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?
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.