Inside My Collection

Art Market

Inside My Collection: Roxane Gay and Debbie Millman

Ayanna Dozier
Apr 2, 2022 1:34PM

Roxane Gay is known for her laser-sharp wit in cultural criticism and nonfiction works, but lesser known is her growing practice as an art collector. Her partner—writer, artist, educator, and curator Debbie Millman—has steadily amassed an impressive trove of contemporary art that ranges from outsider art to Andy Warhol. Together, they are building an art collection across their homes in Los Angeles and New York that reflects a shared vision, and allows them to live with art that supports their cultural missions.

While Gay and Millman are unifying their collections, their distinctive approaches to how and what they collect are still visible. Millman’s background in design (and role as the host of the pioneering podcast Design Matters) informs the art that attracts her the most. Additionally, her rich lived experience in New York, where she was born and raised, has shaped her collection—including works by Warhol, Jean-Michel Basquiat, Karen Kilimnik, and other esteemed artists that she acquired through personal connections and chance encounters. Millman’s robust engagement with the art world for nearly 30 years provides a strong foundation for the collection she now shares with Gay.

Installation view, left to right: Dennis Osadebe, Stand For Something, 2019; Kezia Harrell, End, 2020. Photo by Elizabeth Carababas for Artsy.

Installation view, Nekisha Durrett, Sandra Bland | Killed by police on July 13, 2015 | Age 28, 2020–21. Photo by Elizabeth Carababas for Artsy.


Gay was born in Omaha, Nebraska, to parents of Haitian descent. Coming from an academic background, Gay has emerged as a key critical cultural voice to a large public audience over the past decade. Although she grew up with parents who collect, Gay has only recently directed her attention towards an art collection of her own.

Gay sees her art collection as a powerful tool that can transform the image of what an art collector looks like to a popular audience. Moreover, she expressed her desire to carry over her critical interests in cultural identities to the realm of art collecting, where she can directly support women of color and queer artists through buying their work and sharing their visions.

During a conversation this past March, Millman and Gay discussed their collecting origins, the artists they admire, and the roadblocks that can render art collecting inaccessible for emerging collectors.

Installation view, top to bottom: Stanza from Maximus, To Himself by Charles Olson, crafted by Katherine Good. Tejo Remy, You Can’t Lay Down Your Memories Chest-of-Drawers, designed in 1991, fabricated in 2008. Photo by Laurel Golio for Artsy.

Installation view, artist-designed plates, clockwise from top left: Lawrence Weiner, James Victorei, Ed Ruscha, Sophie Calle. Center: Virgil Abloh x IKEA “MARKERAD” Wall Clock. Photo by Laurel Golio for Artsy.

Ayanna Dozier: How and when did you each start collecting in earnest?

Debbie Millman: About 30 years ago. I was into outsider art and enthralled by the work that Ricco/Maresca Gallery was showing. I had a friend, Brian Rutenberg, who signed a deal to be represented by them, and I began collecting his work.

Roxane Gay: My parents collect Haitian art, so I knew about art collecting through them. I never imagined art collecting was within my means. I always assumed you needed to have Basquiat-level money and I am just a writer. But then I met Debbie, and I learned there are so many price points below Basquiat and from there, I started to build my collection.

Installation view, top row, left to right: Kahlil Robert Irving, Music Memorial in Film [(Greeting Screening Chained) Daily Ritual & tribute (TERROR)], 2019; Alison Saar, Congolene Resistance, 2021; William Kentridge, Ref. 56, from Universal Archive, 2012; Bisa Butler, Daughter Of The Dust, 2020; Adrian Piper, Forget It, 1991; LaToya Ruby Frazier, Holding flag laying at the edge of Pier 54 and the Hudson River, 2014. Middle row, left to right: Glen Ligon, Black Rage (back cover), 2019; Roy Lichtenstein, Spray Can, 1963; Hank Willis Thomas, All Li es Matter, 2019; Asha Schechter, Park La Brea (Marbled), 2013 Bottom row, left to right: Mark Bradford, Mijo, from Can You Feel It?, 2004; Mario Uribe, Friendly Fire; Sadie Barnette, Observation, 2017; Fred Tomaselli, July 5, 2012, 2012. Photo by Elizabeth Carababas for Artsy.


A.D.: What happened after that first work that you purchased? How did your collection grow from there?

R.G.: I discovered Artsy and Artspace and learned about auctions and started collecting in earnest. It’s addictive.

A.D.: Is there a piece—or are there multiple pieces—that you consider the beginning of your collection?

D.M.: I started with Benjamin Franklin Perkins’s Ten Commandments for Successful Daily Living. And I knew someone who worked for Andy Warhol, so I was able to get a small Marilyn print that was signed by him. Gavin Brown at the time was working at a gallery, and I was able to buy a Karen Kilimnik for somewhere around $500, which at the time was a lot of money for me. That piece was later included in an exhibition, which I was proud of.

R.G.: I started with a small Lichtenstein print Debbie gave me as a gift and then I bought a tapestry by Gio Swaby from the Claire Oliver Gallery. I love it so much and sadly it’s leaving us for three years because it is going to be on tour in an exhibition of Gio’s work at museums like the Art Institute of Chicago and the St. Petersburg Art Museum and others.

Installation view, Richard Serra, Ishmael’s Edge, 1987. Photo by Laurel Golio for Artsy.

Installation view, Jenny Holzer, Protect Me From What I Want, 1990. Photo by Laurel Golio for Artsy.

A.D.: How do you describe your collection? Do you collect thematically?

R.G.: It’s a range. We’re really interested in supporting and collecting women, queer, and people of color artists. I am specifically invested in Black artists, Black women artists, and their experiences.

What Black women are doing artistically is so sophisticated, like Sadie Barnette, for example. Barnette, who is from Oakland, has a painting about her father [Rodney Barnette]’s FBI file. The concept is so fierce; that she could take something so systematically horrible and make a compelling artwork out of it is just fascinating.

D.M.: I am drawn to typography and text-based/-oriented works. I think it speaks to my previous career as a designer and my love of language.

Installation view, left to right: Alexandra Grant, I was born to love not to hate (16), 2019; Alexandra Grant, I was born to love not to hate (17), 2019. Photo by Elizabeth Carababas for Artsy.

A.D.: Can you tell me about a couple other works in your collection that are especially meaningful?

D.M.: I want to live with art. I like being surrounded by beautiful things, and I think it is important to live with the art I want around me. It is almost as if [the artworks] are magical amulets that restore you and your home through their presence.

The most prized piece in my collection is a Jean-Michel Basquiat, and it means so much to me. I had always wanted a Basquiat, even back then, but he was always out of my budget. I remember going to Robert Miller Gallery to see if he had any for sale.

Installation view, left to right: The Connor Brothers, I Sometimes Feel that God, in Creating Men, Somewhat Overestimated His Ability, 2019; Debbie Millman, My Heart, 2019. Photo by Elizabeth Carababas for Artsy.

Installation view, left to right: Edwin Schlossberg, As Words, from “Tidal Gestures” series, 1990; James Maurelle, Who’s Next, 2019; James Maurelle, Friday Night, 2021; Wells Chandler, School Bois, 2019; Nekisha Durrett, Sandra Bland | Killed by police on July 13, 2015 | Age 28, 2020–21. Photo by Elizabeth Carababas for Artsy.

Back then, I just bought what I could afford. I asked him if he had anything related to Basquiat, even a napkin that he signed. I remember my friend pointing out a chair Basquiat had sat in, and so I took a picture in the chair just as a way to be near Basquiat’s energy, and I still have that photograph [laughs]. Finally, a few years go by, and I get a call saying that [Miller] had something if I wanted to come in and see it; he could not quite make out what it was. It was a sketch, and he sold it to me for $1,000. I didn’t know what it was either, but I bought it immediately.

Sometimes, it takes a while for you to interpret or make sense of artwork and I spent forever staring at it to figure it out. Then one day, I looked at it and realized it was a face split down the middle: one side black and the other side white. The scribbled bit beneath the face said “allies,” and when it clicked, it just blew me away. Of course, when I told Robert about this, he immediately wanted it back, but it was too late.

Stanza from Maximus, To Himself by Charles Olson, crafted by Katherine Good. Photo by Laurel Golio for Artsy.

R.G.: For me, it would be a painting by Brenna Youngblood that I got at Roberts Projects in Los Angeles. It is the one piece that I do not have a place for because it’s so big but it’s in my house nonetheless and I enjoy seeing it every day.

D.M.: Our next move will revolve around our art collection and ensuring that we can have space for each piece.

R.G.: The painting is so unique because it is a red canvas with a black shoe attached to it. And the shoe, like all of Youngblood’s work, has so much personal significance to her. I just stare at it and think: How did this come together? I find it really inspiring.

There’s also an M. Florine Démosthène I bought through Mariane Ibrahim Gallery at either Frieze or The Armory Show that I also love. That work is very special because I was having such a hard time with the galleries at the fair, and the gallerist from Mariane Ibrahim was so nice. Démosthène works with collage and creates these thick, lucious brown bodies. I would own everything she ever created if I could.

Installation view, left to right: Sam Winston, Dictionary Story, 2020; Lorraine O’Grady, Cutting Out CONYT 10 Year, 1977/2017; Deborah Roberts, Untitled, 2021. Photo by Elizabeth Carababas for Artsy.

A.D.: What do you enjoy most about being a collector?

D.M.: I love living with art. I don’t buy art to resell it, so the work I buy really is always meaningful to me, and pieces I want to live and engage with every day.

R.G.: As a writer, I take a lot of inspiration from looking at art. I can’t have all the creative gifts, I can’t even draw a stick figure, so I enjoy looking at what other people are capable of. That always invigorates me. I love engaging and connecting with artists in that way where I can see their audacity. I also love supporting other artists.

When you buy from auction, artists do not see that benefit, unfortunately. I have, though, bought some works recently that had a contract attached to them where the artist receives a kick back. I really like that model and hope to see it continue at all points of sale.

Installation view, Käthe Kollwitz, Städtisches Obdach (Urban Shelter), 1926. Photo by Elizabeth Carababas for Artsy.

Installation view, background to foreground: Gio Swaby, Love Letter 1, 2018; Shantell Martin, Martone Cycling Co. bicycle, 2015. Photo by Elizabeth Carababas for Artsy.

A.D.: Can you tell me a bit about your experiences buying art online and using Artsy?

R.G.: I love the nature of buying from Artsy. You make a bid or inquire and then the gallery responds. Sometimes there’s a little back-and-forth, and if you want the piece after you pay, the art shows up.

There’s one advisor who works there, Caroline Perkins, who I really love working with. She has been really helpful in putting interesting works on my radar and tracking down work from artists I am looking for.

One time, I purchased a piece that arrived damaged. I contacted Artsy and they handled it at no cost. They sent an art restorer, which says a lot as Artsy is just the middleman. They went out of their way to make it right.

Installation view, left to right: Jonathan Adler Georgia Orb; Ai Weiwei sunflower seeds; Kenneth Fitzgerald book. Photo by Laurel Golio for Artsy.

A.D.: How do you prefer to collect? Via galleries, auctions, fairs, online, directly from the artist? And how do you build relationships with galleries?

D.M.: I don’t do art fairs. I do enjoy auctions and online. I’ve had a lot of good luck with eBay.

R.G.: I like walking around art fairs. It’s nice to see all the different types of galleries and how they choose to curate the show, whether it’s a range of artists or a single artist. There are so many different types of work in one place, although so much of it is very expensive. I also like auctions, especially benefit auctions, and, when possible, to buy directly from the artist.

Galleries do frustrate me. I like how a gallery can curate an exhibition, but there’s so much bullshit there. It really shocked me as I started to build my collection and began trying to buy from galleries directly. I learned through this process that racism is more powerful than capitalism. And I’m stubborn, so with some of these places I will push back, because I deserve to be here, but I also need to learn to let go because I’m not going to reward bad behavior with good money.

Installation view, left to right: Jenny Saville, Chapter (for Linda Nochlin), 2016/2018; Emma Hopkins, Mixed Emotions I, 2017; Kandis Williams, The Bathers of Acheron, 2018. Photo by Elizabeth Carababas for Artsy.

A.D.: What have your experiences been with galleries? And what led you to buy via Artsy?

R.G.: I have had mixed experiences with galleries. Some have been lovely—Claire Oliver, Roberts Projects, Wexler Gallery, Sapar Contemporary, Vielmetter Los Angeles, to name a few—are wonderful galleries that represent their artists so well. But sometimes, buying from a gallery feels like you are auditioning to spend your money. They’ll say things like, “We would love to know more about you,” because if they don’t know who you are, they want to be sure your collection is important enough to place their artists into. For Black collectors, especially, that can be tricky. Or they basically blackmail you by offering you a work that is not the work you want to buy in order to establish a “relationship” and only then will they “allow” you to buy the work you’re actually interested in. As someone who is not in the art world, I find that to be wild.

What I love about Artsy is the transparency. There are no extra fees or hidden pieces to search for. It’s very upfront. The price is the price, and then you know you are going to pay out of the ass for shipping, but that’s it. I appreciate how Artsy reduces some of the barriers for building a collection.

Installation view, left to right, Shepard Fairey, Noise & Lies (set of 2), 2018; Lonnie Holley, Black in the Midst of the Red, White and Blue, 2017. Photo by Elizabeth Carababas for Artsy.

Installation view, top to bottom: Christine Wang, Food, 2016; Jean-Michel Basquiat Case Study® Furniture chair by Modernica; Debbie Millman, PomPom Table, 2020. Photo by Elizabeth Carababas for Artsy.

A.D.: What are your white whales?

D.M.: Ed Ruscha’s Statistical Significance (1981) because it’s a term often used in branding and marketing and is at the intersection of my interests in art and commerce. I tried bidding on Statistical Significance when it was at auction at Christie’s and lost out because the price went past the limit I had given myself to stay out of trouble. The next time it hits the market, it will likely double in value [sighs].

R.G.: My white whale is any work by Jordan Casteel. I am trying to buy one of her works but it is hard to find on the secondary market. I also want a piece by Bisa Butler. There’s a waiting list, which we’re on, but her work is magnificent.

Installation view, Jenny Holzer, Certainly sex, 2018. Photo by Laurel Golio for Artsy.

Installation view, left to right, John Baldessari, Heaven and Hell, 1988; Keith Haring Kids’ Chair. Photo by Laurel Golio for Artsy.

A.D.: Have you collected works together?

R.G.: We recently bought our first piece together, and it was a Guerilla Girls portfolio containing a complete archive of their work. Fun fact: it was delivered by “Käthe Kollwitz.”

D.M.: It’s exciting because starting to collect together says, “I share this vision with you,” which, really, we already knew, because we’re married.

R.G.: Agreed.

Portrait of Debbie Millman and Roxane Gay with Jean-Michel Basquiat, For Leonardo, 1983. Photo by Laurel Golio for Artsy.

A.D.: Who are the artists you’re excited about now?

R.G.: Derek Fordjour. He has a show at David Kordansky Gallery in L.A. that includes a magic show directed by Numa Perrier. I can’t wait to see that. I also recently interviewed Genesis Tramaine, whose work I am obsessed with. Her passion is real and she just opened a show this week at Almine Rech in New York. I also love Amani Lewis.

D.M.: Roxane speaks for us both. She has great taste.

A.D.: Where would you advise a new collector to begin?

D.M.: Buy what you can afford and only buy what you love.

R.G.: Same.

Ayanna Dozier
Ayanna Dozier is Artsy’s Staff Writer.