Sideways marks what many consider a comeback for Thomas Haden Church and Virginia Madsen. Church was almost considering retiring from acting after several of his films went straight to video. Madsen also found many of her films losing theatrical distribution. Neither of them mind the term "comeback" despite the connotations that they had some failure to come back from.

"Sideways is the only movie I met on last year to act in," Church said. "I've really started moving more towards writing and directing. I had a series called Ned and Stacy that I was a producer and a writer on. And then after that show ended I had a two year deal at Disney to create and star in a series for ABC and Disney. Just kind of this glacial drift begins. It's diminishing returns and especially after you star in your own series, which I very much enjoyed being a part of on every creative level, you just start drifting toward something else. It's not something intentional. I didn't really wave goodbye to acting, but I wasn't as much of a presence. Then I moved to Texas full time three years ago. I come back to LA whenever it's necessary. But it's not I'm splitting my time between acting and ranching. It's more like writing and looking for my next directing job. And then Sideways came up. It's hard to explain. Things present themselves and either they are really cool and you want to be a part of it or you use a separate barometer which is, 'Do I need the money?' I worked in television a long time. I have financial security from 10 solid years of television. So now it's like if something cool happens, then that's great. Otherwise I'm content to just stay in Texas and wait for something cool to happen."

Madsen said, "[It]'s very flattering. They're sort of saying it's well deserved. They are kind of saying, 'Welcome back.' And also, really people haven't seen me in a feature film. I mean, the last feature film I had was Candyman. The independent films that I did never made it to theaters, and only a couple of them even made it to completion and went sort of unceremoniously straight to DVD, including James Coburn's last film."

Church plays Jack, a man on his last bachelor fling before his impending wedding. During a trip to wine country, he ends up having an affair with a woman he meets at a winery. Madsen plays that woman's friend, Maya, who ends up romancing Jack's best friend, Miles, played by Paul Giamatti. Spending the film cheating on his future wife, Church feels the film makes it clear that he's not entering into marriage for the right reason.

"As the prospect is turning into an imminent reality, he kind of has these sequences of being unnerved about it," Church said. "The reason is because as the prospect turns to reality, he's having to come into kind of honest terms with the choice that he's making, or the choice that he's already made. I think he's headed down the slaughter shoot into a fairly loveless and miserable experience. In the book, it's absolutely doomed before it even begins. I mean, Jack is like a guy who, say they are 40. We kind of left it around 40. To be really simplistic, you don't change your stripes at 40. This is a guy that has just had this immediate gratification as the compelling fuel through life. And it's just, you know, marry a girl that's the wealthy Armenian real estate magnate, it's a sideway. It really is. The prospect of marriage, which is supposed to be bountiful and hopeful, it's just really another kind of tangential thing in his life."

Jack may have a lot of explaining to do when he gets home, but on the set of the movie, Church found himself in the middle of an awkward marital situation. He was shooting sex scenes with the director's wife, Sandra Oh. "You know, he attempted to put me at ease about that from day one. And then Sandra was very sweet about it. Wasn't it John Huston's character in Chinatown who said, 'You never know what you're capable of until the circumstances prevail, and then you're capable of doing anything?' It's one of those scenarios where no, I never imagined that I'd be directed in a love scene. Not even a love scene because it's kind of a hard-core sex scene because it's kind of just purely played for this carnal venting. At first Sandra and I are like, 'Let's make it funny because that's safe.' Then he just kept pushing us to make it more real and more sensuous. One of the takes he used is somewhere in the middle. I really don't know which one. Alexander certainly would. But yeah, it's a little awkward. But he told me straight up when I first met with him, 'That's going to be my wife. That's going to be Sandra.' It's just one of those things. Everybody is a professional. It's just part of the story. It's just a piece of it."

Maya's relationship with Miles is more verbal than physical. With both characters coming out of difficult relationships, they each keep somewhat of a distance from each other. But when Giamatti gives a speech about wine, it turns out he's opening up his inner secrets.

"I think that was so clear in the script," Madsen said. "We know that's exactly what he's saying. I think he doesn't but Maya does. That's what does it for her. That's just beautiful what he's saying. He is that delicate man and I think she really likes that a lot. There are some of us who like nice guys. There's a lot of us actually that like nice guys. And after being with probably a really complicated man who was kind of mean when she was married, probably not a really nice man that she was with when she was married for many years - and she gave her youth to that marriage - it's really hard to bounce back from that. That's not what she would look for again. She's known Miles. She's watched him for a long time as acquaintances so this is exactly the kind of man she would choose."

In a movie about wine, you couldn't have the actors drinking real wine. For Church, grape juice was just no substitute. "I would say 95% of the time, because you just can't remember your lines if you're drinking alcohol, I would say about 95% of the time it was grape juice or this fake wine, which was horrible. It's like they make it and then they extract the alcohol. It's really terrible. But the grape juice has such a high sugary content it starts giving you gastro-intestinal fits and then you're asking for anything else. We would, late at night every now and then, Alexander would want to open some wine for the cast and crew just as a reward for a good day's work."

Madsen found the film's wine content educational. "All joking aside, it was a great experience," she said. "And then I also began to learn about the history of the area and how old some of the vines are, and how it all started. Because I'm Danish I knew about the history of the Danes coming here and the cows, and everything was about cows and dairies. There were some vineyards that started more in the Santa Barbara area. But out there [in Santa Ynez], mostly really when it comes down to it, it starts out with a couple of hippies who really don't want to be in society anymore. And they're like, 'You're planting what now?' 'Dude, now we're going to make our own wine. Nice…' So that's how it got started, I think."