The Art of the Devastating Insult

There is a fine line between delivering a light-hearted, laugh-inducing quip at someone’s expense and a devastating insult that creates hard feelings (and potential bruises). And it’s an easy one to inadvertently stray across. Trust me on this; I know what I’m talking about.

Even with natural wit, you have to work at your craft because the insult is an art form that takes practice. Typically, you don’t have time to think it out — you have to launch your insult while the opportunity is available. So, you need to develop a second nature for boundaries so you don’t end up in HR one day having an uncomfortable conversation about your future with the company.

My brother Kevin was a master of the quick insult. He’d roll in unexpectedly like a Mongol raider and *thpt thpt thpt* stick you full of verbal arrows that left you chuckling. Then he’d be on his way before you could truly fathom how thoroughly he’d just owned you.

Me, I consider myself more of a storyteller with routines polished over time, but back in junior high, I used to sling one-liners and insults like they were going out of style. It’s where I discovered a perfectly timed quip doesn’t always have a positive outcome.

Not built for brawling

Being a young teen and realizing I could make the cool kids laugh with my witticisms and well-timed put-downs became intoxicating; it was like discovering I had a superpower, but one that I overused. I gained a false sense of confidence. Being inexperienced, what I didn’t appreciate was the inherent danger in off-the-cuff quips and put-downs — you have to learn moderation and proper application. And you usually have to learn that the hard way.

Life in junior high for skinny kids like me could be nerve-racking. You never knew when some hulking teenager with a Magnum P.I. mustache and holding a grudge because he’d been held back in 9th grade three times might decide to stuff you into a garbage can. And boy, was I skinny. The kids called me Stick Man for a reason. (Another nickname they hung on me was Bones.)

The Land Manatee's 9th grade ID
My 9th grade ID. I was all Adam’s apple (hmm they got my middle initial wrong)

I’d always been skin and bones. When I was a kid in England and ran around in my Number 7 Kevin Keegan Liverpool football kit, my grandad used to call me Legs Eleven because my thin legs resembled two number ones. As he also put it, I had legs like two knitting pins. Entering ninth grade, I was fourteen and still rail thin. Tall and gangly for my age, I weighed maybe 115 pounds (52kg) after a heavy meal. Nature had not physically prepared me for the brutal rigors of junior high having bestowed upon me pencil-thin arms and a rib cage that resembled a xylophone. Which was unfortunate because my wisecracks sometimes attracted the attention of kids who solved annoying problems by punching them.

Ill-fated love

Anyway, one morning on the bus ride to school, this kid on the wrestling team had a group of us around him as he held court. We occupied several rows in the back third of the bus, just outside of stoner territory as weed and cigarette smoke wafted forward. Two days before, the wrestler had landed a girlfriend who I thought was a bit out of his league — not that he was hideous, it’s just his eyes were a little bulbous and heavy-lidded. But it looked like true love — every time I saw the new paramours they were attached at the hand like conjoined twins.

That morning on the bus, the wrestler surprised us by telling us he had dumped her, which seemed fast even by junior high standards. He pulled a note out written by his new ex and read it aloud for our entertainment. Being an empathetic person, this rubbed me the wrong way. Plus, I found his attitude to be cavalier considering that 95% of the boys at Fremont Junior High would have contemplated committing a felony to get a girlfriend. You don’t spurn the largess of the gods and then mock their gift.

Now, I didn’t know his ex-girlfriend, but I felt bad for her as he read her anguished words aloud and laughed. She pleaded with him to give their relationship another chance. She listed all the ways she would be good for him, including being there to support him in his athletic endeavors. Unfortunately, she referred to herself as his number one athletic supporter, which is also a name for the undergarment that supports and helps protect a male athlete’s genitals.

“That’s hilarious, man. She wants to be my jock strap and support my balls,” he said.

This got a raucous laugh from his primary audience of pubescent males and a few scornful glares from girls who maintained solidarity with his ex.

“A freaking jock strap hahaha! Why would she want to be my jock strap?” he asked.

man's athletic supporter and cup
Not the athletic supporter she planned on being.

“Maybe it’s because you’re a big dick.”

Wow, who said that? I wondered.

You did, dumbass, replied my brain.

The quip had popped out of my mouth so quickly it caught me by surprise before I had the chance to run it past headquarters for clearance.

It hung in the air, the perfect, crystal-clear note ringing out in a virtuoso performance. I couldn’t have timed it better as it arrived during a fortuitous lull in the ambient noise of student babble as the bus idled at a light, its engine at its quietest.

Everyone in earshot erupted into laughter, some gasping for air. Well, not everyone. As I reveled in my unexpected triumph for a microsecond, a pair of bulbous eyes locked onto mine.

A warning klaxon went off in my head as the wrestler stared at me as if he couldn’t process what had just happened. A penguin waddling down the aisle of the bus at that moment would have surprised him less. If possible, his froggish eyes bulged out even more than normal. In a sudden panic, I wondered if he’d let my impertinence slide because my battleship mouth had just written a check my rowboat ass couldn’t cash. But like an old-school warship sitting at the dock, it was just taking the wrestler a moment to build up steam and get underway as he stoked his internal boiler with combustible rage. As his face flushed crimson, it became pretty apparent the U.S.S. Ass Beating was preparing for action stations.

Uh oh…

He leveled a thick finger of doom at me. His dry voice offered no humor, just future pain.

“You are so dead.”

My stomach plunged in freefall as the kids around us hooted and oohed loudly as they smelled blood. The bus had transformed into the Roman Coliseum, and I’d just voluntarily thrown myself to the lions. Adrenalin flooded my body.

In the turbulent teenage world of male social dominance, I found myself in an awkward situation. Experts in juvenile behavior clinically refer to it as being in deep shit. I’d committed the cardinal sin of making an alpha male look foolish. Instinctively, we both knew he had to restore the natural order and that meant rebuying his credibility. And the only acceptable currency was pain. My pain.

A no-win situation

Scared, I went into survival mode as possible solutions flashed through my head but I had limited options. I could try to grovel my way out of it. And even though I had a lot of experience in that area, I had no guarantee it would succeed. My other option was to stand tall and fight him once we got to school (until he bent me into a pretzel). That had even less appeal. In theory, I knew karate. My parents, concerned about my weediness, had signed me up for Shotokan training a couple of years prior. Even though I’d mastered my katas with good technique, I had a tendency to fold like a deck chair when someone hit or kicked me when sparring. At heart, I was a martial arts movie fighter — all form and no contact. I lasted maybe 6 months and quit after I earned my yellow belt. (A rather appropriate color.)

The wrestler changed seats quickly to get closer to me, taking an open spot next to another kid. Skittish, I was already on the move. Disobeying the rule to stay seated, I scuttled way up front to take an open spot next to the bus’s resident weird kid, Hans. My adversary started to move up, but the bus driver happened to glance in his large mirror and bellowed at him to sit down.

Sweating the rest of the ride to school but dreading our arrival, I hoped that the wrestler wasn’t seriously contemplating kicking my butt.

“Hey Stickman,” he called out from mid-bus, his menacing words forcing their way over the sound of the engine. “Better get a scuba mask cause I’m shoving your head up your ass.”


Well, at least I knew where I stood.

There was a third option besides groveling and fighting, and I took it. When the bus stopped, I was ready. I hopped up and slithered my way past others to the front door and ran like a Kenyan. I did my best to disappear into the throng of students waiting for the first-period bell.

All day long, filled with anxiety, I scanned the horizon for trouble, ready to bolt. I didn’t have any classes with the wrestler, but that didn’t mean our paths wouldn’t cross unexpectedly between classroom buildings or while exchanging books in the claustrophobic confines of the outdoor locker cage. Lunch was a nightmare of constantly looking over my shoulder as I gobbled my food.

My main advantage was I already existed in a state of perpetual hyper-vigilance. Being a gawky kid in junior high was like being a Thompson gazelle on the Serengeti — something always wanted to fuck your day up. So I had learned to keep my head on a swivel and travel in relative safety with the migrating herd of students moving between classroom buildings. And run when I had to. Those instincts served me well that day.

Thompson gazelle
Who? Me? I didn’t say anything.

Time to pay the piper

Finally, the end of the school day arrived. I dreaded going to the buses gathered at the front of the school. It was just making the wrestler’s job easier — but I didn’t have any choice. Even thirst can force the wary Thompson gazelle to forgo caution and go drink at a crocodile-infested river.

As we waited for the buses, I nervously looked around, but the wrestler wasn’t present. Hope began to build when a teacher let us board our bus. I sat up front thinking I’d be okay for another day — and then the wrestler got on. He walked by without saying anything and sat down a few rows behind.

It was the longest and shortest ride home ever. The excruciating seconds ticked by as students joked and chatted, leaving my stomach a cauldron of bubbling acid. I could feel the wrestler’s cruel eyes boring into my back.

When the bus pulled up to our stop, I got off, but rather than running, I decided I had to end this one way or another. Stress had my eyes blinking out subliminal help messages in Morse code as the wrestler stepped off the bus. Before he could say anything, I started apologizing in machine-gun fashion and said I hadn’t meant to cut him down on purpose.

I expected an angry fist or for him to put me into a full Nelson or at least give me a wedgie, but he told me he wasn’t mad anymore. He even admitted my quip had been pretty funny — but added if I ever cut him down again, I would need that scuba mask.

Reprieved! A huge weight lifted off my shoulder and I walked home with a spring in my step.

Did I learn my lesson? Yes and no. My mouth continued to annoy others, sometimes when I hadn’t said anything objectionable, and occasionally get me in trouble. It got me chased, punched, pushed around, jabbed in the chest by a finger that felt like a piece of rebar, stuffed into a trash can once, and racked in the nuts numerous times.

All in all, it was a vital lesson about watching what I said and to whom. I learned I could say what I wanted, but my speech wasn’t free of consequences. Sometimes I was going to pay a price for a funny line — so it better be worth it.

And if they laughed, it was.

21 thoughts on “The Art of the Devastating Insult

  1. You always make me laugh, Sean.

    I’ve met a few masters of the quick insult in my life and wasn’t particularly impressed. Generally, I like to speak my mind about things but there’s sth I’ve always known – watching what I said and to whom. Sometimes it’s worth the trouble, other times, I figure – you better not open that mouth because the consequences would be irreparable.


    1. Sean D. Layton

      Glad I can get a chuckle, Bojana. Yes, you’re so right. In college and in my twenties, there were times where I wished I’d just stayed silent for sure. It took a while, but I’m far more judicious these days.


      1. Sean D. Layton

        Agreed. That’s one of the things I dislike about social media — it encourages people to put things out in the heat of the moment that they shouldn’t. That and anonymity on the Internet allows incivility to go unchecked.


  2. Lisa Porter Cordovana

    Awesome – you have such a way with words! I have no filter either, Sean. Neither does my daughter. I hear this gets worse with age! Lol


    1. Sean D. Layton

      Being a cute cheerleader in high school worked in your favor though ha ha Less chance of getting stuffed into a trash can. πŸ˜‰ . Glad you liked the post!


      1. When I taught high school/junior high one of my goals was to make school more bearable for the non-popular kids — I quickly learned you can only control your small slice of their day (and not even that every day) — and the rest is Lord of the Flies…


      2. Sean D. Layton

        Oh hell, I had a PE teacher who made his class Lord of the Flies. We used to play a game he devised called Slaughter Ball. The sadistic version of dodge ball.


  3. β€œA penguin waddling down the aisle of the bus at that moment would have surprised him less.” Crack me up! Middle school was truly the worst, infinitely worse than high school, I thought.
    What a great story, this was so much fun to read!


    1. Sean D. Layton

      Glad you enjoyed it. Yes, totally agree about the difference between junior high and high school. In fact, I assumed it was going to be worse so I decided I’d write a best-selling novel over the summer break after 9th grade so I could skip it.


    1. Sean D. Layton

      Thanks, Michelle, I’m glad you enjoyed it! Ive already got some practical advice from your site (and do I ever need it). πŸ˜‰


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