MFA students at New York’s Academy of Art got a rare treat when they were invited to peer into the private collection built by the legendary New York writer and art world tastemaker Glenn O’Brien and his wife Gina Nanni, to select works to pair alongside their own for the school’s “Eye to Eye” exhibition series (on view through March 14).

Nanni and her late husband assembled an enviable collection of several hundred objects, including multiple pieces by Andy Warhol and Jean-Michel Basquiat, both of whom were close friends. O’Brien, a key fixture of downtown New York, was at different periods editor-in-chief of Interview Magazine, creative director of Barneys, and a style columnist for GQ. Nanni is an art world publicist, who works with artists including Marilyn Minter, Laurie Simmons, and Jamie Nares.

We caught up with Nanni to speak about her own journey into collecting with her late husband, and the potentially explosive Tom Sachs installation she owns.

Gina Nanni and Glenn O’Brien in 2008. Photo by Billy Farrell/ Patrick McMullan via Getty Images.

What was your first purchase (and how much did you pay for it)?

Two Rauschenberg prints—one was on paper, and the other was an identical image but with fabric collaged on it. The pair was $500 in the late 1980s—a lot of money for me back then. I wasn’t even 21.

What was your most recent purchase?

I just bought a work online that hasn’t arrived yet. I guess I shouldn’t talk about it because I am still hoping I like it in person… but before that I think it was a great little painting by Pam Glick, from The Journal Gallery. It’s got yellow squiggles on a black ground. A grey line dissects the canvas. Intriguing work.

Which works or artists are you hoping to add to your collection this year?

I really wanted a work by Alex Kwartler at Magenta Plains that was sold before I saw it—I’d love one of his works.  I also really like Chris Martin.

Gina Nanni sitting underneath a Basquiat Untitled—Car. Courtesy New York Academy of Art.

What is the most expensive work of art that you own?

A Basquiat, undoubtedly, not sure which one. My husband was one of the artist’s very early champions and a close friend. He kept a lot. Aside from that it’s hard to know. I usually don’t pay attention to the values, except when we have to update the insurance every few years. Once in a while, there is a shocking rise or fall…

Where do you buy art most frequently?

I buy work from all kinds of sources. Often from the galleries that I work with, at art fairs, or at auction. I am lucky to work with some great galleries and artists, and am exposed to so many interesting things that I wouldn’t otherwise see.

Is there a work you regret purchasing?

Hmm… I don’t think so? My husband used to buy work, then on the rare occasion he might decide that he’s not into that artist anymore. I definitely regret a few things that he bought. Our taste was aligned 95 percent of the time. But that 5 percent was annoying. I bought a fair amount of work on my own in the past five years, and definitely have no regrets.

Andy Warhol, Untitled Over 40, which is part of the “Eye to Eye” exhibition. Courtesy New York Academy of Art.

What work do you have hanging above your sofa? What about in your bathroom?

Above various sofas I have a very large Dash Snow photograph, a painting on mirror by Stefan Brüggemann from his “Headlines and Last Lines in the Movies” series; a gorgeous colorful painting by Ouattara Watts, a Richard Prince t-shirt painting, and a work by Jonah Freeman and Justin Lowe, among some others.

Bathrooms are a great place for small work that needs to be seen close up, or work that can be a bit risqué. I like to rotate the bathroom art fairly often. Mine now have Mike Bidlo’s urinal drawings; Walter Robinson painting of Q-tips and Vaseline; a Joseph Kosuth neon work, Satisfaction; a Warhol photo of Fred Hughes urinating in a Paris street; some Ray Johnson collages; two Sara Van Der Beek Roman Women c-prints, and a Laurie Simmons underwater photograph of my son Oscar, among others.

What is the most impractical work of art you own?

Definitely a certain Tom Sachs work. It’s a sculptural installation that consists of a group of weapons, including a chainsaw and gasoline. I never actually asked if there was real gasoline in the container, or if it’s just colored water. Knowing Tom, it’s probably real.

Gina Nanni with Jamie Nares, Untitled (2005), and in the background an African work from the estate of Fred Hughes; a painting by Robert Hawkins, Jesus Waterskiing, and a Richard Prince “Protest” painting. The clay nose sculpture is by Peter Nadin. Courtesy New York Academy of Art.

What work do you wish you had bought when you had the chance?

So many great artists were very undervalued in the 1990s and early 2000s. Romare Bearden, Barkley Hendricks, Marisol. And Martin Wong—we were lucky to get one just before his prices went insane. I was also bidding at an auction once for a Judy Chicago plate, a study for The Dinner Party. It was before her comeback, and was insanely cheap. I think I got distracted and missed it. It went for just a few thousand dollars. Incredibly stupid of me.

If you could steal one work of art without getting caught, what would it be?

Now this one is really hard! Perhaps a Renaissance era work. Loving a painting and wanting to own it are very different—I don’t think I’d want a religious themed work. Maybe a Titian or something like Van Eyck’s Arnolfini Portrait…