Australian director Simon Wincer specializes in movies featuring big animals.  His most successful film is “Free Willy,” but his most frequent stars are horses, in films like “The Young Black Stallion,” “The Man from Snowy River,” and the fact-based “Phar Lap.”  His newest film, “The Cup,” is based on the real-life story of the 2002 Melbourne Cup, when jockey Damien Oliver, devastated by the loss of his brother, best friend, and fellow jockey Jason Oliver in a tragic racing accident, rode the Irish horse Media Puzzle, to a triumphant win.  I spoke to Wincer about working with the great Irish actor Brendan Gleeson, who plays the Irish trainer, about the real-life mother of the Olivers who supported her sons even though their father died in a racing accident, and what he wants families to learn from the film.

What were some of the challenges you faced in making this film?

Raising money to make it was one.  It took a while but they were changing the track where we were shooting the film.  I wanted to capture it as it was before it changed, so we had to shoot some of it in advance.   Then eventually when we did start production, it didn’t take all that long, although because of Brendan Gleeson’s availability—he was just available for a very short window—we ended up having to shoot the film in winter. and of course, it was Melbourne’s wettest winter I think in almost forever.  So the racing sequence had to be abandoned and shot in the spring when the tracks had dried out. It was an adventure, but it was fun.  The weather is always a challenge.  I’ve been to places in the world, as for example, in Turkey where it has never ever snowed on the Mediterranean, and of course we were shooting there and bang! Snow.  I’ve seen it in the desert where it hasn’t rained in five years and guess what happened when we arrived to make a film? We got ten inches of rain, so that tends to happen to film crews, but that’s the whole fun of it.

 It was a very big important story in the news when it happened, but what made you think it would be a great movie?

It was such an extraordinary story, the fact that the mother had been through it twice really interested me, how a woman can be so strong and put under such extraordinary stress in life. I suppose I’ve always wanted to do a film set around Australia’s biggest annual event, which is the Melbourne Cup. In Australia it’s called “the race that stops the nation” because literally everyone in the country stops—this is the Melbourne Cup and every office has a suite, everyone has a bet on.  It’s a tradition and it’s part of our culture. This year it’ll be the 152^nd Melbourne Cup, so it’s a very old tradition. It’s a public holiday and all that sort of stuff, so it’s just part of that culture, you know? And that fascinated me to build the story around that; you need a good story to do it and I felt that was the story.

Tell me more about Mrs. Oliver.  She lost her husband and her son and still wanted her other son to keep racing.

She’s a very strong lady.  She was very much part of a racing family and it was just their lives, despite the fact that it’s touted as the world’s most dangerous job. It’s highly dangerous, but it’s just in their blood. She’d seen these two little boys wanting to be like their dad and grandfather.  I think she just wanted Damien to make up his own mind whether he decided to ride or not. She’s quite an extraordinary woman. She’s quiet, but she’s very strong and very, very brilliant to go through that emotionally, which I tried to capture when she walks into the hospital to see her son, flashing back to the memory of her husband, which was exactly what she had been through pretty much. It was extraordinary. I suppose it comes from a slightly different era when values are different and she’s just one of those stoic women, just extraordinary.

I want to ask you the same question I asked the director of “Secretariat,” which is how do you make a race exciting when everyone knows the outcome?

People have said to me in Australia, “God, you know, I was on the edge of my seat, thinking that he wasn’t going to win the race, even knowing that he won the race.” I wanted, first of all, to make it real. I didn’t want it be hokey. Quite often in these horse-racing movies you see the hero horse gallop past and if you look closely, the horses are being gently held by the jockey so the hero’s horse can run past them.  I decided not to do that. Because I’m also a horse person and I’ve been riding and around horses all my life, I can certainly detect something like that, so I just wanted to keep it real.  And I wanted to capture the sound. It’s incredibly dynamic when those horses go fast; I can remember every take, the crew— many of them hadn’t been to the races in their lives—just the excitement to see these things come passed us at extraordinary racing speed and so close together. Everybody just goes, “wow.” So, I wanted to capture that on the screen.  I couldn’t change the result because there it was in history, but I just thought if we could make the staging and the filming of the race dynamic enough, people would get wrapped up in it because they’ve shared in this transformational journey before the race happens, and then they can share it and triumph when he eventually does win.  The race which we restaged is almost identical to the actual race, and I was a slave to that and wanted to do it exactly the same. It’s been viewed by so many people, I didn’t want it to get it wrong, you know?

You had quite a casting challenge, not just to cast actors to play real-life people who were well-known, but also to cast the horses. How did you cast the horses?

We looked at about 800 horses, I think, before we eventually settled. We bought 60 and leased another 40, and again, I wanted them all to match the originals.  In real life Media Puzzle wasn’t an easy horse, it was a difficult horse. Somehow of course, Damien has this incredible relationship with it, so you need to find something a bit special that’s got a bit of attitude and all that sort of stuff.  You have to have several because one could get injured, and you can only do a couple of takes a day when you’re doing the racing scenes.  Then you have to change the whole field.  So we had more than one Media Puzzle. The main one who did the close-ups with the actors was a horse called Spike.  He’s now in another show I did, playing a tribute  to a famous horse called Phar Lap, which is another movie I made a long time ago.  He’s just a wonderful horse because he just has this sort of attitude and you know, he’s a bit of a handful, but that’s what you want because they easily make wonderful trained horses.  He does the most extraordinary act in this new show and it’s quite moving because he’s just so graceful when you see him galloping into the arena in the spotlight, all on his own, no bridle and stuff like that, it’s fantastic—and that’s what you look for, you just look for something just a little bit special with the right look in the eye and that sort of stuff.

Brendan Gleeson is wonderful in the film.

Brendan is another joy, yes, he is one of the world’s greatest actors, I don’t think anybody would dispute that when you look at the body of his work which is extraordinary. When I first talked with Brendan, I was introduced to him by telephone, and I was in Australia and he was in Ireland.  He told me, “I’d just like to clear one thing up, I think that the Irish dialogue needs a little work,” and I said to Brendan, “That’s just what a Texan and an Australian think of as Irish dialogue.”  That sealed the deal, because he was concerned that he didn’t want to change a word without our go-ahead, of course, but his input was fantastic. So, I happened to have to go to Dublin, and Brendan and I were able to spend a couple of days together going through the screenplay and all these scenes and then we were able to introduce him to the real Dermot and then he was able to go down and spend some time with Dermot, just outside Dublin and really get to know a bit about a trainer’s life and boy, he’s just wonderful—I guess when you work with a great actor,  it raises everybody’s game, and it might be playing tennis with someone better than yourself and you rise to the occasion.  I can’t speak highly enough about what a nice man he is and what a pleasure to work with and what he brings to the set, not only the energy and good vibes but just great ideas.

What lesson would you like families to take away from this film?

The theme is how we choose how we to want to live.  Damien chose to do it by riding in this race. I suppose it is the drive and the human spirit.  He was so down and everyone thought he shouldn’t be doing it and he had this terrible losing streak but persistence wins through in the end.  It’s about dealing with adversity in a positive way.  I think if people are lifted up at the end, then I’ll be very satisfied because  while it’s extremely sad, it’s incredibly uplifting at the end when he rides — and that magic moment when you touch the heavens, it’s been forever etched in Sydney Australian sporting folk lore.