The Winona Ryder Experience


Again, with all of my stories, there will be no mud-flinging. It’s unbecoming. At least publicly!


David Wain, the co-creator of the improv group “The State” (formerly “Stella”) as seen on MTV and later CBS, had produced his first film. It was a college cult classic titled, “Wet, Hot, American Summer” with a cast of unknowns that are A-celebrities today…



A few years later, Winona Ryder was plastered across every medium for shoplifting. A year after that, she decided to make a quiet come back doing small roles in small but unique films. One being David’s next film, The Ten, referring to ten comedy vignettes based on the Ten Commandments. Winona’s commandment? “Thou Shall Not Steal,” of course.

I remember going in for a costume fitting a few weeks prior to shooting. Winona and I were scheduled the same time. I was told she was in the wardrobe dressing area and she wanted to meet me. She was extremely cute and petite. No entourage, just chatting it up with the dresser. Girl talk.

Like most show people, she wasn’t inhibited to change clothes wherever it was required or available. She came over to meet me half dressed and we shook hands while alterations were being made to her clothing. She finished dressing and we chatted about where we lived, what job we had just arrived from, and the usual getting to know you, small talk before I made my exit. Once shooting began, I experienced a taste of the amazing Winona Ryder phenomena.

First and foremost, the paparazzi were everywhere. When we were outside, it was extremely disruptive. Legally, they had to remain behind an invisible line just behind production. Bobbing up and down, back and forth around the crew and equipment, snapping away at her every move.

I felt bad. Many of us felt almost protective of her… I know I did.  In fact, between takes, I’d casually stand to her left or right side, directly in the line of their shot. The paparazzi would yell, threatening to make it harder for us to work if we kept “pulling that kind of nonsense.”

Winona had an amazing ability to break character, ask a question of the director, then “turn it back on,” returning immediately to the scene. On/off, on/off. I can’t say the crying or scenes requiring hysterics were deep, gut wrenching, or rich per se, but 1) that wasn’t this genre; 2) she was still full out; and 3) what the fuck did I know? It was clear she knew film acting; angles, performance levels, matching emotionally what was needed for the camera and what wasn’t.

In between takes she’d step outside and smoke alone. By day two I’d go hang with her and bum one.

We had just finished a scene with a surreal rehearsal involving her, David Wain, and me standing around a bed actually discussing the best way for her to, and I quote, “fuck a dummy.”

Winona had to simulate sex with a puppet. “I’ll do whatever you want but I don’t wanna be ‘the man’.” Of course she was referring to her physical positioning and remaining visually in the feminine role. I thought that was a fascinating insight for protecting herself and her brand.

She and I chatted one on one quite a bit over the next week or so. Unsolicited, she was very forthcoming about boyfriends, about acting, about her family. I thought it was fascinating that she never owned a computer. She just didn’t want to be subjected to anything written about her.

By the last days of shooting, she’d hang on me like a bud. We’d hug goodnight. The last day together she took me aside and congratulated me on my first film, telling me I was a very good actor. She was probably just being nice, but it was something she didn’t have to say.
I only recall one afternoon of diva-like inklings. I think she just needed to remind herself or the producers of who needed to be treated special. Again, this book isn’t a public mudslinger. You’ll have to call me to hear what took place.

At one point she and I took a walk through the neighborhood. Even in a supermarket, the flip phones were up all around her. Awful. It’s no wonder some celebs can get socially awkward. As we walked down the street, the paparazzi were literally five feet in front of us walking backwards. I’d joke, “Come on guys, can’t I get a moment’s peace?” One of the men asked for her autograph. Knowing these guys sell the signatures on Ebay, she apologized and explained that she only signs for children. One of them cursed her out right to her face!

Half a year later the film went to Sundance. The night of the first viewing and Q&A session, she walked into the green room, saw me, ran over and gave me a huge hug. We exchanged pleasantries and she told me her father loved my comedy DVD that I gave her so much that he watched it once a week.

A highlight was when she, my brother, and I were at a cocktail hour. She grabbed my arm and said, “Come here. I want to introduce you to my friend Tony.” I turned around. It’s Anthony Hopkins. What the hell am I gonna say to Anthony Hopkins? (No — nothing about fava beans. I know you were thinking it.) We ended up chatting about his directorial debut at the festival. He was extremely charming and engaging.

Later that month I was going to play a club in the west village near her New York apartment. I asked her if she wanted to go. She replied, “Really? I’ve never been to a comedy club before!” Someone in their 30s has never been to a comedy club? Some lead — well, just a different life. I have met so many star actors that play roles of common people doing common things that they themselves have never experienced due to their celebrity bubble.

Winona and I did not stay in touch. I discovered that for most actors, you bond during a project, and then that’s it. You are rarely if ever pen pals. You just add it to your book and move on to the next experience.

Now what happened to my wallet?


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