I’ve been chasing the backside tailslide for about three decades now. It’s my skateboarding enigma, the trick that has eluded me despite countless attempts. The frustrating truth is that my tries today are eerily similar to those I filmed 25 years ago in front of my school bathroom.
To me, the backside tailslide is a top-tier trick, ranking alongside the likes of the backside smith, 360 ollies, and switch crooked grinds. It possesses an allure that’s hard to describe.
A backside tailslide in action, showcasing the tucked-up body position and sideways drift
A well-executed backside tailslide looks effortless, almost natural, despite being a complex combination of movements performed in mere seconds. The act of tucking your body and drifting sideways perfectly encapsulates the magic of skateboarding and why I’ve been captivated by it since the age of 12.
Over the years, my favorite skaters have always been those who mastered the back tail: Jason Lee, Mike Carroll, and Salman Agah – the cool older brothers I never had. The desire to be like them, to effortlessly perform a backside tailslide, has been a constant driver in my life, though it has also been the root of anxiety and frustration. As my mother once wisely observed: “You want to be John, but you’re actually Paul.”
Now, at 43, one would think I might give up and be content with my average bag of frontside tricks. But that’s the problem: I still crave the feeling of being a back tail guy. I still yearn to be cool, despite how absurd that may sound.
Three Decades of Setbacks
My battle with the backside tailslide spans several stages, starting in my teenage years when I “sort of” learned the trick, much like I fumbled my way through most tricks. Watching old footage of myself skate is similar to watching myself drunk at a party: messier, slower, and less entertaining than I remember, but with a naive charm.
There was a brief period when I was actually making progress. I had a solid grasp of basic tricks and was fearless. I remember ollieing into backside tailslides and feeling like they were within reach. I even landed a few to fakie on a low ledge in an abandoned car lot. Then, in 2000, I tore my ACL and spent a year recovering, never regaining that lost confidence.
The last real attempt to learn backside tailslides was about a decade ago. After a month of consistent practice and near successes, I slipped out, slammed into the ground, and fractured my thumb and bruised my chin, both shoulders, my testicles, hips, knees, and ankle. That put me off for a good ten years, it’s safe to say.
A front boardslide showcasing a different skateboarding trick from the same skater
Me front boardsliding in 2000 / photo: gillespie
The Pandemic Plan
When the COVID-19 pandemic hit in March, and the world came to a halt, I decided that I would focus on learning backside tailslides before life returned to normal.
At the time, we didn’t know when that would be, and honestly, we still don’t. I knew that I would be skating alone for a while, allowing me to practice without the fear of embarrassing myself. It also gave me something concrete to focus on amidst the frightening uncertainty of the pandemic in New York City.
Like everyone else, my wife, Rosie, and I were confined to our apartment, trying to keep things light for our five-year-old son, Fred, while obsessively following the news for updates.
Adding to the difficulty, we were new to NYC, having moved from New Zealand just a few months before. The exciting prospect of exploring the city was replaced with a sense of isolation that couldn’t be shaken by casual conversations with strangers.
During this time, I was distracted by the fantasy of the backside tailslide. I visualized doing it while lying in bed and spent countless hours researching it online.
Animated GIF showing the skater attempting a backside tailslide
I followed the @bstails Instagram account, analyzing every post for clues; I watched every YouTube tutorial and wrote down motivational tips on my phone (“crouch, approach with open shoulders, pop, then watch tail”). I revisited my favorite skaters and observed the new generation. I would sneak out after dinner and practice for an hour or two at a nearby curb. Yet, I returned home feeling no closer to success.
There was no real reason why I couldn’t do it. I believe that I built up mental barriers, and deep down, I didn’t think I was good enough. Much of my solo sessions involved summoning enough courage to just hop onto the curb in the back tail position. Once I got into the position, I would try them over and over until my vision blurred. It was like swinging in the dark.
There were a few close calls.
About a month ago, after a solid 30 minutes of convincing myself I was comfortable, I managed to get into one that slid a bit. After a few more tries, I slipped out and grazed my elbow. Within ten more attempts, I rolled away. The footage was less impressive than I imagined. It wasn’t really a tailslide, more of a quick skid, and the execution was a little strange. But it was, undeniably, sort of a backside tailslide.
A trick begins from the moment you push off; your approach shapes the outcome. This is why skating with friends always brings out the best in your skating; your confidence grows as you feed off each other’s energy. There’s always that split-second before you pop, though, where you’re on your own. You need to convince yourself that you can do it, that everything will be okay. If you believe you’ll land the trick, you probably will. But if you allow doubt to creep in, you’re likely to fail.
Another animated GIF showing a different angle of the skater attempting the trick
The Unfinished Chapter
During the long days of homeschooling my son, I sometimes felt like I had a breakthrough. I could almost feel myself learning the trick mentally. Later that evening, I would test my latest theory at the curb, only to be confronted by my own ineptitude. I would keep trying for hours, sometimes convincing myself that I was getting closer, but it never fully clicked. Even though I knew what I needed to do, I just couldn’t do it.
I wondered if I had waited too long. After 30 years of skating, my skills felt rusty, and my fear of falling was too great. The memories of past failures and injuries haunted every attempt, preventing me from fully committing. Perhaps this was the end of the road?
Eventually, when the weather improved, I simply gave up.
Backside tailslides were too frustrating, and I was tired of struggling. I chose to focus on tricks that came more naturally, telling myself that was a more intuitive way to skate. Still, it bothered me. Seemingly every barista at the local 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 served as a reminder of how incredibly difficult skateboarding is, and yet, it offered an escape from the rest of my life.
I might not have learned my dream trick, but I had become a better skater in the process. I learned new tricks, improved the ones I already knew, and became less afraid to step outside my comfort zone. Skateboarding rewarded my persistence, just not in the way I had hoped.
Animated GIF of the skater attempting the backside tailslide, highlighting the final moments
Words by: Max Olijnyk
