Before I got fired I used to tell my students that bad choices make for good stories. Maybe what I should’ve said is that bad choices make for trouble, which makes for good stories. If you think about it even a little, almost every story has a troublemaker making it go, so obviously the list of greats is large. Don Quixote, Huck Finn, Holden Caulfield, Dean Moriarty, Raoul Duke, Alex in A Clockwork Orange … Bartleby, even, who’s maybe not the most obvious choice, given his politeness, but c’mon: a guy who calmly declines to do as he’s told, until he dies. “I would prefer not to.” And I would prefer not to have to narrow it down to just 10 because, frankly, I’m terrified of that comments section below. Everybody’s going to have an opinion, as they should.

So I’m going to rule-bend here – this is about making trouble, after all – and give you my top 10 under-appreciated literary troublemakers, in the hope that I can introduce you to a few you’ll love as much I do.

1. The unnamed narrator in Henchmen by Marisa Matarazzo

You know that fiery, sickening feeling you get when you have a terrible but also great idea? This story, like so many in Matarazzo’s criminally obscure collection Drenched, tells you exactly what happens when those ideas are followed through. The narrator of Henchmen sets out to murder Kelly Green, the CEO of Target, and from there on it’s just about the most fun I’ve had reading in years. Take, for example, this description of a date in a bar: “I watch Tom’s hands fondle the deck of cards while the Three-Whiskey Gazelle bounds across the soft dirt path of my mind. Its coat afire in the smoky reds of a setting sun, muscles shifting gracefully beneath its hide. Trailing after it like a kite on a short string is a sign reading GO AHEAD AND FUCK HIM! I sigh.”

2. Guy Grand in The Magic Christian by Terry Southern

A hilarious billionaire determines to prove that there is nothing so awful that someone won’t do it for money. Whether it’s paying parking officers enormous amounts of money to eat the tickets, bribing an actor on a live TV show to deviate from the script, or buying a prestigious advertising firm just to install a pygmy as the president – it’s a book so funny and irreverent it led to Stanley Kubrick hiring Southern for Dr Strangelove.

3. The unnamed narrator in Letters to Wendy’s by Joe Wenderoth

OK, maybe this dude is more troubled than troublemaker, but man is his trouble contagious – the best kind. The entire book is comprised of dated entries written on Wendy’s customer-comment cards: Tell us about your visit. We care! Well, this maniac takes the fast-food chain up on its offer, and does exactly that, almost every day. The result is by turns hilarious, bizarre, tragic and disturbing, tracing roughly a year in the life of a guy obsessed with sex, death, consumerism and, well … burgers.

4. Phillip Liebowitz in Murderers by Leonard Michaels

I’m listing Liebowitz as the troublemaker here because he’s the narrator who declares – while recounting a day from his childhood – that he wanted “proximity to darkness, strangeness. Who doesn’t?” But really it could be any of the four kids in this story, who scale a tenement water tower to watch a rabbi and his bald wife have sex. Weighing in at just six and a half pages, it measures up to that other masterpiece about a troublemaking Jewish kid on a roof, Philip Roth’s The Conversion of the Jews. I’ll take Michaels any day.

5. Aunt Bernie in Sea Oak by George Saunders

This one was extra-tough, as there’s a hilarious, tragic, over-zealous, hyper-violent troublemaker at the heart of just about every Saunders story I can think of. And I can think of a few: the crazed, over-zealous, hyper-violent Vietnam vet Samuel from Civilwarland in Bad Decline; the crazed, over-zealous, hyper-violent Uncle Matt from The Red Bow; the crazed, over-zealous, hyper-violent Roger from Adams (a particularly brilliant, typically hilarious political allegory for George W Bush’s pre-emptive strike policy – just take the S off Adams, move it up front: ta-da!). But in the end, I have to go with dear old, dead old Aunt Bernie from Sea Oak. After dying of shock during a home invasion, she comes back from the dead a few days later with a renewed urgency and shows us – as so many Saunders’ stories do – that love plus fear can, and too often does, add up to aggression.

6. Fred in A Fan’s Notes by Frederick Exley

This “fictional memoir” opens with our recently divorced hero experiencing what he thinks is a heart attack, but is really just the result of a weekend of “foodless, nearly heroic drinking”. Exley then goes on to tragicomically explore the dark heart of sports fandom: the fear of remaining a spectator in life. It’s certainly a timely theme in our celebrity-obsessed culture, but never mind all that, and just enjoy as Exley troublemakes his way through years of addiction, psych wards, a failed marriage (to a woman named Patience), high-school English classrooms, faculty meetings, and just about everywhere else too. It’s the best!

7. Djarf Fairhair in Everything Ravaged, Everything Burned by Wells Tower

Speaking of spectators, this story – set during Viking times – is both brutal and funny, thanks to the detached narration of Harald, who’s pretty much over the whole rape-and-pillage racket. Of course the real star here is the troublemaker du jour, Djarf Fairhair, the “boss of the ship and a fool for warfare”. Whether it’s berserking with broadaxes or using a severed leg as a club, he puts on quite a show. And if you want to know what a blood eagle is – and trust me, you both do and don’t – you’re just going to have to read it.

8. Bobby Allen Bird in Saguaro by Carson Mell

One day, down in New Orleans, I ended up at the apartment of one of my sister’s yogi friends where – in an idiotic attempt to bed her – I beelined straight for her bookshelf and ridiculed things I’d only half read. She eventually got tired of listening to me, grabbed a book off the bottom shelf, and said something like, “You probably haven’t read this – it’s self-published – but you might like it.” Self-published? I thought. This should be good. Thing is, it’s better-than-good. Way better, and from the very first sentence: “When I was twelve years old I was best friends with a baby.” Fun, fast and voice-driven, Saguaro chronicles the life of rock legend Bobby Allen Bird as he recounts his struggles with barbiturates, dangerous women, fist fights with Bob Dylan, a cruise for satanists and a comeback, often while wearing his favorite colour: pink. If you like your troublemakers to be of the expectation-confounding variety, Bobby Bird’s your man. As for that yogi girl, she didn’t sleep with me, but as consolation I got to keep the book. Putting that in the win column.

9. Arthur “Duke” Wolff in The Duke of Deception by Geoffrey Wolff

A beautiful, emotionally complicated memoir told with incredible insight and generosity as Geoffrey Wolff attempts to explain his father – a conman who scammed employers, car salesmen, wives, his own son and, like, everybody. But don’t let me ruin it with vague descriptions and the threats of experiencing feelings. This Duke guy – from the outside, anyway – troublemakes with the best of them, and it’s more than a little fun to go along for the ride. A finalist for the Pulitzer prize in 1980; Wolff got robbed.

10. Georgie in Emergency by Denis Johnson

The narrator of Denis Johnson’s Jesus’ Son – only ever referred to as “Fuckhead” – is a likely choice for the most make-you-laugh-and-break-your-heart troublemaker in history. But I’m going to go ahead and throw my hat in the ring with the even bigger-hearted, pill-and-scene stealing, invisible-blood-mopping, shoelace untied-est hospital orderly ever, Georgie, from “Emergency”. How could you not love a guy who recklessly yanks the knife out of the face of an ER patient, runs over a pregnant rabbit, sleeps in his truck on the side of the road during a blizzard and maybe but probably doesn’t help an awol soldier get to Canada, and all in just under 16 pages? As the man himself puts it: “Jesus. Wow, oh boy, perfect.”

• Matt Sumell’s novel Making Nice is published by Harvill Secker.