Damien Oliver is fashion ambassador for The Mens Shop.
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When Damien Oliver smiles, his whole face crinkles like a piece of paper in your fist. Watching it from a metre or two away, you can’t help but smile with him. His persona shifts with the expression, from flinty jockey to someone far more human.
What’s making Oliver grin today is the art director’s command to “rip open your shirt like Superman and show us those silks!”. He’s just put on several layers of clothes for the photo shoot, including a sharp Italian suit, a French-cuffed business shirt and riding silks.
The scene takes place near the entrance to the Prince of Wales Hotel, on Acland Street, St Kilda. “Onya Damien!” a tradie in high-vis shouts from across the road. Oliver doesn’t flinch and holds his shirt open to reveal the bright-pink material underneath.
Awkward public photo shoots come with the territory in his new role as fashion ambassador for The Mens Shop, an online fashion retailer aimed at the cashed-up, time-poor gent.
The new brand about town has also enlisted Collingwood Football Club’s forward Travis Cloke, Sydney actor Firass Dirani (who appeared in the movie Killer Elite) and Charlie Pickering (co-anchor of TV show The Project).
Fashion model is a role Oliver takes on with a breezy confidence that comes as a surprise.
How are you finding this modelling caper, I ask to begin, expecting the awkward chagrin of a sportsman. “It’s a bit easier than getting on a horse,” is his lightning quip as we walk up the stairs of the Prince of Wales to the rooftop deck for yet more shots and then a sit-down. “But I think the novelty will wear off pretty quick.”
You seem to take direction pretty well, I say, referring to the good-natured spirit in which Oliver took demands from the photographer that included “now smilier!” and “seriouser!”.
“Yes I’m married, that’s why!” He’s quick on a thoroughbred and he’s quick with a comeback. We are off and racing here.
Oliver considers fashion and racing an obvious match. “Racing’s something you’ve got to dress up for and look sharp,” he says. “I think if you want to be successful in racing it’s important to look the part.”
Asked to list his closest fashion rivals off the field, Oliver namechecks a who’s who of Aussie jockeys. “A few like to think they’re up there.” Like The Weekly Review’s one-time glamour model Glen Boss? “Yeah, Bossy dresses up a bit, and Aaron Spiteri likes to think he’s a pretty snappy dresser.
“A lot of the guys ride all around the world so you get exposed to all kind of fashion styles. The French jockeys set a bit of a standard, but there’s no one else in Dettori’s class,” he says of Italian jockey Frankie Dettori, winner of more than 500 group races but loser to Oliver in the 2002 Melbourne Cup when he rode the highly fancied Pugin.
Life is unlikely to change much for Oliver with his new sponsorship, certainly not as much as it did after The Cup. But which cup are we talking about? “The movie, or the Melbourne Cup do you mean?” Let’s just go both.
“My life changed more after winning the Melbourne Cup than it did after the movie,” he says, referring to his win on Doriemus in 1995. Oliver won the “race that stops a nation” a second time on Media Puzzle in 2002, which set the scene for the movie The Cup, starring Stephen Curry as Oliver.
“All of a sudden you’re more recognisable to more people and there are more opportunities; it opens a lot of doors for you on and off the track. In comparison, I suppose the movie was quite humbling. For people to feel enough about something you’ve done in your life to make a movie about it is really humbling; there’s no other word for it.
Media Puzzle wins \ 2002 Melbourne Cup
STUART HANNAGAN/ GETTY IMAGES
“You’re hoping that it’s going to come across well and that people are going to receive it well. It was pretty true to life, but there was a bit of Hollywood in the way that they built up to the race. When you’re living through it, you’re not thinking about the drama of the situation, you’re just doing your best to make it through. The second and third time I watched it I noticed that Stephen Curry picked up on my little idiosyncrasies. He did a great job.”
There were two moments in The Cup that stood out for Racing Victoria’s international recruiter, Leigh Jordon. Seeing the Irish gelding Media Puzzle storm home was an obvious highlight: “Damien’s win has made my cause to get internationals to the Melbourne Cup easier, no doubt.”
But more moving was the scene based on the moment when Oliver, wearing his brother’s jodphurs emblazoned with “J.?Oliver”, passed the winning post on Media Puzzle and then looked up to the heavens to pay tribute to Jason, who had died only a week before in a fall at Belmont Park Racecourse in Western Australia. “My boy,” he shouted, kissing the sky. Oliver considers this part of the film “a nice legacy for me and my brother”.
Jordon calls it a “famous moment in racing history”. Aside from the sentiment, the running of the 2002 Melbourne Cup showcased Oliver’s “unique skill”. “What makes Damien Oliver great is his ability to judge the pace of the race and know where to put the horse and to know the right time to go. He seems to judge all these things to perfection. In my recruitment travels overseas you only have to mention Australian racing and the name Damien Oliver is synonymous. He’s the first jockey mentioned and he’d be considered the dominant Australian jockey for the past decade.”
Oliver has a similar take on the difference between a good jockey and a great one, but before the technical comes the animal element; the natural rapport required between human and horse. “An important part of a jockey’s job is connecting with your horse. If you’re not working together in unity you’re going to struggle to get the result you want. Over the journey riding has become a little bit more like a lifestyle and a job in some ways, but the love of horses and animals is what got me into racing before any of that.”
Asked to name the best horse he’s ever ridden, Oliver doesn’t take too long before nominating Australian thoroughbred Northerly. Would he like to ride Black Caviar? “Definitely, yeah. You don’t get too many like her.”
He says from a skill level, being a jockey is “all about making the right decisions at the right times. We’re in the business of making a lot of split-second decisions, and I suppose if you put yourself in that position enough you make the right decisions.
“You’ve got to be able to read what’s happening in a race not only at the present time but in the time ahead too,” Oliver says.
“I’ll have a picture in my mind and I’ll even have a little bit of a map of how I think a race is going to structure up. If you get into the gate with no game plan you’re really in no-man’s land. You’ve got to be able to adapt to any situation pretty quickly.”
If managing the delicate balance between instinct and rational thought is the jockey’s challenge after the gates fly open, harnessing the nervous energy leading up to that moment is the other side of the coin.
“It’s nice to have nerves because it shows that it means something to you,” Oliver says. “At the same time, you can’t let the nervous energy get the better of you and start to affect your judgment and your performance.”
For Oliver, his own supply of nervous energy is “pretty unlimited. Jockeys are adrenalin junkies. Every race is a serious adrenalin rush.”
What does Oliver do when he can’t get his racing kicks? It turns out that the concept of a “break” from racing means only one thing to an elite jockey: injuries. He thinks immediately of the 15 months off riding in 2005-06, after he broke his back in a horrific fall at Moonee Valley. It prompted surgery that included titanium rods and four screws inserted into each side of his spine and the fusing of six vertebrae.
“You’ve got to be able to read what’s happening in a race not only at the present time but in the time ahead too,” Oliver says.
Instead of going stir crazy, he took the time to “chill out and relax”. While the period of his life is remembered as a “long hard road”, he was also able to “play golf and go surfing”.
Managing nerves, pain and injuries is all a part of Oliver’s everyday life, but even more challenging is managing his appetite. He has a lunch at Lamaro’s scheduled after our interview and his concentration is starting to lapse at the thought, not helped by my line of questioning.
“You do crave things,” Oliver says, a little dreamily. “Not so much the rubbish foods, it’s more the hearty meals. As I’ve got older, my tastes have probably got a bit more extravagant. I like going to nice restaurants and I like sweet flavours and a lot of different flavours in food as well. When I can’t eat, I don’t eat a lot but when I do eat, like today for lunch, I like to eat well and eat good food.”
And with that, Oliver is as good as gone. All that stands between him and probably Lamaro’s Szechuan duck dish is me, and a quick costume change.
The interview started with Oliver layering up his clothes and it finishes with him stripping down. There are plenty of people around – stylists, photographers, assistants – but he takes his jacket, shirt and riding silks off without self-consciousness to reveal a body of solid, sculpted muscle.
He’s rocking tanned abs, pecs, biceps, the works; it’s like a Men’s Health magazine cover, just not quite to scale. You might expect a topless jockey to be gawky and malnourished, but Oliver is stone-cold ripped. It’s one final surprise for the day.
So what’s eating Damien Oliver? It’s hunger. I’d read that jockeys are obsessed with food, and it certainly seems to be his favourite topic of conversation. Keeping this in mind, and the torturous “binging and starving” cycle of the jockey that Oliver admits to being on much of the time, his strong physique is a physical manifestation of his iron will.
His physique tells of the commitment he continues to make to the sport that’s taken two of the most important men in his life from him: his father Ray in 1975 and his brother Jason in 2002 through fatal falls.
As we shake hands, I ask him if, all things considered, he feels his fate is in a way grimly tied to racing? His eyes narrow and refocus on something in the distance. For once he pauses before he responds: “I’ve felt that it has been over the years but I’m probably getting closer to the end of my career now. I’m in the home straight at least. I’ve certainly achieved more than I ever thought I would in my career. It’s given me a wonderful life and I feel very fortunate. It also makes me sad to think about racing because it’s taken my brother and my father too.”
If, metaphorically, Oliver is on a horse in the home straight, can he look around quickly? Is he winning the race?
He smiles and his whole face creases up like it did in the photo shoot: “I’d like to think I’m ahead of the pack on the home straight, yeah. I’ve been pretty successful. Hopefully there are a few more winners yet to come.”
Oliver’s eateries
At first it seems like it would fall under the rule of thumb to “never trust a skinny chef”, but according to Oliver, you should always take the culinary advice of a jockey. “We don’t get to eat much, but when we do, we make it somewhere good.” He names his top four spots in Melbourne.
Lamaros
273 Cecil Street, South Melbourne. 9690 3737
One of Melbourne’s favourite gastro pubs, Lamaros is known for its signature dish of crisp-fried Szechuan duck, but step outside the signature and try the chorizo arancini, or take your partner to share their heaped antipasto plate.
Rockpool Bar & Grill
Crown Casino, 8 Whiteman Street, South Melbourne. 8648 1900
The ponytail came and saw, and now it’s fair to say that he’s conquered. Neil Perry’s Melbourne Rockpool dominates in the briny depths, showcased by the Four Raw Tastes of the Sea dish and on terra firma with its $75 440 gram rib-eye steak. “When I have cravings it’s for a big steak,” Oliver says. Few come bigger than this one.
Nobu
Crown Casino, 8 Whiteman Street, South Melbourne.
9292 7879
Guilt-free bingeing on high-quality sushi and sashimi at Nobu is an elite jockey’s right and Oliver upholds his often. Asked to name a favourite dish, he struggles. “All of them, I’ll eat just about anything on the menu.”
Railway Club Port Melbourne
107 Raglan Street, Port Melborne. 9645 1661
Pick your own meat from the display fridge and hover annoyingly as the chef cooks it to your taste. Oliver’s steak obsession drives him here more than any other place for his fix. “It’s my little local steak place.”