Born in Edmonton, Alberta, on November 19, 1967, Gary Boulanger began his riding career in Washington State and won three straight jockey titles at Longacres in Seattle, breaking Gary Stevens’ meet record with 247 wins in 1991. He also netted two riding crowns at Calder Race Course in 1994 and 1995. Boulanger returned to Canada, specifically Woodbine, in June 2000 and won 78 races, six stakes and more than $4 million in purses. He has been associated with Sovereign Award champions including Dancethruthedawn, who won the Queen’s Plate and Woodbine Oaks in 2001. Boulanger’s career appeared to be over following a 2005 spill at Gulfstream but after a brief stint as a trainer he made a remarkable comeback after an eight-year absence. Boulanger was the recipient of the 2017 Avelino Gomez Memorial Award for contributions to racing on and off the track. His career totals show 3,655 wins for purses over $82 million (USD).

Who is your favourite actor and why?

“Clint Eastwood. I actually got to meet him when I won a race on a horse that was named after him. When he was the mayor of Carmel at the time, I was riding at Stockton, and I rode a horse named Eastwood. The sire of the horse was named Dirty Harry, and the owners had to get permission from Paramount to name the horse that. When they named the horse Eastwood, they had to get Clint’s approval. And he gave it. The horse was an Appaloosa. The race was a Derby, and you had to qualify for it. I get this phone call in the jocks’ room and the voice says, ‘Are you riding a horse named Eastwood tomorrow?’ I said that I was and the person says, ‘Do you think you can win?’ I told him that I liked the horse a lot and thought I had a good shot. ‘Did you know the horse was named after me?’ I thought it was a joke. I asked, ‘Are you Clint Eastwood?’ And he said that he was and wanted to know if he should come. I thought someone was punking me, but he ends up showing up at the track, coming to the jocks’ room. So, I got to meet him, shake his hand and have a quick chat. The horse won, and he came to the winner’s circle. I had always liked him as an actor, so it’s cool to have that connection.”

Design your own jockey silks.

“They would be blue with silver or black trim. The logo would be a circle, either a black or silver ball. Blue is my favourite colour.”

If you had to write a book about your life, what would it be called?

“I think I’d go with The Comeback Kid. I had to deal with a lot of ups and downs in my career, some life-threatening injuries and other serious ones too. So, I think that title would be appropriate.”

Most embarrassing moment as a jockey?

“I’m pretty hardcore, so it’s tough to think of a particular moment. I used to be really shy, just talking to people was tough. I think if I was to look at something embarrassing, it would be learning about public speaking. When I first started doing well, I was in Seattle, and when I would do interviews, I’d turn red. I was really shy and not forward. That was my biggest embarrassment, that I was so nervous around people early on in my career. The Clerk of Scales in Seattle, his son worked for Boeing. He prepared CEOs for presentations. He told me that I had to get used to speaking in public, so I went to his house for a BBQ and met him. He gave me a simple exercise. He said to go to a stoplight, stop, look left, look right, and the first person I see, stare at them until they look at you, and when they look at you, don’t turn away and smile. A big fear is when people look at you, that you turn away and break that eye contact. He said that when I can learn to do that, it can help you move on to the next step. And it did help me.”

How are your karaoke talents?

“I sing a lot of karaoke songs. I’ve sung some crazy ones. George Strait is my favourite artist and I Cross My Heart is my top song. As for my singing voice, I was always the one who didn’t care about getting up there and singing first. [Former jockey] Shane Sellers is one of my best friends and he actually cut an album. He was hardcore karaoke… he had a whole sound system in his basement. He didn’t do any voice training, but he has a good voice. The thing is, he never wanted to go up first for karaoke. So, I’d go up first. I broke the ice. I’d walk in there and just step up to the mic. Shane would go up there and sound like Pavarotti compared to me, so I’d like to get my songs out of the way first.”