October 21, 2020/ / ARTICLES/ Comments: 42

I’ve been trying backside tailslides for about 30 years now. They’re my white whale. In fact, the attempts I filmed of myself on a step in front of my school bathroom 25 years ago are frighteningly similar to what I can manage today.

To me, the backside tailslide is one of a select top shelf of tricks that are simply better than all others, sitting alongside its flashy cousin the backside smith, 360 ollies, and, I don’t know, switch crooked grinds.

A good backside tailslide looks completely natural as if it’s not an almost incomprehensible combination of movements performed within a period of two seconds. There’s something about getting your body all tucked-up and drifting sideways that encapsulates why skateboarding is the coolest shit ever and why I have been completely bewitched by it since I was 12 years old.

Over the years, my favorite skaters have always been back tail guys: Jason Lee, Mike Carroll, Salman Agah – the older brothers I never had. I suppose the urge to be cool, to be the type of person who can backside tailslide, has never left – and that urge is the root of a lot of the anxiety and dissatisfaction in my life. As my mum once said: “You want to be John, but you’re actually Paul.”

At the age of 43, you’d think I could give up and settle for my average bag of frontside-leaning tricks, secure in the knowledge that at least I gave it a shot. But that’s the problem: I still want to be a back tail guy. I still want to be cool, however pathetic that sounds.

me front boardsliding in 2000 / photo: gillespie

30 years of failure

There have been a few battles over the past few decades, beginning with the initial teenage phase in which I sort of learned back tails the way that I sort of fumbled my way through every trick. Looking back on old footage of myself skating is akin to watching footage of me drunk at a party. It’s much messier, slower, and less entertaining than I remember, but I still feel a sense of pride in my unknowing charm.

Then there was a brief window of time when I was actually a contender. I had a firm grasp of most basic tricks and I was unafraid. I can remember ollieing into backside tailslides back then and feeling them within my reach; there was even a day that I actually landed a couple to fakie on a knee-high ledge in a closed-down used car lot. Then I tore my ACL in 2000 and had to sit out a year, and was never able to claw that confidence back.

The last time I really tried to learn them was probably about ten years ago. I’d been trying them for a month or so pretty solidly and was coming close, but slipped out on an attempt and bashed the entire front of my body on the ground. I fractured my thumb and bruised my chin, both shoulders, my testicles and hips, knees, and one ankle. I guess that put me off for about a decade.

The Plan

Around the time the COVID-19 pandemic struck in March and everything suddenly stopped, it occurred to me that I should dedicate myself to learning backside tailslides before normal life returned.

At that point we had no idea when that would be; we still don’t, I suppose. I knew that I’d be skating by myself for the foreseeable future, anyway, so I could practice the trick for hours without embarrassing myself. It also gave me something manageable to fixate on beyond the terrifying sci-fi novel playing out in New York.

Like everyone else, my wife Rosie and I were cooped up in our apartment, trying to keep the mood light for our five-year-old son Fred while we obsessively checked the news for updates on whether we were all about to die.

To make matters worse, we were still very new to NYC and hadn’t had time to establish a strong network of friends that could take the place of the family we’d left behind in New Zealand only a few months beforehand. The potential for adventure and discovery of being in a new city was replaced with a dull feeling of alienation and loneliness that couldn’t be shaken by simply striking up a conversation with someone on the street.

Through all this, I distracted myself with the fantasy of the backside tailslide. I imagined the sensation of doing them as I lay in bed. I tirelessly researched them online.

I followed the @bstails account and studied every post for clues; I watched all the YouTube tutorials and wrote down motivational tips on my phone (crouch, approach with open shoulders, pop, then watch tail). I revisited my favorites, I observed the new generation. I slipped out of the house every other night after dinner and tried them for an hour or two at the curb a few blocks away. I returned home no closer to success.

There was no real reason why I couldn’t do it. I’d definitely put up some mental barriers, and deep down I believed I simply wasn’t good enough. A big portion of my solo sessions consisted of warming up to the point where I could summon the courage to even hop onto the curb in the back tail position. And once I got into a few, I feverishly tried them for as long as possible before I felt my vision blurring. I was swinging in the dark.

There were a few close calls.

About a month ago, I spent an intense half-hour or so tricking myself into thinking I was comfortable until I got into one that slid a little. After a few more, I slipped out and grazed my elbow. Within ten more tries, I rolled away. The footage tells a far less heroic tale. It’s hardly a tailslide, more a quick skid – and the way I did it was still pretty weird. But it was, undeniably, sort of a backside tailslide.

A trick begins from the moment you push off, really; your approach dictates the outcome. That’s why skating with your best friends always brings out the best in your skating: your confidence grows and you feed off each other’s energy. There’s always a split-second before you pop though, where you’re on your own. You have to fool yourself into believing that this will be all right and that you can do it. If you know you’ll land the trick, you probably will. And if you allow a distracted or fearful thought into that moment, then you’re fucked.


Occasionally during the long, tense days of homeschooling my son, I felt as if I had experienced a breakthrough. I could almost feel myself learning the trick mentally. Later that evening I tried out my latest theory at the curb, only to be confronted by my own ineptitude. I’d persist for an hour or so and sometimes kid myself that I was getting closer, but it never actually gelled. Even though I knew what I should be doing, I still couldn’t do it.

I suspected I may have waited too long. After 30 years of skating, my skills were baked-in and atrophied, my fear of falling too high. The distant memory of failure and injury lurked beneath every attempt, holding me back from committing in the right way. Perhaps this was the end of the road?

At some point when it started getting warmer, I gave up.

Backside tailslides were simply too frustrating for me and I was sick of struggling. I preferred to do tricks that came more naturally; I tricked myself into thinking that was a more intuitive way to skate. But still, it wore at me. Every unemployed barista at the skatepark could do a back tail; why couldn’t I? I knew I was overthinking it, but thinking was all I had.

Trying (and failing) to learn backside tailslides reminded me yet again of how incredibly difficult skateboarding is, as well as an invaluable escape from the rest of life.

I may not have learned my dream trick; but in the meantime, I had become a better skater. I learned other tricks, got better at the tricks I could already do, and was less scared to try things outside of my comfort zone. Skateboarding was rewarding me for my diligence, but just not in the way I wanted it to.

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  1. Steve

    October 21, 2020 5:59 pm

    As a 35 year old who once had this trick (17 years ago), I am now inspired to get it again

  2. Drew

    October 21, 2020 6:17 pm

    They’re easier on transition

  3. Circle to circle

    October 21, 2020 7:37 pm

    I always found this trick to be easier the faster you go; don’t approach going 2 MPH at the ledge, because you will slip out and end up on you chest. Having a proper BS 180 is the starting point, and come at a slight angle, not parallel. And most importantly, commit to putting the tail on the ledge and sitting on it. Also, if you do learn it, it will feel awesome, but I think doing them on transition is even more exhilarating, especially on concrete if you get the barking wheels, too. Best luck, and keep trying.

  4. Ron

    October 22, 2020 12:07 am

    BS Crail slide….now your talkin !!

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