story. There’s a lot of things out there glorying in beauty; I wish they’d been comfortable leaving them as weird and kind of ugly (at least in their clothes). Such potential—very talented people at all levels, but imo a fundamental misunderstanding of the story. BUT it’s good to remember well the considered thought she’s clearly put into her forays into film. We’re lucky Oprah uses her powers for good!

    • M.E. Lawrence

      I love her lack of vanity. Some deeply famous females insist on looking young-and-gorgeous, whether appropriate or not; O.W. always respects the part. (But here’s where I get to complain that “Beloved” wasn’t made earlier. Fine though Oprah was, Cicely Tyson would have evoked pity and terror in equal measure. Has F.F. saluted her lately?)

  2. ljones1966

    I’m amazed that she only had a few roles in her career. Winfrey really is a good actress. I was especially impressed by her performances in “The Color Purple”, “Beloved” and “The Butler”.

  3. Lady Hermina De Pagan

    I would love to see Oprah take on the role of Elizabeth Keckley or Sojourner Truth. She is such a subtle actress and has no trouble looking busted in a role. My favorite role of hers is Mattie in the women of Brewster Place. That scene of her in the rain smashing the brick wall at the end of the mini series is gut wrenching.

    • Trystan L. Bass

      Oh yes, either of those would be excellent roles for Oprah! Related, why no Sojourner Truth biopic yet? Hollywood, get on that! Keckley was at least a minor character in Lincoln, the one w/Daniel Day Lewis, but she deserves more too.

      • Mary Fields

        A Sojourner Truth biopic would be so fantastic, as would one about Elizabeth Keckley. I’d really love to see one about Bessie Coleman, with Janelle Monae playing her.

    • Erin E.

      Ooo! What a good idea re: Elizabeth Keckley biopic! And Oprah would be fantastic to play her! And I also loved her in Brewster Place.

  4. Mari

    Oprah was brilliant in The Color Purple. I just recently read Native Son and now I want to seek out the movie.

  5. Susan Pola Staples

    My favourite Oprah roles are in The Color Purple and Beloved. Her expressions were incredible and her acting conveyed such emotion. Especially in Beloved, one of my favourite Toni Morrison novels, where she made a horrid but understandable choice.

    I also enjoyed The Women of Brewster Place.

    I would enjoy a Sojourner Truth miniseries or biopic. I’m surprised no-one hasn’t made one.

    Also more movies from Toni Morrison books.

    I don’t know if this is a place for it, but I want 2 Oscars for costumes this year. Ruth Carter for Black Panther and Sandy Powell for The Favourite.

    Also are Beale Street and
    Black Klansman too modern for review?

  6. Kathryn MacLennan

    I watched The Women of Brewster Place when it first came out in 1989. I was all of seven years old, but I remember it vividly. It had a huge effect on my seven-year-old psyche. I couldn’t understand why people were so mean to that nice lesbian couple. They just wanted to live their lives and put olives in their meatloaf!

  7. Erin E.

    Ohhh! Women of Brewster Place! I had forgotten about that movie! Thanks for the good (also sad) memories!