11 years ago a relative comedic unknown suited up in front of a camera and commenced to talk shit on everything and anything in skateboarding and Skateline was born. Garnering friends, fans, and haters, through the weekly show and a coveted partnership with Thrasher Magazine, Gary Rogers has become skateboarding’s defining voice in satire and most importantly, reminding everyone to lighten up. 

Like any online or on-air personality, there are levels to it, and Gary’s more than just a quick wit with a surplus of snaps. Through his platform and popularity, he’s done more than roast your favorite skater. In fact, his approach is “hate for good,” breaking off a piece for his friends and the skate community through several businesses and initiatives focused on getting everyone a seat at the table. 

With Everyday Skate Shop, Black Gold Grip, Permanent Holiday, and his breast cancer awareness nonprofit Pushing For Pink, Gary’s dead serious about skateboarding and its community, so we chopped it up with him for Common Threads to learn more about the real personality behind all snaps and laughs.

Photographs by Justin Ching

Everyday Skate Shop crew seen wearing HUF Summer 23

What got you interested in comedy?

My dad's a huge comedy fan: Eddie (Murphy), Martin (Lawrence), Dave (Chappelle), and Richard Pryor, but he didn't let me get into Richard just because of the language, but he did let me get into Martin because it was like family comedy—‘90s shows… the Wayans Bros. One of my first movies is Friday. All the old legends, they were my family. And then just not wearing lotion to school was how I learned about roasting and making fun of people. But what made me actually want to do things like Skateline is in 2005 in front of FTC, I ran in Dave Chappelle when he came back from Africa. He was shopping and he was doing those multiple-hour shows at nightclubs and that really got me because I made him laugh, just messing around talking and shit. So that put that battery in my back for real.

 So how does that fuel Skateline. You mentioned that initially, you wanted to do a skate version of The Soup.

There were some similar shows coming out at the time, but the homie Joel Jutagir from Metro Skateboarding was like, "We should do our own. You never copy," and I was like, ‘Oh, well, these shows are successful.’ He's like, "No, you got to do your own thing. I feel like you in a suit, at a desk, making it more like The Daily Show mixed with Soup. This would be different for skateboarding.” 

Captain and Casey kind of had it back then, but there were certain jokes they couldn't say, certain energy they couldn't have that I was able to have in skateboarding. He was like, "This will be brand new." And I was like, ‘Holy shit.’ So he's just a genius. So that's why it just all fell into the right hand. I knew exactly what he meant. So when I sat down, he was like, “Go!”

I used to freestyle all the skits at first.

Does it get harder as you go along when you know more people and shit like that?

The only thing that has gotten harder is the sensitivity of the world and taking jokes seriously and then I'm still like, ‘Fuck it.’ It's hard on me. I think I need to grow up, but I can't. Skateboarding knows we're joking at this point. It's been going on for so long. It's housed by one of the biggest names, if not the biggest name in skateboarding. So people are like, "He has to just be messing around." Jake (Phelps) used to kick your board while you're trying to trick down a fricking 19. So it's at least I'm not in your face. Well, sometimes when I go to a contest… [laughs]

A lot of older comedians complain about sensitivity—that they can’t do their old bits. How do you evolve over that 11 years of doing this and thinking about how society changes?

There are smarter ways to tell the joke, and having somebody like Joel, we are able to guide these things. And then also having the relationships and the friends with people that are in the LGBTQI+ community or people of different races and backgrounds, they are like, "This is what you should say and how you should say it," not telling me what to do because I'm going to do what anyway. I think everyone gets it because you have to have those relationships, but yeah, certain people don't. When the person knows you, they're like, "Oh, that's Gary.”

So I didn't have to evolve because I'm willing to learn and understand people in all facets. I'll try a joke just with somebody that's of a different life and I'm just like, “How did that go over?’ Sometimes it works, sometimes it doesn't. You have to evolve with kindness. You can't be rude and shit. People actually have ... they got malice in their speech and I just don't. I'm just an idiot that has ADHD, just rambling and motherfuckers be like, "Ha-ha."

Being from the Bay Area and having the backing of Thrasher has to be a big deal to you…

Having that Thrasher support is bigger than ... I don't put my name in stone because I never had the footage and I didn't super skateboard and that's what I really love, but I get to sit at the table with the guys and I think that that's cool. I appreciate that. I never had my name on a board or nothing like that, but I'm excited that I get to be a part of Thrasher. That shit’s hard. It's like 40 years of legacy and then I'm raised literally… you make an L from my grandmother’s house and you could get to where the warehouse is. I was raised literally a three-minute drive, a two-minute drive from Thrasher. There was this super old park that had a bowl near there too. It was just cement… a rail and I think a three-stair that you couldn't skate. My grandmother actually took me to that because her name was Ollie. Yeah, so my grandmother's name was Ollie. I was raised around the corner from Thrasher, and then when I moved back to the Bay Area from Sacramento, the skatepark across the street from my house was Thrasher Park.

I want to get into something that came up earlier. I really like that your whole approach to comedy… to everything is almost “hate for good.” You know what I mean?

I come from a really poisonous life, so all the attention… I did it so I could give back. I don't have a sense of greed. I don't want anything for myself. I got everything for myself. So that's why I hate for good, as you said. That's why I want a shop. That's why I do the giveaways, why Pushing For Pink literally takes all the highest marketed stuff from the skate industry and knocks it off 60-70% off. I just do that. For a day, I just want to spoil everyone with what I’ve gained from doing this. Sometimes I’m like, ‘I wish I was higher up. I wish I had everything. I wish I cared to play the game a little bit more to get higher up, so I can give more." But now I'm just like, ‘OK, let's start a business. Let's start the grip tape company. Let's start getting collabs off. Let's get the cannabis company straight.’ I don't even smoke weed anymore, but the bros started one and they were like, "Yo, we need a creative director, all these things." I was like, ‘Let me hop in. Let's do this. When we open this dispensary, let's go crazy,’ because there are all these companies that want to market skateboarders and the weed and stuff and they don't know shit. 

And skate shops… they can be some cool guyed, bullshit. Having to do the shoe game. I don't want shoes in my shop. Go get shoes elsewhere. Support them. You come to me. You grab a board. You get treated nice. I got guys in there now that are not finna cool guy you. I got all good energy for when you come grab a board and then you can come to the safest and richest neighborhood in San Francisco to get that board. Everything is directed toward mental peace, but I'm just talking shit. Every other day of the week, I'm roasting you. I'm humiliating you. I'm just, "Ah, fuck you. Your shit weak."

Do kids run up on you and want to get roasted?

For a while, it was the phone in your face, "Say something funny," and I'll just look at people like, "Bro, no, that's not what's going on?" I'm not trying to be fucking Suge Knight." Kids still will run up and try to have fun, but then quickly start to pick up on the energy of, ‘I'm willing to be funny and have a good time, but I'm not sitting here as a personal joke, but I do want to help you in any way I can. I do want to help you if you do want the video or do want the pick, but just don't get it twisted.’

Can you talk about having Everyday in Union Square and why you chose that location?

So my boy, Johnny Roughneck, he's already had a shop called Everyday and it was in the Tenderloin. So he had the shop and he was like, "Gary, I got a space in Union Square, right in Union Square.” I’m like, ‘You just had one near the crack house. Now even have it near the nicer crack house?’ But he said, “Nah,  it's going to be small, but it's going to be fire. Partner with me, let's do it. I got this other partner who's going to put the money down and I'm going to trust you." And I was like, ‘Damn, you're going to trust me with a skate shop. Fuck yeah." So I did it.

So you got the show, the shop, Pushing For Pink, grip tape, cannabis… what are we missing? [laughs]

Pushing For Pink, Black Gold Grip. I get the samples for my clothing. I was going to do just grip tape, but I was like, ‘All right, let me try to do the clothing thing. See how that goes.’ Pushing For Pink, we got an event coming up later this year that's supposed to be sick. We're going to stay away from the festival thing for a little bit because we threw the best festival we could and now we're like, ‘We need to raise more money to actually throw a Coachella-style festival.’

And then Permanent Holiday, our dispensary should be opening in the next couple of months in the city. And Everyday Skate Shop. Go by there, get your board, get treated nice. You don't get judged. Don't get cool guyed by a dude that has a room in a house somewhere and fucking thinks he runs the world. Fucking untuck the wedgie out your ass, bro. There's no point. They're children. Children like this thing, so stop fucking looking at them like that, stop talking to them like that. It's not their fault that you're unhappy.

In the 11 years that you've been doing Skateline and really on the ground and skating, what are the biggest changes you've seen as an observer that you feel are some positive changes? 

A lot more of my friends made it. Tyshawn's been SOTY and the inclusion. That’s a catch-22 though. I wish everybody looked at skateboarding and how skateboarding was from, let's say, '97 to 2008. You have to go hard. I really like that everybody can do it. I like how the respect has changed for it. I think that the Olympics was a joke though… fucked things up. I still want to host one though, just so I can ruin that.