At least he had some fun with it. Jason Dill and Ryan Sheckler, 2008.

A lot of work goes into pairing up skaters with the right team. This being the case, it's always interesting to see obvious incongruities between a skater and a brand they represent when they happen. Sometimes the fit seems right at the beginning and a skater changes the way they skate or dress over time. Sometimes, a brand tries to make a power move and doesn't clearly see what's going to happen if a certain skater is associated with their product. And sometimes, skaters seem to be put on teams without much consideration for how they'll fit all.
Here are a few of our favorite skater / sponsor mismatches:

Jason Dill on Etnies
It's weird when you get a skater who's known as a 'cool guy' endorsing a company that's struggled to identify with 'cool' skateboarding for most of its existence, but it happened. According to Dill's interview on The Chromeball Incident, "riding for Etnies was the worst move I ever made in my 'career'."

Greg Lutzka on Krooked
We've brought this up with quite a few people, and no one we talked to (except James from Labor) remembers Greg Lutzka on Krooked. Although it seems like an odd stylistic pairing now, this actually made some sense at the time. Lutzka was an up-and-coming skater with some heavy moves and Krooked was a new company stacking its roster. Here's the ad as proof.

Bobby Puleo on enjoi
It's hard to imagine Puleo's brand of East Coast weirdness coexisting with enjoi's West Coast goofballery, but they did for a short time. According to a Transworld interview from last December, the relationship didn't work out due to Puleo not wanting to film a video part in San Jose. Can't blame a dude on that one.

Gino Iannucci on Black Label
For those of us under 35, this was shocking to find out whenever it came up in a conversation with an older skater. Black Label = hesh, Gino = fresh. But at one point Gino was a kid who needed some boards and John Lucero was down to send him some. It's explained in Gino's Epicly Later'd how it all worked out.

Andrew Reynolds on Fourstar
Is it just us, or was it always kind of weird to see Andrew Reynolds in Fourstar ads?

Anthony Van Engelen on DC
This one made sense for a lot of reasons – the Workshop & DC connection of the late 90's, AVE having a mean bag of switch tricks, and the wearing of baggy cargos cinched well above the ankle should all be considered. That being said, it's still weird to look back and see a guy who we think of these days as synonymous with Vans, flannel shirts and 70's rock in a pair of puffy tongues.

Bob Burnquist on Antihero
Pre-X Games stardom and well before his Base jumping career took off, Bob was a shredder of concrete bowls and fit nicely on the Anti Hero squad. In a 2013 Transworld interview he broke down why he and the screaming eagle parted ways:

"I outgrew it. They had a different mentality. Skating in the X Games or any events like that was completely the opposite of the proposal of what skating for Antihero was. But to me it was all the same. I just viewed it differently. To me it was just like, 'I’m gonna skate it all. I’m gonna skate everything I can. And I’m going to make a living off of skateboarding.'"

Josh Kalis on Toy Machine
We could have gone with a few different skaters on this one - Toy bred a lot of skaters who eventually established looks & styles that differed greatly from what became the brand's vibe. Chad Muska and Jahmal Williams also got their starts on Toy Machine, but we settled on Josh because of this quote from his interview with The Chrome Ball Incident regarding his relationship with Ed Templeton:

"I didn’t really go up to his house all that often. But when we did go, it honestly kinda sucked. Like, if I was cold at a spot, he wouldn’t let me wear one of his extra hoodies because of my smoking. Or I could never eat my Carl’s Jr. in his house because he didn’t want his place to smell like meat."

Thanks to The Chromeball Incident, Skately and Transworld.

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