Da’Vine Joy Randolph isn’t so sure about this Oscars thing

After wowing audiences in ‘The Holdovers,’ the actress is a favorite to win an Academy Award. Maybe then she’ll believe the hype.

Da’Vine Joy Randolph is nominated for best supporting actress at the Oscars for her performance in "The Holdovers." (ABDM for The Washington Post)
12 min

New York

Da’Vine Joy Randolph already knows the question everyone will ask when she hits the red carpet on Sunday: “So how does it feel?” She’s heard the query so much lately that she can imitate it perfectly, her opera-trained voice filling up a generic conference room as she executes a Valley-slash-Philly-girl vibrato, all high-pitched and perfunctory and existentially fraught.

So how does it fee-eel??!!!

It’s Hollywood for “hello.” Everyone should have an answer, the answer. Great! Overwhelmed! So happy to be here! But Randolph doesn’t really speak Awards Season — not like the shiny glittery things who seem to have it down. Ask her how she fee-eels and the 37-year-old Oscar nominee will answer for real.

“It hasn’t caught up to me, or rather I haven’t caught up to it,” Randolph says. “It’s still like untouchable to a certain degree.”

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We’re in the midtown Manhattan offices of Focus Features, which distributed “The Holdovers,” in which Randolph delivers a Rubik’s Cube performance that critics can’t stop turning over. She’s been collecting awards everywhere for her role as a grieving mother in the film — a Golden Globe, a SAG, a Critics Choice and, three days after our chat, a BAFTA. You would think that after all that speech-giving and question-fielding and hardware-winning, she’d know exactly how this feels. But Randolph is still processing. “It hasn’t hit me yet.”

Instead of forcing an embrace, Randolph is keeping an almost clinical distance from the hype swirling around her as she tries to dissect what it all means. Consider this example on her Instagram feed: In one video she posted in January, the actress’s expression might best be described as “over it” as an off-screen journalist heaps on the flowers. “I just want you to know my face is one way but inside my heart is crying,” an admittedly jet-lagged Randolph says as she finally laughs, realizing what she must look like.

Randolph used to feel bad for not doing it like everybody else — the ready smile and some teed-up answers. For literally not looking the part. She’s grateful, don’t get her wrong. But also skeptical. “I’m just honest. I already act for a living, so I didn’t feel like faking it,” she says.

So this weekend at the Dolby Theatre, Da’Vine Joy Randolph is showing up as herself. And after? She’ll take “a big ol’ nap.”

Is there an Oscars spirit? Some seasonal sense of enthusiasm an actor can slip on like a Christmas sweater? If there is, Randolph’s friends and colleagues have encouraged her to get into it. That includes “Holdovers” director Alexander Payne. But he also understands the reluctance.

“Sure, praise is wonderful and the ego stroke is wonderful and the encouragement to keep going, but it’s never as wonderful as actually doing the work,” Payne says. “But I do hope she comes around to it and takes some pleasure in the pleasure she brings to others.”

How do you enjoy it? Paul Giamatti practically scoffs. “I’m not the guy to ask,” says the actor, who over a 30-year career has played curmudgeons using every crayon in the box.

“Is this something you ever enjoy in the way that people understand enjoying something?” he asks. For Giamatti, an Oscars moment like the one he and Randolph are having is “a wonderful acknowledgment” that can open doors to more work.

“She and I are similar in this way. We know how to keep moving and working,” says Giamatti, who is also nominated for his role in “The Holdovers.”

In the ’70s-set film, Giamatti and Randolph play Mr. Hunham and Mary, a teacher and a cook at a New England boarding school who are stuck on campus over the holiday break with a lone student, Angus (actor Dominic Sessa). Each character has been left behind in some way. Giamatti’s by time, Sessa’s by his parents and Randolph’s by her son, who was killed in Vietnam. Mary’s grief is given the air it deserves, with Randolph delivering a performance that straddles several emotional chasms — between eruption and calm, joy and pain, sarcasm and sympathy.

And how should Giamatti’s co-star play awards season? “It’s not like it’s work, but it is,” he says. “It’s psychic, energetic work, and it’s weirdly draining. You just start to feel like, ‘Man, I can’t keep being articulate about something at this rate and this level all the time.’” But when it comes to Randolph, Paul Giamatti has the time.

“Words come to mind like ‘grounded’ and ‘flexible’ that don’t seem adequate somehow,” the “Sideways” and “Billions” star says. “There’s an image I have in my head of her putting her arms around a scene, it’s just all-encompassing. I can’t quite articulate what it is about her.” He keeps apologizing, but he keeps going. “There’s a lot of scope to it. I wish I could describe it better. She’s got big reach. You’re going to get every possible color that you need out of it. There’s a warmth — or something. With her you know every note is going to get hit right.”

Payne first saw Randolph in “Dolemite Is My Name,” the 2019 Eddie Murphy-led ode to comedian Rudy Ray Moore. Randolph played Lady Reed, a single mother and comedian whom Moore discovers on the Chitlin’ Circuit. Payne praised Randolph’s “willingness to be honest and raw and vulgar.” His reaction to seeing her on-screen was immediate: “Wow, who is that lady?”

Randolph had her own questions when they met.

“‘Listen, who is [Mary] to you?’” the actress asked Payne. “‘Is she the help?’ And I just left it at that. I wasn’t like, ‘Or is she …’” Randolph has made a career out of filling in the blanks on the page. But first she wants to make sure everyone is on the same one. Luckily, Payne’s vision for the character was panoramic; David Hemingson’s script had Mary handling much more than just her male co-stars. With that out of the way, Randolph could say, “Okay, now we could have a conversation about the art.”

Randolph has been careful while building her résumé, hoping to prove that range and quality are within every artist’s reach. You just have to make the industry see it. And you’ll certainly have to pass on work that might pay the bills but dilute the message. Hollywood is already sending her more Mary roles. She’s already on to the next thing.

“She told me early on, ‘I want to have a career where I can play anything,’” Payne says. The director has no doubts.

But that’s what everyone says about Randolph. That her talent is vast. That her credits are unexpected, especially in an industry that loves to pigeonhole. If you didn’t catch her in “The Holdovers,” then you saw her as hard-nosed Detective Donna Williams in “Only Murders in the Building.” If you didn’t realize that was her playing gospel great Mahalia Jackson in “Rustin,” then you noticed her as the lesbian drug dealer Aunt Pooh in “On the Come Up.” And if there was one beloved character to rule them all during the pandemic couch-potato years, it was Randolph’s full-bodied portrayal of Cherise in the TV remake of “High Fidelity.”

Cherise was a difficult character to cast, says Zoë Kravitz, who starred in and executive-produced the series set in a record store in Brooklyn’s Crown Heights. Cherise was based on the character Barry, played with Tasmanian-devil energy by Jack Black in the 2000 film. The producers searched “far and wide,” says Kravitz.

A voluptuous, mouthy and hilarious Black woman could easily transform into the butt of the joke — but not in Randolph’s hands. The actress pulled off a hat trick with “so much heart, so much soul, so much comedy,” says Kravitz. “She made Cherise such a human.”

The last two minutes of “High Fidelity,” which Hulu canceled after one season, are anchored by Randolph’s pure sound. After 10 episodes, the audience finally gets to hear a performance by Cherise, whose dream of launching a music career seems tragically out of reach. She strums a guitar and works through the first verse of Stevie Wonder’s “I Believe (When I Fall in Love It Will Be Forever).”

“We were all behind the monitor silently sobbing,” Kravitz says. Where Randolph is now, at the front of Hollywood’s awards conversation, was inevitable to Kravitz. “This was always going to happen. No part of me is surprised that she is at this level right now.”

One person who didn’t know this was going to happen? Da’Vine Joy Randolph.

The actress admits to having impostor syndrome “big time.” Who doesn’t these days? But Randolph can pinpoint the moment when she went from knowing where she was headed to feeling as though she’d been kicked off course.

Randolph had always been a singer. Originally from Philadelphia, she moved to Hershey, Penn., in middle school when her parents, both educators, took positions at the Milton Hershey School. Music was for Randolph what basketball was for LeBron. That gift was not up for debate. “I could see this is affecting people. That connection with the audience. No one’s really confused,” she says. In high school she attended the prestigious Interlochen Arts Camp in Michigan and later enrolled in Temple University’s Boyer College of Music and Dance to study opera. She was cast in Verdi’s “Aida” her junior year.

“Knowing this is a foreign or dying art, I wanted to make sure that when my people came and saw it, they could connect to it. And the only way they could connect to it is if I knew what I was saying and what I was doing,” says Randolph. She wanted to be more than “a singing head.”

Here’s how Randolph remembers the day her life changed: She was copying sheet music when she overheard the shouts of an acting class. When it ended, she asked the teacher to go over some of the text from “Aida” with her. “‘Like, I don’t want to be an actor,’” she recalls. “‘Just can you go through this story with me and let’s break it down.’” But to her own department, this crossed an invisible line.

“I got kicked out,” Randolph says. “Their theory was, since you want to be an actor so bad, then go be an actor.” Randolph most definitely did not want to be an actor. It was her mother, Joyce, who persuaded her to walk across the street to the theater department and enroll there. She pushed back.

“‘I don’t want to do that crap. Those people are weird,’” is how Randolph describes her reaction. But she relented and joined the weirdos and graduated on time in a blur. That swiftness led her to the Yale School of Drama. More school meant more time to think.

“I wanted to hide in the education. It bought me three more years,” says Randolph. Being the only Black woman in her class turned out to be a strange gift — at least she wouldn’t compare herself to or be pitted against someone who looked like her. And as an acting “baby,” Randolph lacked a lot of fear. She leaped. Yale was a parachute.

Two months after graduation in 2012, Randolph booked “Ghost: The Musical” and earned a Tony nomination for her portrayal of the fake psychic Oda Mae Brown. She left Broadway for TV and film roles and has been working at a relentless pace since — and yet the actress is still not completely sold on the whole acting thing.

With music there was no second guessing. Everybody knew. But at Temple, in 2009, she largely put singing in a safe-deposit box. “A protective wall came up because I knew in that moment, if you listen to this you’ll never come back,” says Randolph. “I was very like hurt by it. I didn’t want to be considered a singer who acts. No no no, I’m an actor who may sing. And I’ve been rocking that badge for a long time,” says Randolph.

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Only now — after the salve of time and perhaps the security of industry recognition — is she ready to reintroduce Da’Vine the singer to Da’Vine the actress. So she’s working on a biopic, but it’s still too fragile to share details. She’s got a working list of about five women whose stories haven’t been told — or told deeply. Ella Fitzgerald has been on that list. But there are others.

“I’m very specific and critical about what roles I’m choosing and why, because there has to be a message,” Randolph says. She wants people of color to see themselves in the characters she plays, and she wants those characters to inhabit quality productions.

“I do this for the people. It’s genuinely an act of service,” Randolph says. “I want people to know that if you have something on your heart that you can’t stop thinking about, it’s meant for you to do it and you should do it. You will do it. It’s your fate. But you should really commit to doing it.”

Not that it worked out for her that way. “Nooo. Uh-uh,” she says. Instead she was pushed backward into the deep end and learned not just to swim but to do somersaults. Maybe now she’ll learn how to soak it all in, too.

“I guess if I ended up winning it,” Randolph says of the Oscar, “at that point I could be like, ‘All right, you’re not too bad.’”

Everything you need to know about the Oscars

The 96th Academy Awards came to a close, but you can catch up with everything you missed from the 2024 Oscars and get the minute-by-minute highlights from our live blog.

Winners: Check out the full list of Oscar winners, which include Emma Stone’s surprise win over Lily Gladstone, Billie Eilish’s victory for her heartbreaking “Barbie” song and Robert Downey Jr. winning for his portrayal of Lewis Strauss.

Firsts: Wes Anderson won his first Oscar, for the short film “The Wonderful Story of Henry Sugar,” and while Gladstone didn’t win she is still the first Native American woman to be nominated for best actress.

Red carpet: See our picks for the best celebrity Oscar looks, or click through the photos from the star-studded night.