I probably didn’t need to, but I’m starting this sequence from the tail stop, if only to illustrate one key point…

…and that’s that the transfer into a 50-50 position will lend a certain degree of flow into the move. You don’t need to balance for long, and stopping to pogo will actually make this look considerably worse.

Case in point: as soon as I get into the 50-50 position, I’m already leaning down with my back hand, ready to grab something underneath my foot.

As I get closer to my back foot, I’m extending my front foot behind me slightly to help counter-balance my posture…

…and I finally get a solid anchor point with my back hand while the nose drops down, continuing the swing up that started from the tail stop. One fluid motion is the goal here.

You can theoretically grab anything under the back foot – either wheel or the truck itself – but from this angle you get a better view of my ass the fact I’ve got a solid grip on the heelside wheel. Grabbing the truck may be tempting, but generally, grabbing the wheel is the better option.

Going back to a front-on view, you can see that the nose has continued to drop and now it’s only really my fingertips holding it up. Meanwhile, my front foot is coming in, ready to land on the underside of the nose.

This is the most important frame in the whole sequence. I’ve simultaneously hopped upwards, let go of the nose, and pulled the tail off the ground with the back hand. You don’t want to just drop it – you need to go airborne to make the sidewinder work.

…and this might be the most controversial frame. The original way to do the sidewinder was to put the front foot on the underside of the nose before you let go, but I find this jump-into-position approach flows better, personally.

Now my front foot is in position above nose, and I’m still pulling the tail up using that back wheel. This is crucial: the worst thing you can do with a sidewinder is let both the nose and tail touch the ground at the same time.

At this point, the sidewinder is technically complete – my front foot is solidly under the nose, the tail has been kept off the ground, and my back leg is extended behind me for balance. Textbook – but we need to get out of this position so we can roll away.

There’s many options here, and the way to get out will depend a bit on what you grabbed with the back hand. Having grabbed the heelside wheel, I can take the easy route and just do a half flip, so I start with a little hop, pulling the board up in the process…

…while also flicking forwards with my back hand to get the board back to a regular riding position. I’m quite tightly balled up here – careful not to knee yourself in the chin as you swing your back leg in for the landing.

The back leg is going to have to connect first to “catch” the board in mid-air and level it out. Of course, make sure you’ve let go of the wheel at this point or you’ll rip your fingers off. This is one of many reasons grabbing the wheel is better than grabbing the truck, incidentally – easier to let go!

Finally, the back leg has pushed the board down to the ground, the front foot has found the griptape again, and I’ve landed solidly, ready for the next trick.

Additional Notes

In theory, you can do Sidewinders on basically any board, but they become significantly easier on a squarer tail, as it’ll help stabilise you when you’re standing on the truck. If you’re using a popsicle-shaped street board, consider flattening off the end of the curve; I used to use an orbital sander when I was 14 or 15 years old, but I’m sure you can find something better than that!

This is still possible on longer boards (like street boards), but it’ll be far harder to hold the nose up while reaching down to the back truck – and a longer stretch to get the front foot on the underside of the nose. Also, steep noses (like you get on street boards) are harder to land on, and your front foot is more likely to slide off. Basically, what I’m saying is… don’t use a street board if you can help it. A dedicated freestyle board is going to make your life a lot easier!

Even if you don’t want to use a freestyle board – maybe you can’t afford one, or maybe you just hate yourself – it’s still worth picking up some skid plates before you start working on these. Razortail and truck tricks don’t mix; standing on the end of a razortailed deck is an easy way to totally ruin your board.

Finally, I mentioned it in passing, but resist the urge to grab the truck as you pull the board up. Not only do you risk getting tangled and not being able to get your hand out quick enough, but there’s a good chance that you could rip your knuckles up on the mounting hardware in the process. The knuckles on my right hand still bear the scars from doing exactly that back in 2002, so learn from my mistake and grab the wheel instead!