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Cheryl Hines’ path to the director’s chair is as far from conventional as you can get. She couldn’t even afford to train with the improvisational troupe, The Groundlings. For her birthday, her friends and the regulars at the bar she was working at, chipped in and paid for her very first class. A short while later, Hines auditioned for the show that would make her a household name, Curb Your Enthusiasm.

Just as unlikely is her transition from actress to director. Well, actually, there wasn’t much of a transition. Hoping to find someone who understood the tone of the late Adrienne Shelly’s writing, Shelly’s husband and Serious Moonlight producer, Andy Ostroy, and his co-producer Michael Roy decided to offer the directorial gig to Hines. With zero feature film directing experience under her belt, Hines was not only taken aback, but confused. Once the dust settled and she absorbed the opportunity at hand, Hines knew she had to direct Serious Moonlight.

How’d you balance making the film you wanted to make and still respecting what Adrienne Shelly might have wanted?
I really love the way Adrienne wrote. She was a great writer and I felt like the only thing I could do was to, to tell the story the way I saw it and to do the best job I could do telling that story. So, I decided early on in the process I can’t approach this film with what would Adrienne have done, how would she have wanted it to be because you’ll never know, then you’ll always be second guessing yourself. I just tried to find all the comedy in the script as much as I could cause I thought she was such a funny writer and bring that to the screen.

How closely did you stick to the original script?
I stayed very close to the original script. That was one of the ideas going into making this film is that Andy really wanted to keep the script as written by Adrienne. That being said, there were things that we did change, but changes didn’t come easily and they were talked out and thought through. One of the big changes that we made, actually, was Justin Long’s character – was written that he comes up mowing the lawn with a ski mask on and that he had a ski mask on throughout the film. And when I read it I just felt like, I just felt like it would be more interesting to see him a little bit and to not send up a red flag already when you see a guy pulling up on a lawnmower in a ski mask, it’s a little alarming. So, I wanted to let there be a few moments where the audience feels like ‘Okay, this might be a good thing that this guys is here.’ And so we had a long discussion, I had a long discussion with Andy and with Michael and we talked through different ideas, what would work, what wouldn’t work and decided on the bandana and I asked Justin to let his hair grow shaggy and tried to make him scruffy and then give him a tattoo on his neck so as an audience member, you know who that is when you see him again.

How’d you go about casting Meg Ryan and Timothy Hutton?
I just decided, we might as well go for the gold. Might as well start big in the casting process so we sent the script to Tim and Meg just to see if, maybe, they like the script and they did. And I love Tim because, in this film, his character has to make this turn and has to really do a 180 and we see it in his face and what, you know, in this monologue that he has and I felt like Tim was the perfect person to do that because he’s so, you know, he’s such a gifted actor and he gets comedy and you believe that these two women would be in love with him. He’s cute. So he had all of those elements I was hoping Ian would have and he read the script and really liked it, called him on the phone and had some conversations with him and he said yes and then Meg – same thing! Sent her the script and she really responded to the story and to the role of Louise and talked to her on the phone. It was the first time I had met her and it was over the phone. Although we sort of travel in the same circles of people. You know, she knows Larry [David] and we have friends in common so I felt like I knew her but I didn’t. But we talked a lot on the phone and I convinced her to do this film, to take a chance we me as a first-time director.

Did you do any preparation for your first directing gig?
Interestingly enough, from the time I said yes to taking on this job as a director to the time we started pre-production, it was literally two or three months. It’s funny to think about now! [Laughs] So during that time I did as much as could to prepare. I sat down and I talked to my director friends and asked them for advice, very specific advice to this film and the challenges that I’d face with this film. Even on the set, I’d be texting questions on the way to the set I would call one of my friends and say ‘What do I do in this situation?’

Did you ever think about starring in the movie too?
Well, it’s funny because when I first got the call to say that Adrienne had written this film and they told me what it was about and I said, ‘Are you asking me to be in it?’ And they said, ‘No.’ They said, ‘We’re asking you if you’re interested in directing it.’ Then I said, ‘But, be in it?’ No! It took a long time to understand, okay, that’s not what you’re being asked right now. So, no, it was never really discussed because, because I had to make the decision of if I wanted to be considered to be a director or not. And, who knows – I don’t know, just the way things worked out. It was never a consideration to star in it and direct. I knew I wouldn’t be capable of doing that.

How did your Groundlings training help on set?
My Groundlings background is very helpful because we studied improv, as much as you can study improv. I found it to be very helpful when you’re on the set as a director to be able to go with what’s happening at the moment because something is always going wrong, at every moment you’re shooting. A lot of it you can’t prepare for, you don’t know what’s going to happen and you have to just go to plan B quickly and move on, and go to Plan C and move on. With improv, you know that’s the basic idea, you don’t know what’s going to happen next and you embrace that idea. You don’t know what’s going to happen next but it’s going to be great. And if it’s not great, the moment after will be great.

How do you bring the comedy out of such a serious topic?
It’s all in Adrienne’s writing. She was good at writing serious stories but finding funny moments in it. One of my favorite lines in this film is when she has Tim tied up and she’s walking around and she’s saying ‘I don’t want to live without you. I would rather -’ and he said, ‘Die Louise? Would you rather die?’ And she says, ‘Let’s just say I’d rather go to jail.’

What was the biggest surprise about being behind the camera rather than in front of fit?
The biggest surprise was all of the unexpected challenges. This is what we say, I’m sure that a lot of people do, but at some point in your life you change the word from problem to challenge. You can’t on the set say ‘We’ve got a problem.’ You say, ‘We’re looking at a challenge right now.’ We shot this film so quickly and everyday we’d work we start shooting I would think, ‘Nothing can go wrong tomorrow. If anything goes wrong we’re not going to make our day, we’re not going to make the film, there’s no room for error.’ And then, you know, six o’clock in the morning there’s already – something’s wrong! Somebody’s late to work or the flowers didn’t come in or somebody took home one of the props or whatever it is. It is at every turn, you know, somebody’s zipper is broken and we can’t work until they get the zipper fixed. I learned to embrace the challenges and try not to spend too much time worrying about what can go wrong. I got to the point where I’d really – when I got home at night I would put my head down and think, what if my appendix bursts tomorrow? Or what if Meg’s appendix bursts? Does she still have her appendix? Maybe I should find out if they all have their appendix. Then you start going, if mine burst probably Michael Roy, our producer, could take over but if Meg’s bursts or Tim’s bursts could we shoot around it? By the end of the shoot, I got to the point that, you know what, if my appendix bursts, it’ll be fine! Life will go on, everybody’s going to wake up tomorrow, it’s fine.

So would you want to direct again?
[Laughs] After all that, you’re like ‘You wouldn’t do that again, would you?’ You know what? I think I would. I would like to do it again. If you would have asked me that while I was shooting, I would have said there’s no way I would do this again. It’s not worth it. My hair is falling out, my skin – I had adult acne for the first time ever, I mean, I was a mess. BUT, by the end of the shoot, like you said, I got to a point where I knew what to worry about and what to let go and, you know, you learn – the thing that I learned as a first time director, I learned that pre-production conversations that you have with people – we’ll all sit around this [long, tan, rectangular] table and say ‘We’re going to get a table just like this for the scene. Everybody on board? You’re going to be the person to buy this table. You’re going to sand it and make sure’ - then you get to the set and it’s a black tiny round table. It’s like, remember what we talked about? It’s like, yeah we couldn’t get it. This other one was free or whatever it was, so I know now, okay, as a director, even though we all were here and talked about it, still I need to see the table, I need to sit down in a chair, make sure the chair works. I want to make sure you can put something on the table. We had a TV that Justin Long is supposed to pick up and steal. It’s in the script! He picks up the TV and steals it. We talked about how big the TV should be. We get to the set, we’re shooting and the thing is so heavy he can’t pick it up. It was like made of, I don’t know what it was made of, titanium. Although, isn’t titanium light? I know, I think of the golf clubs and that actually would have been a good idea. It was made of lead, okay! I don’t know what this thing was made of but no one person could pick it up and so it was a lesson. I learned a lesson at every turn. So then we had to shoot it to make it look like he was just about to pick it up and the cut away. But it worked.
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