Winona Ryder’s new illustrated book contains about 100 previously unpublished photos of one of her best friends

July 15, 2024

Robert Rich met Winona Ryder shortly after the release of Girl, Interrupted in 1999 while she was shopping at the Marc Jacobs store in the Mercer Hotel in New York City. Rich, who was the designer’s communications director at the time, nervously approached the actress.

“I said, ‘I love ‘Girl, Interrupted,’ and she said, ‘It’s a chick flick,'” Rich recalls. “I said, ‘I’m more of a chick flick guy.'”

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They became fast friends. Now, more than two decades later, Rich is the author of Winona, a coffee table book with over 100 photos by Ryder and a foreword by Jacobs. Rich took most of the photos. These are not glamour photos, but intimate Polaroids and images taken in private moments together – many of which were taken in the offices of Marc Jacobs with other superstars like Kate Moss.

diversity met Rich via Zoom as he prepares to host a book launch event in New York City on Thursday at Dover Street Market in New York.

How many photos of Winona do you have?

Tons! Tons! First it was Polaroids in the office. I knew Winona before there were camera phones, so that was forgotten when we had camera phones. There are old phones that I never downloaded the photos from, so we found a lot of photos on those too. I could make 10 more books of Winona.

Winona is very reserved. Did you have to present the idea for the book to her and convince her to let you write it?

I simply texted her the idea and she loved it.

What are your favorite photos in the book?

Brian Bowen Smith took nude photos of Winona that we did for the Protect the Skin campaign against skin cancer. I begged her and she was like, “I’m not taking my clothes off!” But it was just me, her and Brian. It was very private and she did it. It was a lot of fun and they’re probably my favorite photos.

When did you realize that you and Winona had become real friends?

I don’t know, but I remember we were going to go out to dinner for Valentine’s Day. I was so excited, but it never happened! But I waited with bated breath. At some point I was in LA a lot for work, doing fashion shows at the Beverly Hills Hotel and the Chateau, and she always came to all my things. Slowly it developed into a friendship.

Winona was caught shoplifting a Marc Jacobs shirt from a Beverly Hills department store in 2001. How did you react when you first heard this news?

I’m not sure. Maybe I laughed.

And she did. In her book we see her wearing the now iconic “Free Winona” t-shirt.

I have this t-shirt in every color.

What is the biggest misconception about Winona?

People don’t know how funny she really is. She’s really funny. She’s such a sweetheart.

What is the best gift you have ever received from Winona?

My favorite number is five. One day she came into the store with a cashmere sweater with the number five on it. I said, “That’s my favorite number.” She took it off and gave me the sweater. I still have it. I wish it would fit me. Maybe I can lose 35 pounds with Ozempic.

What will be your next book?

I think a book about everyone who has walked through the office would be interesting. I have pictures of Selma Blair. I can do a book about Natasha Lyonne. I could do one about Kate Moss, Jared Leto, Sofia Coppola, Gerard Butler.

Gerard Butler?!

He was friends with a makeup artist I knew. She always brought him to our place and we became friends.

These questions and answers have been edited for length and clarity.