Before Robert Rich ever met Winona Ryder, he loved an image of her. “It was her Gap ad that Annie Leibovitz shot,” said Rich. “I was so in love with that image. A girlfriend of mine worked at the Gap, and I begged her for it and she would not give it to me.”

More than two decades later, Rich and Ryder have created an archive of their friendship that spans thousands of photos. From the steps of the Met Gala to Ryder’s bathroom floor, Rich has been documenting one of Hollywood’s most famous—and most private—actors one image at a time. Eventually, Rich became the “Shnookie” to her “Shnookums,” as they lovingly refer to each other. “It was kind of surreal, having always admired her,” Rich recently told Vanity Fair. “I had to pinch myself in the beginning.” Now, in collaboration with Francesca Sorrenti, with a foreword by Marc Jacobs, he has assembled a collection of intimate photos that showcase Ryder like never before— through the lens of one of her best friends.

Rich and Ryder’s decades-long friendship began in 1999, when Rich was working his dream job as vice president of public relations of Marc Jacobs stores. As luck would have it, Ryder walked into a store. “I said, ‘I love Girl, Interrupted,’” which had just come out, recalled Rich. “She said, ‘That’s a girls movie.’ And I said, ‘Well, I’m a girls movie kind of guy,’ and the rest is history.”

At the time, Rich’s office at the Marc Jacobs store on Mercer Street became what he called a “secret clubhouse,” with a revolving door of models and celebrities popping in on any given day, from Kate Moss to Grace Jones to Sofia Coppola (with her famous father, Francis Ford Coppola, in tow). “We’d go down to the basement, past all the racks of clothes,” said Rich. “I had a big room full of samples that I let them play in, and we’d play dress-up in my office.” He always had his Polaroid camera in arm’s reach to capture the moment, a habit he picked from Keith Haring at the Pop Shop in the ’80s, where Rich previously worked.

Just as he had done to his childhood bedroom growing up, Rich plastered his office wall with these Polaroids, putting them alongside magazine clippings, posters, and anything that would stick. The massive collage became a fixture of his space and the backdrop to so many photos that would wind up in the book. “Somebody would come in, and if they weren’t on my wall, they would send me a picture,” said Rich. “The wall got layered over 17 years. Layered and layered and layered.”

In advance of Winona’s (IDEA) release, Rich caught up with Vanity Fair to flip through the forthcoming book and discuss capturing friendship in photographs.

Vanity Fair: **I recently spoke to your good friend Sofia Coppola about her Archive book. Did you take any inspiration from that while working on yours?**

Robert Rich: It’s beautiful. We both always loved collages. She always loved my wall. She put it in one of her books in 2003. It was a book of her favorite images, and my office wall was one of them.

I could see the parallel between your famous office wall and the Bruce Weber photo of her office.

It’s the ‘If you put a picture up of someone, they will come’ kind of thing. And I love magazines. When I love a picture, I rip it out and put it up. I love falling in love with a photograph.

Where were you storing all of these photos before you started working on the book?

Shoe boxes. They’re still in shoe boxes. But now they are separated by who they are. I have a box of Sofia [Coppola] and a box of Kate Moss.

Who else do you have boxes of?

Natasha Lyonne, Maya Rudolph, and all of the girls like Gisele [Bündchen], all of the models.

What prompted you to start going through all of these photos of Winona?

I first talked about it with Sofia [Coppola] a long time ago. Then I started collecting them, because they were everywhere, and I had to put them in one area. I kept seeing IDEA Books posting [photos of Winona], and I have their “Winona” shirt and sweatshirt. So, I DM’d them and said, “You do all of these Winona things, and I have pictures of her from the last 20 years. Would you be interested in doing a book?” And they said yes. Then it became more than that when I started working with Francesca Sorrenti.

With such an expansive archive, what was the editing process like?

I just start out with everything. I buy a lot of books, so I know what I want my book to look like. Then I have somebody with a fresh eye, like Francesca, look, and I can say ‘I’d rather this one’ or ‘She looks so beautiful here.’ It’s really hard because then she’ll see something beautiful, and I’ll say, ‘That’s not my favorite, this is my favorite.’ I pretty much have everything that I love in it.

Winona is such a private person. Were you at all nervous to include some of the more intimate photos?

Of course I was nervous. But I had her blessing and she was so excited about it. It wasn’t like a tell-all. It’s just pictures and there’s still such a mystery there.

Talk to me about your friendship with Winona. What kind of things did you do together?

We had sleepovers. We would go to premieres together. We went to the Met Gala. She was my date one year when Marc [Jacobs] hosted with Kate Moss. I went to Jimmy Fallon with her. We just have fun together.

Do you have a favorite memory with her?

The Met Gala was probably my favorite. That was, I mean, beyond. I had never been to the Met Gala before. Marc and Kate were the hosts. I remember when we got to the top of the steps, watching all the famous men look at her. They all loved her. I was watching all their faces. She’s gorgeous. It’s like every man’s dream—and I had her.

I want to talk about some of the tabloid and paparazzi clippings of you and Winona that you included in the book, with headlines like: “Winona’s Shopping, Interrupted.” Clearly you two have a sense of humor.

She has the best sense of humor. There’s a funny story for one of those. My dad saw this in Pennsylvania in the Post, and he’s like, “Robert! You’re in the Post!” So I ran out to buy the Post, and I’m like, “I’m not in the Post.” I checked every page. It was only in the New Jersey edition! So my dad had to go to New Jersey to get these copies. We didn’t even know somebody was taking our picture that day.

Do you have a “Free Winona” shirt?

Of course I do. I have every color!

There are so many photos of Winona in your office. Clearly you all had some fun times down there. Do you have a favorite memory from the basement at the Marc Jacobs store?

I think the day with Winona and Kate [Moss] and Patricia [Taylor], Keanu [Reeves]’s mother. We were there the whole day. Marc came to visit. There were a million paparazzi outside waiting, and they didn’t come out until very late in the day. Kate was cutting gowns on Winona and making them into minidresses. It was so much fun.

I can’t imagine taking a bad photo of Winona. But as her close personal confidant, did you ever let her know if a dress or look wasn’t working?

No, she knows. You don’t tell Winona Ryder what looks good. She knows. You don’t tell Kate Moss or Sofia Coppola what looks good on them. They can pick something that I hate on a rack, put it on, and—oh, my God—it’s my favorite dress. That’s amazing, when something you hated becomes your favorite thing because somebody put it on the right way. Winona loves to make things her own. She would cut the strap off a bag and put her own strap with guitar pins on it.

Did you ever get emotional going through the photos while working on the book?

I did when I took the pictures. The first pictures I took of anybody, that was emotional. Like, I got it! Waiting for it to develop in my back pocket, it would be a surprise later. Then it would be a treasure.

You and Winona have been friends for over 20 years. What is the secret to a long-lasting friendship?

Trust.

After all these years, has Winona ever talked to you about starting her own Instagram account?

No, I don’t think she’s that type of girl, which is the reason why I love her.