Virginia Madsen Reflects on Portraying Maya in ‘Sideways’

I was lucky enough to attend an anniversary screening of Alexander Payne’s “Sideways” at Laemmle’s Monica Film Center in Santa Monica, California. I remember and watching and loving this film back when it was released back in 2004, and now it has reached its twentieth anniversary which just scares the hell out of me. This screening was followed by a Q&A with some of the film’s participants as well as the authors of the recently released book “Sideways Uncorked,” Kirk Honeycutt and Mira Advani Honeycutt.

But make no mistake, the real star of the evening was Virginia Madsen whom everyone who loves “Sideways” was truly thrilled to see. She portrayed Maya, the divorced waitress who captures the attention of the ambitious but very depressed Miles (Paul Giamatti), a writer who just might be about to publish his novel for the world to see. Madsen deservedly earned an Oscar nomination for Best Supporting Actress for her unforgettable performance here. Cate Blanchett ended up winning it that year for her work in “The Aviator,” but there is no forgetting what Madsen did, especially after Maya’s speech about her love of wine.
Before “Sideways,” Madsen was best known for her work in movies like “Candyman,” “Electric Dreams,” “The Prophecy” and “The Rainmaker.” Around the time it came to audition for this now classic film, Madsen openly admitted her career was not doing well and that the odds were against her in playing Maya.
Virginia Madsen: There was talk about getting someone who had a bigger name, but I got the audition and I was working with a coach, so I was really, really ready. They weren’t giving us the whole script though, and then I said, well, can I just have a couple of more scenes, and they just sounded like me.
In addition, she was very familiar with the Santa Inez valley and the other areas which “Sideways” takes place in as she considers them her weekend getaway. Also, this film marked the first time Payne made a film outside of Omaha, Nebraska.
Virgina Madsen: I lived about an hour from there. I didn’t ever go wine tasting. I just went there to sort of be a hippie and climb trees and have this beautiful sense of serenity, so I knew what I felt like when I was in the valley. So, I just went to play myself.
And we can all agree that Madsen’s greatest scene in “Sideways” was when she talks to Miles about her love of wine as it seduces us every bit as much as it seduces Miles. As a result, this made her meeting with Paul Giamatti all the more agonizing.
Virginia Madsen: I loved the part where I talked about wine in that scene with Paul, so I just got this one chance in the room with him. So, I said I just love this screenplay, I love this role, and I love when she talks about the life of wine. I went into the monologue, which you were not supposed to do for the audition. He went, “would you like to do the monologue?” I said, “Yes, sure.” I was so prepared. The tone in the writing changes in that scene. And when it was over, we just looked at the casting director and he said, “You know, we should have everyone do that monologue!” He (Giamatti) wanted me, but it took a while to hear a yes. I knew who Paul was as an actor, and I knew we would have chemistry. I am never wrong about that.
Then there came the time when Madsen met up with Payne about “Sideways,” and he offered her the role of Maya at the Chateau Marmont, something any actor or actress loves to be given the role of a lifetime at. But this also resulted in something actors might be reluctant to agree to.
Virginia Madsen: We met at the Chateau Marmont, and he said, “I want to ask you, would you do me the honor of playing Maya in my film ‘Sideways?’ And I was like, “Oh, well.” And he said, “I have one request though, are you willing to do this movie without makeup?” And I said, “Well Alexander, I’m not wearing makeup now, and that’s what I mostly do.” I did that in three films before that, and the greatest thing about that is you don’t have to get up quite so early. The only request I made back to him was, as long as I can wear mascara and some lip gloss on the date because, if a woman goes on a date, she’s just gonna do a little something, and he agreed to that. It seems to be nowadays more than ever this effort to make people look real, and they kind of look like hell, and that’s also distracting.
After all these years, “Sideways” has lost none of its power to entertain, be it in comedic or dramatic ways. Some films are quickly undone by time, but this one never will as everyone can relate to it and its characters in various ways. And when it comes to Madsen’s performance, she will make you fall in love with Maya every single time.

