Remember when you were young and your wildest dreams seemed right within your reach? Back when the world was just waiting for you to make your mark, so you’d daydream all day and doodle logos on your notebooks, knowing that one day you’d be “the World’s Greatest Skateboarder.”
This is kind of like the special moment Jack O’Grady is in now, except he actually has all the talent and trajectory to make that dream a reality. At 20 years old, he’s already won the Australian SOTY award, and he’s one of Nike’s most promising up-and-comers. But you wouldn’t think that by talking to him. He’s the sort of guy you’d want to have at your BBQ: fun-loving, uncomplicated, and with a good peppering of “fucks” and “cunts” thrown into the conversation. And since he just finally moved out of his parent’s house there’s an extra air of excitement every time you talk to him.
Being such a rising star (and valuable asset to his sponsors), we didn’t think we’d get as good a laugh out of talking to Jack as we did, but the kid is nothing if not surprising. Jack’s thoughts are unvarnished and raw but not self-serious, something to celebrate from down under to the world over.
You’re from a town called The Shire, right? Do you get called a hobbit?
[laughs] Nobody says hobbit. What do you mean by hobbit?
Like a hobbit from the shire in Lord of the Rings.
No, fuck. I’ve never watched Lord of the Rings. I know what it is about but I’ve never watched a bit. Or I saw a little but I didn’t enjoy it.
You recently moved out of your parents’ house in the shire to Sydney, how has it been?
The first proper weekend I moved into the city, we had a bit of a party, we were drinking goon [laughs], which is wine in the bag like a typical 12 year old Australian, it sent me a bit south.
After, I rode my bike around with my friend Stevie. You know when you’re sort of donezo and you’re drunk and can’t pick your head up? I was in that state. I should not have been on the bike. So we’re like bombing down an alleyway, and I thought it was a big hill, but I went back the other day and it’s basically just a flat road [laughs].
There was a curb cut, I got all excited and I was like, “I’m going to jump this.” The front wheel got stuck on the full pass and I went flying.
How bad was the fall?
I went over the handlebars and went straight into bins standing against a wall. I hit my face and then just got sort of knocked out. I cut the front on my lip. And then I concussed.
That next week my lip was so fat, I had this massive cut, but it looked like a cold sore, you know? And you know when you’re walking past someone and they look at your face, you can tell they’re looking at it. I would see someone who I don’t know too well and I would be talking to them seeing their eyes looking at my lip, but they don’t know me well enough to ask me what’s up. They just think it’s a cold sore. That was the first weekend here. This city is eating me up.
When you’re skating death-defying stuff do your parents freak out?
I mean, my parents are really supportive. But every time a video comes out, my dad is always like, “Mate, that was crazy.” [laughs].
On the AM Scramble trip there’s a bit where I almost get hit by the car, and my mom and dad always freak about that stuff. They’re like, “You gotta look both ways!” Then there will be a video of me bombing hills with my friends or whatever through traffic. It’s always about things that are out of my control. Typical parenting.
“If someone comes in I just pull the sheets over me straight away”
Have they ever walked in on you while you were jerking it at home?
Yeah, a few times, but I –
A few times? That’s a lot.
It’s pretty typical, I don’t know, I would be in my room or in my bed, and if someone comes in I just pull the sheets over me straight away. I don’t know, I haven’t been caught-caught. But I’ve never had a lock on my door. Also, my house is wooden, you know? So if you’re up to something in your room you’re listening to everything. But if someone is walking in the hallway I could hear them coming.
What, do you live in a shack?
What are you talking about! A shack?
A wooden shack, is that what you’re talking about?
What, you’ve never been in a house with wooden floors?
[laughs] I just imagine a beach shack in Australia.
Ahh fuck. Typical American. Like, did you ride your fucking kangaroo to school?! [laughs]
So when they walk in on you jerking off, are you going imagination style or do you have a computer or something next to you?
I never really liked getting stuff up on my laptop because that’s just sketchy. It’s a big screen. So I just use the phone. But I’m not just going to throw my phone if someone walks in [laughs].
I know you used to clean pools, are you skating full time now or still doing that work on the side?
Nah, I haven’t been a pool boy for about a year now. It’s a blessing every day to not have to work. Like obviously, I was cleaning pools and that’s a chill job, but working a 9 to 5. I sometimes forget how lucky I am not to have to work. Skating is a job, but it’s sort of not at the same time. You just get to go on holiday all the time [laughs].
What other jobs have you had in your life so far?
When I was 14 I worked at this skate shop that I ride for called LoDown and I worked at a pool shop too. When I was 17 I used to work for a chemist as the delivery boy. I used to deliver all the medicine to all the elderly people who were subscribed to the chemist that couldn’t drive. I did that on my bike. But then, I got my license.
But at this job, there was this big mean guy named Sam. I was always really scared of him because he was really intimidating and he never smiled or spoke to me, he just always yelled at me.
I think it was the last couple of nights I was working there. It was me and him in the shop and he started asking me if I was seeing any girls or whatever. I was like, what the hell? [laughs] And then he fully opened up to me and he started telling me all these stories about the chicks he used to get back in the day and he’s like 45. But it was such a weird turn from just not talking to me and being a weirdo and then just like trying to bro down with me and talking about chicks.
Do you think it’s important to have jobs like that?
Yeah, I think it’s really important because it taught me about life and I need to earn my keep. It also taught me that I need to work for something. Skaters come into the scene and are picked up by sponsors and they’re getting checks straight away. They don’t really have to do fuck all if they’re getting a fat check from these big brands. They don’t really know. Then it’s like at the end of their career when they’re 30 – some people will be like, “This is so hard,” but you’ve never worked a proper job and you’ve never seen the other side. You’re just chilling right now, but you think you’re doing shit because you’ve never had a real job. So I think it’s really important.
But skating as a job can be stressful as hell too, no?
I guess it depends on the type of skater you are and the types of sponsors you have to deal with. For some it can be. I feel like the only cunts who are under pressure are the big dogs in the scene that have to be working on shit all the time and have to be coming up with shit. Doing interviews like 24/7. Like fair enough.
Why do Australian’s love saying cunt all the time?
In Australia, it’s just so normal and you don’t even think of it as a swear word. It’s in your everyday vocab, you just say it so much.
Do you feel like your friends or acquaintances treat you differently now based on the success you’ve had so far in skating?
Not my friends, but I noticed people saying what’s up to me and people trying to hang as I get older.
There’s this one guy, back in the day he used to be in the scene or whatever, if I saw him around he wouldn’t say what’s up and he’d cool guy me a lot and just be like who is this little kid? But now, I start riding for Pass~Port and he’s like “Hey! How you doing!?” I’ll talk to you but I’ll never forget when you cool guy’d me when I was fucking nothing. When I was just being a kid and giving you eye contact to say hello and then you turn away.
Do you think I forgot that? That’s just one example but there is people like that everywhere.
If someone has cool guy’d you, even twice, you’ll never forget – at least for me. Like, oh now you want to talk to me? What about when I was trying to say hello as a little kid who didn’t know anyone? If you didn’t want to talk to me then, why are you trying to talk to me now?
Did you do anything unusual during some of this quarantine downtime?
When I was first in quarantine I started this painting of my two friends [above] who passed away this year and last year. So I’ve been working on that. Lately, I’ve been waking up, having some coffee and if it’s sunny I’ll go out for a bit, and then painting on this big canvas.
That’s a skill you’re just picking up?
No, I used to do art in school. But when I was 12-18 I was really into graffiti. Now if I’m out and someone has a tin or marker I’ll do a tag, but nothing too crazy. But this piece is like an actual painting. I haven’t done a painting like this in a while. But it’s good, I like it. It’s almost, sort of, there.
Is it true you were dating the sister of Dustin Dollin’s wife?
Yes, it is true we meet when she came to Sydney at the start of the year it was a bit more than some summer love it was really nice.
She just DM’d you randomly? How did she know about you?
[laughs] Yeah she did, and I have no idea how.
So it was just you, Dustin Dollin, the two sisters and the rest of the family?
You can’t make this shit up. This is like a family portrait!
[laughs] Ever since I’ve dyed my hair black – people are like, “Oh, you’re trying to be like Dustin!” It’s like no! I just dyed my hair black and I sent a photo to my friend George and he was like, “Oh my god, you look like Dustin!” I was like “fuck!” [laughs]
But why don’t you like that?
It doesn’t matter who it is, I’m not trying to be anyone else, I’m just trying to be myself. I want to try to be my own person and be known for me not someone else.
Is there anything you’d like to learn or get better at in life?
I feel like I’m okay at talking to people sometimes, but I would like to get even better at going up to someone and having the confidence to say what’s up. Something I would like to get better at is just being smarter in general. Sometimes I feel like a dumb cunt, like I want to know some everyday stuff.
I learn so much just hanging out, in the city and being around, than I did at school. At school, you know you have all your subjects and shit – you should have a life subject. Like when something happens in your life and how to deal with it.
“I don’t want to ask my dad which is the right way to shave my pubes”
What would you like to put in “Life” the class?
Maybe how to talk to a person properly, like proper manners. I guess you get told that in your house but some kids don’t get that. Also, learning about yourself and teaching you that you can listen to yourself and find your own self. I don’t know.
Teach people about being hungover or some shit. Like random things, shaving with a razor – I don’t have much facial hair but I didn’t know which way to shave growing up if I had to pull up or stop then go under my chin. Or if I do it the wrong way will it hurt my skin? My dad never taught me that, that’s fine, my dad has taught me everything else. But that’s a small little random thing that could be taught in class for like 5 minutes.
When I was younger I used to shave my pubes, but now I let it run, like I don’t really care. But maybe they could show you how to shave your pubes. Something you might be embarrassed to ask your mum or dad about. I don’t want to ask my dad which is the right way to shave my pubes.
Those little sex-ed things are the things nobody tells you. Kids are scared to talk about that and don’t know how to ask about that. It’s the things you keep to yourself. Someone young should be teaching that class too. If I’m running that class and I’m 40 then I’ll stop teaching the class.
What was your dream as a kid growing up?
My whole dream growing up was making it in skating and moving to America for a couple of years and living the regular skater dream, Still is. That’s all I really want to do. It’s a big thing, cause it’s sort of like when you move to America you’re like, “Ah, I’ve made it.”
I look at Lucas Puig, who is a huge name, but he’s never lived in America. Have you ever thought of staying and making it in Australia?
Yes and no. There’s not enough money in skateboarding in Australia to just skate. You have to work a job and then also be fucking paid to skate.
So you’re saying if you never leave Australia as a skater you can’t make a good living?
No, you can’t, and it doesn’t matter what company you ride for. It’s just how it works and it’s the way Australian skaters are brought up, like, “Alright if you want to make a living off skating you sort of have to move to America.” Everyone in Australia knows that. And some of these people are working 5 days a week and then still fucking killing it.
If you want to make a proper living you have to move to America for a bit. I feel like that might change in a couple of years, but for the last 10 years that is how you have to do it to get recognized out there. But I know in the Euro scene they could get hooked up and still live there.
But you’re getting by right now in Australia skating full time….
Yeah I’m getting by, but I’m 20.
Chima moved to The States too right?
Yeah, Chima [Ferguson], moved I think when he was 21. He moved in with Dustin [Dollin] for a bit. He lives back in Australia now.
The European scene has had a boost of energy over the last couple of years, I think Australia could be next. What you think?
Oh, for sure. There are so many fucking skaters coming out of here. Rome Collyer. Rowan Davis. I know you guys had that part, he’s fucking insane. Sam Sutton. He can tre flip up some shit and over some shit and that’s a rare talent and this cunt has them. There are so many young kids and even like the young kids at the skate park who are just fucking around I see them and I’m like fuck they’re going to be next.
If you could have anyone’s pro skateboard career, whose career would you emulate?
I don’t know. I sort of like look at people like John Cardiel, that name lives on forever. He’s just a legend, and everything happened with him, but everyone is still fucking talking about him. He’s still so present in every day and every generation of skateboarding. That to me is the coolest thing ever.
You’ve been named Australian Skater of the Year, had covers and a lot of success so far and you’re really just starting. How do you not let it get to your head?
I mean, there are certain things where you’re like, “I can’t believe that all this is happening.” It might feel a bit crazy if I’m in another country on a trip trying a trick, but if I’m in Sydney or whatever just hanging out with the cunts I feel the same that I felt before. I’ll wake up just like normal. I’m over the moon how things have gone so far, but you can’t think about that. People let that shit get to their head and you forget you’re just a normal person. I’m Jack from Sydney, you know what I mean?
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