FORTUNE — Donna Gigliotti’s career turns any aspiring producer’s face green with envy. Her Hollywood run began as Martin Scosese’s assistant on Raging Bull. Gigliotti’s since had stints at United Artists, Orion Classics, Miramax, USA Films, and The Weinstein Company. Her resume boasts two Oscar nominations (The Reader and Silver Linings Playbook) and one Oscar win (Shakespeare in Love), making Gigliotti one of only eight female producers with an Academy Award. She’s also had just four bosses during her 36 years in film: Scorsese, of course, and Hollywood heavyweights Arthur Krim, Barry Diller, and Harvey Weinstein.
This year, Gigliotti decided to end her streak of working for powerful men. She became president of Levantine Films in February, leaving her gig as president of production at The Weinstein Company earlier this year to instead focus on creating movies for under-served markets with budgets in the $15-30 million range. First up? Big Stone Gap, a tale of a small town spinster who searches for answers after her mother’s death—only to end up in her own backyard. Much like the audience it hopes to attract, the film is packed with females. It stars Ashley Judd, Whoopi Goldberg, and Jenna Elfman – and it’s based on the novel by Adriana Trigiani (who also wrote the film’s script).
In an interview with Fortune, Gigliotti talks about how she navigated Hollywood’s famously sexist ranks, the dearth of females behind the cameras, and why she’s banking so heavily on a female audience for Levantine’s future success.
At what point in your career did you realize you were one of the only women in the room?
I was just out of school. I had written lots of letters because I didn’t really know anybody in the movie business. There was a man at Paramount who said I could come in for an interview.
I was 21-years-old and I went to the Gulf and Western building on Columbus Circle [in Manhattan]. This guy was clearly going out the door to lunch. He said, “How can I help you kid?” and I said, innocently, “I want to be in the movie business.” And he said to me – I remember this like it was yesterday – he said, “You either have to know somebody or sleep with somebody.” That’s what he told me. And I thought, “Okay. I guess it’s time to leave this office.”
I don’t think he was proposing sleeping with me. He was just telling me how it was. And I thought, “To hell with you.” I have this deep belief that merit will out. So I knew I was just going to find another way.
What was that other way?
It was 1977 and there were only three directors I wanted to work for: Francis Coppola, Robert Altman, and Martin Scorsese. That was my short list. I wrote a letter to Altman, he never responded. I went to see Apocalypse Now and realized that Francis had gone a little off the rails at that point. So now I’m down to one guy.
It is a combination of luck and chutzpah how this happens. I literally, literally bumped into Robert De Niro on the streets of New York. Rather than saying, “Oh my goodness, you’re a movie star. You’re Robert De Niro,” I said, “Oh my goodness, you know Martin Scorsese.” I took the Styrofoam cup I was holding and I wrote my phone number on it. I said, “This is all I want in the world – to work for Martin Scorsese.” Really, Bob is my angel, because Marty had just moved back to New York and he needed an assistant.
One day I got this phone call from a man who said, “Can you come in and meet Martin Scorsese?” So I went in to meet Marty and I said, “There are two things in this world I really want. One is a Cartier watch and the other is to work for you, not necessarily in that order.” And that was my first job in the movie business.
It was luck and chutzpah. You need those two things to make it in the movie business. I need them still today.
It sounds like you know how to hold your own in a room full of guys. Where did that confidence come from?
I get down on my knees and I thank my mother every single day. She taught me that I could do absolutely anything I wanted to. She believed that and instilled that in me.
Is there ever a time when I feel the need to fake it? No. In fact, the reverse. If there are times when I feel like I’m going to cry, I simply cry. It’s just easier. Women who own who they are can simply be powerful.
And that is true, I think, in movies as well. It can be comedy or drama, but that’s what interests me and I think that’s what women respond to because I think that’s what all women really want to do: Own who they are.
There’s a lot of forces that conspire to tell them not to do that. But women are a really powerful force in culture. And what I find interesting is that Hollywood, which ultimately is run by men, doesn’t yet believe that women want to go and see movies with strong women characters.
Why is that?
They’re dinosaurs behind desks, for one thing. It is fundamentally a sexist place. You have big corporations that fundamentally run [Hollywood]. Sony Japan (ADR) is running Sony. Comcast (CMCSA) is running Universal. They want all four quadrants (men, women, and under and over the age or 25) to go see their movies because on paper that makes sense. It’s a business strategy – it’s one that is a little risky insofar as in order to do that you’ve got to make movies that are really expensive. It’s a lot of money to risk, but it seems to be a prevailing wisdom in Hollywood.
It doesn’t matter that there is actual, factual evidence that says that movies that star women—or pass the Bechdel test—are financially successful. They’re made for lower budgets and their return on the dollar is higher than movies that don’t pass the Bechdel test. Simple.
And you know what that test is? That test is hilarious. Two named female characters that have a conversation that’s not about men. That’s it.
And yet it’s surprising how many movies don’t pass that test.
Exactly. I think that test is hilarious, but it’s also shocking when you see what the numbers are and the movies that don’t pass. For me, I think that there is money to be made in movies that actually go to what is theoretically called a niche market. And this is what Cate Blanchett was talking about when she won the Oscar [for Blue Jasmine]. She said women are not a niche. And she’s right.
I think that if you make movies about or movies that have a strong woman character at the center of them, then women will respond to them because they want to see their own experiences or some fantasy of their own experience up on the screen.
I have this funny record. Any time that I have been nominated for a Best Picture Academy Award, the leading lady in the picture has not only been nominated, but she’s won. Gwyneth Paltrow (Shakespeare in Love), Kate Winslet (The Reader), Jennifer Lawrence (Silver Linings Playbook). It’s not a tribute to me. People respond to strong women and the Academy actually responds to strong women – that’s why they won the Oscars, besides being terrific actresses.
And you see serious financial promise in these sorts of movies.
To me, there’s money to be made. In the movie business, you can’t think in an airy-fairy way, like “Wouldn’t this be good for the culture.” The other half of your brain has to kick in, just like a man. Can I make money on this?
I am notorious for being cheap when it comes to budgets. You have to balance this equation of what is it that you want to do creatively, can you see the market, and what’s the price for it. That’s the equation. And that’s totally different than what Hollywood does. What Hollywood is doing is saying we want to reach all four quadrants, so they’re saying we want to reach all four quadrants and we will spend as much money as it takes to get there. I’m saying I’m happy with one – and if I get two, thrilling.
The Hollywood Reporter featured 34 ‘legendary’ producers—including you—for its pre-Oscar coverage this year. Only seven of the 34 producers were women. Is it a lack of confidence that’s holding women back from excelling behind the camera, or is it something else?
In the movie business, you have to break it down in terms of the jobs. You have to factor in that women—if they want to get married, have children, and raise families—there are limits as to what job they can do in the movie business, unless they are totally willing to ditch their kids and leave them at home. Producers and directors have to go on the road, wherever their film is located. You have to essentially drop everything. I think that that’s a large part of it. The same is true for actresses. I think that women moving further into the film business – it’s about making choices. That’s what it feels like to me.
The other thing is that you do have to function in a fairly aggressive fashion. There are times when I could be a little softer – or people would expect me to be a little softer. But I think, Ari Emmanuel [a notoriously strong-willed Hollywood agent] isn’t going to be any softer than this. If he’s gonna yell, then I have to yell.
You’ve only had four bosses your whole life: Martin Scorsese, Barry Diller, Arthur Krim, and Harvey Weinstein. What was it like working with such high-powered men?
I have been blessed – and those are not easy personalities, by the way—to work with men who just want you to get the job done. Arthur didn’t care if you were a woman, a man, a Martian, if you were green or blue. He just wanted you to get the job done. And that’s true of all four bosses I have had in my life.
And despite your bosses’ manly personas, you gravitated toward films that targeted women. When did you start consciously looking for those sorts of scripts?
It’s definitely when I was at Miramax, and then later at The Weinstein Company. Contrary to his appearance, and I can say this because I’ve said this to his face – beneath Harvey Weinstein’s gruff male exterior lurks the heart of a 45-year-old woman. It is true that his instinct is very similar to mine in terms of going after that market and that audience.
I’m sure that he does it for two reasons; the same two reasons I do it. One is that he understands that [women] is an underserved market. And the second is that he understands that financially, it’s good business.
You took a leap in March and left The Weinstein Company to become president of Levantine Films. Talk to me about that move.
The truth is that controlling your own fate is certainly appealing creatively, but more importantly, controlling your own financial fate is appealing. There are lots of people who can go and make movies at studios, but you don’t have as big a financial participation. What I’m saying is it’s really hard to make money. I just thought to myself, well why not go off and try and do this independently.
What’s your advice for young women who are interested in going to Hollywood and—more specifically—becoming producers?
I would say become a dentist. That is my honest reaction. It’s a really hard business. You have to know what you’re walking into. You need to be smart, you need to be gutsy, you need to be aggressive. You need to never take no for an answer.
And does the attitude that existed when you first started (that you either had to know someone or sleep with someone to get a job in Hollywood) still exist?
I don’t know if it still exists or not. Nobody wants to sleep with me—I’m old. But if you’re smart and have good ideas, you can work your way up.