We’ll be the first to admit that “Selling Out” is kind of a dying concept. These days, getting sponsored by a kooky energy drink or headphone company isn’t the nail in the coffin for your “core” skate career, and many of our current day favorites like Ishod Wair or Louie Lopez are hooked up by these very brands.
But as we know, things haven’t always been that way. Back in the day, many skaters just took the big corporate check and smiled to the cameras as the sponsors ran wild with terrible ads and corporate logos plastered all over their deck and face. And while these ads had the potential to damage the skater’s credibility for life, it gives us an opportunity to look back and laugh as these dudes presumably roll in their piles of dough like Scrooge McDuck.
To celebrate some of skateboarding’s more memorable money grabs, we got lost in the Youtube wormhole for the most awkward commercials where skaters-at-large collectively kind of just went, “What the fuck?” I hope the check was worth it!
Nyjah Huston for Lance Bolds
Dudes have some weird, uhh… “sponsors” now that skateboarding is “influencer marketing” for 3rd rate startups, but at least riding for a coconut water company makes some sort of sense. Coconut water is sick as fuck, and you get dehydrated when you’re skating, so it’s a useful product. But have you ever tried eating a fistful of salty orange crackers without a glass of water or something nearby? Shit’s impossible, even when you’re not all sweaty and dry-mouthed from skating in the summer heat. Do you, Nyjah, do you, all I’m saying is it’s not an ideal snack for the skater on the go!
Bam Margera for Rite Guard
One thing that I’ve realized recently is that skateboarding kind of outgrew the label “Extreme” places upon it by mainstream morons. During the ’90s and ’00s everything associated with skating was XXXtreme (even this shitty deodorant is called Rite Guard Xtreme), but recently we’ve become more of an “Action sport,” and because of the Olympics… now we’re just referred to as plain ol’ Sport. Anyway, this may be the most unashamedly blatant ad on the list, but at that time Bam was already a huge mainstream star and was apparently paid 1 million to do it.
Tony Hawk Bagel Bites
By 2002 Tony Hawk was pretty much a household name, at least in households with video game consoles. He’d already boned a frontside air with a milk mustache, 900’d at the X-Games, and was Boom-Booming and Huck-Jamming across the country. That’s what makes this Bagel Bites commercial so great – this wasn’t Brian Sumner shilling for the Diet Rite of mall-punk hair dye, this was THE pro skater at arguably his commercial peak, selling stoner snacks to tweens. And whoever directed the ad clearly had no idea what to do with a skateboarder. “Uh… just stand there? On your skateboard? Yeah, and take the kids food from them. Sick…?”
Colin McKay’s “Double-Fakie-Ollie-Grind” for 1-800-COLLECT
This one is full of anachronisms from a bygone era, all sorts of relics that most readers won’t remember: the phone company MCI (now Verizon), pay phones, Colin McKay, vert skating, Alyssa Milano dressed hella late-90s… Back then you didn’t need a safe spot to stash your phone while you skated — the phone’s over there on a pole and it costs a quarter, dummy! Nobody can blame Colin for not making the “double-fakie ollie grind,” because what in the actual hell is that? I don’t have my encyclopedia handy, but I’m pretty sure this is among the first times an apparently clueless piece of mainstream media created a skate joke that stuck with skaters.
Double Pits to Chesty by AXE Body Spray
This one is a real treat because we get a trifecta of skateboard cash cows at the time: J Casanova back when he was still Jereme, peak teen heartthrob Ryan Sheckler, and the non-skate-sponsor king himself Greg Lutzka. The Trio of Energy Drink Pros star in a “short film” based on landing the elusive “double pits to chesty.” This one along with Life Of Ryan single-handedly tainted Ryan’s career for life, which is why he chose to just shut up and skate ever since.
Ray Flores for Pepsi
This is a case of selling out before selling out was even a thing. In 1978, Pepsi got behind one of the best pool skaters of the time and put Flores on their payroll. Although skateboarding back then was rebellious and edgy, the commercials tell a different side of skateboarding. Though Pepsi may have gotten the attitude of skateboarding all wrong, they still brought skateboarding to people’s living rooms and normalized it to an extent. Not to mention that barefoot 360 might be the most outrageously fake but gnarly thing supposedly performed on a skateboard ever.
Rob Dyrdek kickflipping a Chevy Sonic
This has got to be one of the most absurd and insane ways for a skateboarder to get some extra advertisement money, so, of course, it would include master marketer Rob Dyrdek. He wasn’t asked to skate, or even fake doing a trick in a car like Tony Hawk for Jeep, Dyrdek actually kickflipped a Chevy – the whole fuckin’ car. Granted the ramps were set up so he basically just had to drive straight and fast and close his eyes, but I’m sure his eyes were open wide when he took that check to the bank.
Jason Dill on The Osbournes
Not sure if this one is really a fair “sellout moment” because Jason wasn’t really in an advertisement or taking a sponsorship deal here, but we’ve been told that he did get paid for his appearance on the The Osbournes aka the biggest show MTV ever had. Rumor has it, he was friends with (and freeloading off of) Ozzy’s kids for a while, so once the show came around, it was only natural he stop by and be a part of an episode. Sure it’s a little cringy, but who wouldn’t want to hang out with The Ozzy Osbourne, his millionaire spawn, and get paid to do it? Who knows, maybe we have MTV to thank for secretly funding FA.
Alex Olson for Sweet Spot
Alex Olson has flirted with various modeling / commercial gigs for a while, but this “Sweet Spot” ad takes the cake. So what is it exactly? Well let’s just say you’re having an amazing romantic picnic and you’re a bit nervous about your smell, you know… down there. Well, Sweet Spot, has you covered! Just make sure to run to the bathroom and wipe down your stuff before settling down and pretending your vagina always tastes like lavender soap.