In The Holdovers, Da’Vine Joy Randolph Shines Through the Grief

Interview by Lynn Hirschberg
Photographs by Juergen Teller
Creative Partner: Dovile Drizyte
Styled by Sara Moonves

Randolph wears a Willy Chavarria opera gown; Wolford dress; Van Cleef & Arpels earrings and necklace...
Juergen Teller/W Magazine

In the 11 years since her breakout Tony-nominated role as Oda Mae Brown in Broadway’s Ghost: The Musical, Da’Vine Joy Randolph has made her mark in Hollywood in a variety of celebrated projects including the Golden Globe–nominated Dolemite Is My Name, with Eddie Murphy, and the cult favorite High Fidelity, with Zoë Kravitz. This year saw her delivering stellar turns in Only Murders in the Building and HBO Max’s The Idol, as well as a cameo as the real-life singer Mahalia Jackson in Rustin. But it’s her heart-wrenching performance in Alexander Payne’s The Holdovers, in which she plays Mary Lamb, a boarding school cafeteria manager who’s grieving the death of her child, that has left audiences—and critics—stunned. Here, the Golden Globe nominee discusses taking on the dramatic role, and why she’ll never say never to a reality singing competition.

Your character has a huge undertow of melancholy. Was that difficult for you to play?

It was challenging to play a character that had a completely different spirit, personality, tone, and rhythm than me, but the challenge to transform also made me very excited. In The Holdovers, my character is in a state of grief. She has lost her son. I wanted to display the different stages of grief, from start to finish, in the film. I thought about the people who would be watching this—so that if someone was mourning or experiencing loss, they would feel connected to my character and the film.

You filmed in Boston in the dead of winter—that must have set a certain mood.

You know sometimes when snow first falls and it's so quiet that it's loud? It's deafening almost. I knew we could not stay in this space. So I did the opposite. I would giggle and laugh and be silly on set. When I came home, I would connect with family and loved ones. I would listen to music. I stayed joyful and happy, telling lots of jokes and taking good care of myself.

You started your career as a singer.

I’m a classically trained opera singer. I thought that was my journey. I’m telling you a secret: I may be able to bridge art forms together. I would love to portray the opera singer Leontyne Price in a film. She’s in her 90s, and we’re trying to reach out to tell her story.

Do you still love to sing?

Yes, but this singer doesn’t like karaoke. The Voice and American Idol give me anxiety because I want those contestants to be so good.

Da’Vine Joy Randolph wears a Norma Kamali dress; Tiffany & Co. Schlumberger bracelets; her own shoes.

Would you ever go on The Voice? You’re probably past all that.

Listen, I’m never past anything. I’m always open to it. I think it’d be fun to go on The Voice!

Do you ever get starstruck?

Not really. But there’s something I call the “Brad Pitt effect.” I did a film called The Lost City,and he was staying in the villa next to mine. That was intense: just him being him. Once I saw him in person, I got it. It’s not just that he’s sexy; the “Brad Pitt effect” is like an aura.

Senior Style Editor: Allia Alliata di Montereale. Senior Fashion Market Editor and Menswear Director: Jenna Wojciechowski. Hair for portfolio by Mustafa Yanaz for Dyson at Art+Commerce; makeup for portfolio by Emi Kaneko for Tom Ford at Bryant Artists; manicures for portfolio by Michelle Saunders for Chanel. Set design by Peter Klein at Frank Reps. Special thanks to Ms. Bebe at Outfitters Wig Shop in Hollywood.

Produced by Connect the Dots; Executive Producer: Wes Olson; Producer: Zack Higginbottom; Production manager: Nicole Morra; Production coordinator: David Cahill; First photography assistant: Trevor Pikhart; Second photography assistant: Jeremy Eric Sinclair; Digital Technician: Brendan Pattengale; Postproduction by Lucas Rios Palazesi at Quickfix; Fashion assistants: Tori López, Tyler VanVranken, Molly Cody, India Reed, John Celaya, Kaamilah Thomas, Emily Cancelosi, Allie Kessler, Juliana Bassi, Karla Garcia, Jacqueline Chen, Cosima Croquet; Production assistants: Mateo Calvo, Aspen Miller, Nico Robledo, Griffin Koerner, Danielle Rouleau, Nicolo Battaglini, Juanes Montoya, Juan Calvo, Lily Cordingley, Nathan Gallie, Cameron Hoge, Jack Fahey, Cole Ewing, Karlie Ofstedahl; Hair assistants: Takao Hayashi, Andres Copeland; Makeup assistants: Amelia Berger, Willie Huang; Manicure assistants: Rachel Messick, Marissa Asprer; Set assistants: Christopher Crash Richard, Winston Willingham; Tailors: Irina Tshartaryan, Elma Click, Gayane Mnatsakanyan at Susie’s Custom Designs, Inc.