Winona Ryder in Sex and Death 101 Courtesy of Anchor Bay Entertainment

Unfortunately, we had the least closed sets ever. It's so painfully embarrassing. Since I was rushed for time, I ended up having to shoot with 2 cameras. So Winona, she's very briefly [topless]. If you have a freeze frame you can see her breast [in a] scene at the end where she kisses Simon. But she was very open [about] rehearsing without her clothes on. Then I brought the whole crew in, and she was very funny, she was like Mrs. Roper from Three's Company, complaining that she hadn't had a date in a while and everybody's too shocked to actually laugh but we have strained smiles on our face. But that day [we] kept poor little Winona Ryder topless, and I look around and it's like, "How did I get 2 boom guys? Who's that park ranger holding a wire that's not plugged into anything?" I felt a little embarrassed but she was very cool about it.

Can you talk about some of the sets and stylization of the film, particularly Swallows restaurant? And the more noirish femme fatale sequences?
Well, first of all, I feel like the producer color timed the film 2 points too bright for my liking, but that's another story. The fact that he is going through these different women and different stages of his odyssey allowed me to change up the look and change up the lighting. I think my opening credits go on a little too long, I know, but I just wanted to get people [to realize], "OK, this isn't Good Luck Chuck, this isn't your usual kind of sex comedy." Again, we'll see if it's to my discredit, but I felt like I had so many different influences that this is a premise that allowed me to do different things.

There's a vision of Winona's character becoming her own prince charming, and she takes on the feminist role of making men shake in their boots, but then it ends with a scene that recalls Romeo and Juliet. It's a nice ending; there are different paradigms working.
I guess [I'm saying] some strange things about marriage. To me, having the happy ending is almost subversive; the perfect marriage is 2 jagged, broken people whose parts fit together. If the marriage is too happy, just like "I'm in love with you, I'm in love with you," that there's something weird, there's got to be a crack. To me the perfect marriage is 2 people that are crying. I think a good couple is [two people who have] had their hearts broken but they've also broken people's hearts.

You've also got to be open enough to really commit to something.
Yeah. 'Cause obviously Eliot Spitzer should have had sex with like at least 10 more women before he got married.

Why such a long break from directing? Are we going to see more of you behind the camera? Any plans to co-direct with your brother [Mean Girls director Mark Waters]? Do you guys consult with each other while working on your own projects?
I definitely have some projects going with my more commercially successful younger brother. He likes to remake my movies, get the money I didn't get the first time. I don't know what Sex and Death 101 Mean Girls is going to be, but I think it's [top] on my list and has 5 women and Kate Hudson's one of them. But anyway, yeah, it does take a very long time to write the completely original screenplay. And so it's funny, I have these ideas that I've had since like the late '80s but it takes me such a long [time] and perhaps the dialogue is overwritten because I've been kind of collecting dialogue since before I started writing the movie. So I think it makes the movie better in a way but... like I used to complain about Stanley Kubrick only making a movie every 10 years, [and] now I have a sense of how fast 10 years goes by, I'm like, "Geez, he was actually rushing."

MORE SEX ON FILM...
The Old Hand: Brian De Palma
The Dirty Dutchman: Paul Verhoeven
The Crossover: John Cameron Mitchell
The Punk Rebel: Larry Clark
The Big Buffalo: Vincent Gallo