The Best Worst Idea You've Ever Had

It's a new year, which means people are looking back on last year and regretting stuff, telling themselves that they won't repeat the same mistakes this year and that they're going to be model citizens who will – by the end of February – probably end up on TV talking about ways to improve their community and other narcissistic bullshit.

Of course, those people are idiots and are mostly wrong. They're not going to change, they're just going to make the same resolutions the following year. And anyway, so what if you make a couple of bad decisions? Sometimes bad ideas can turn out to be the best thing ever. Then again, the best ideas in the moment can also turn out to be the worst. Here's a few stories where that's happened.

Illustrations by Sam Taylor. Follow him on Twitter @sptsam or visit his website at samtaylorillustrator.com.

HIGH ROLLER HINDSIGHT

At the beginning of my second year of university – aware of how easy it was to get by on very little money, as long as I had enough for ketamine and baked potatoes – and after a worryingly small quantity of pints, I had the fantastic idea of going down to the casino, finding the roulette table and putting my entire student loan on red. I think red was decided because my friend was wearing red trousers at the time and we were all ripping on him because the only people who wear red trousers are interminable douchebags who Like Facebook pages like "Shooting clays on the lash" and "That awkward moment when your shoes cost more than all of that homeless pleb's belongings."

Anyway, I won, which instantly doubled my bank balance. I didn't have any specific plans as to what I'd do if I won, but before I could really register my haul, that overwhelming feeling that you get when you find a tenner and realise that it's essentially free money washed over me. I realised the casino probably wasn't a great place to exercise that victimless lack of restraint, so took everyone I was with to the closest bar, bought three bottles of champagne and round after round of drinks.

A couple of hours in, when the pussies had scarpered off to get to bed before their lecture the next morning, or whatever, I headed to a cashpoint, withdrew £400 and charged towards a strip club with whoever was still hanging on. The next few hours are a complete haze. I have glimpses of trying to put a rolled-up 50 note in a stripper's arse, looking down to see a mixture of blood and sick all over my shoes, buying some crack, then smoking that crack with a man in a park (who I don't remember having a face) and trawling around the known prostitute area, alone, looking for a glamorous way to continue my temporary high-life.

I woke up the next morning – drenched in my own piss and crusted vomit – in the doorway of a chicken shop, with the owner nudging my stomach with the end of his boot. Dragging myself up, I skulked over to a cashpoint to grab some taxi money and found that I'd hit my maximum overdraft limit. Even once my winnings were transferred I was still hugely overdrawn, to the point that my next couple of months consisted of no ketamine and the green, sprouting potatoes I had left over from first year. But fuck it, there's no interest on student loans and – from what I can remember – I had a great night, so all was good in the world again.

SEXY DREAMS REALLY CAN COME TRUE

So, I'd been interning at a PR company for months. Unpaid, of course, because why would 11 hours of my time every single day be worth anything to a couple of private-schooled Surrey girls with Moleskine clipboards and a healthy sense of self-entitlement? I figured maybe I should have a crack at getting at least some kind of expenses out of it, though, because skipping the tube fare and stealing lunch every day was starting to turn me into a slightly more paranoid version of Howard Hughes after a vapouriser of whatever chemically-engineered skunk won the last Cannabis Cup.

I made a last ditch effort to set up a meeting with the reclusive – to the point of near-non-existent – boss, but that fell through twice, which gave me the motivation I'd been waiting for to sack off the job and hastily slide my way down to the bottom of the unemployment ladder. One thing that kept me going through that time was pornography. I dunno, there's just something warming about constantly orgasming alone in bed while all your flatmates are out slogging away at work. While browsing through one of my favourite adult websites, I stumbled across something called Tanya Tate's Casting Couch, which is – I suppose – an employment initiative, where Tanya, a Scouse pornstar living in LA, gives you the opportunity to sign up and have sex with her.

I noticed that she was planning on coming over to London and thought, 'Well, porn has always been my second profession of choice, maybe this could be my foot in the door' so decided to sign up. Whether it was because of my dazzlingly good looks or sublime personal statement, I have no idea, but I got the part. Freaking out slightly, I necked a Viagra – realising I'd never live it down if I choked on camera – and got to work. Funnily enough, you completely forget about the lights and cameras after a little while. I suppose the vaginas help. Long story short, because of that I'm flying out to LA in a couple of months to shoot my first professional scene. So anyone stuck in a dead-end internship, never give up hope – there's always being paid to put your dick in someone or have a dick be put in you on camera as a solid gold fall-back.

REVOLUTIONARY MISTAKE

You know when you're young and stupid and alcohol is still a novelty and you wear necklaces with weed leaves on them and make sure everyone at school sees your Che Guevara t-shirt on home-clothes day? Okay, so that was me ten years ago and I'm not afraid to admit it because this is the internet and you don't know what I look like so you can't take the piss out of me when you see me in public. Anyway, my friend and I got stupid drunk one day on a few stolen beers and a bottle of Armagnac from his dad's cupboard, and decided it would be a good idea to unleash our brewing anti-capitalist leanings like the junior cultural revolutionaries we were.

We made a banner that said, "Money can't buy you love. Don't fuel the pig empire," and headed off to climb on to the roof of what we thought was National Jean co. (because we were on an anti-sweatshop brigade at the time) but later turned out to be a Walgreen's, an American pharmaceuticals store, which I suppose still counts for something, but didn't mean anything to us at the time whatsoever. My friend brought tape, rope, a knife, a switch blade and a camera, so just about everything you'd need to kidnap and torture someone (the two blades already racking up a double felony in the state of Massachusetts). Oh, and a bunch of fireworks, which are also illegal in Massachusetts.

As soon as we reached the roof, the cops were called immediately and six cars and two fire trucks soon arrived and surrounded the building with guns drawn. It turned out we were on a roof connected to the Post Office, so we were accused of attempting to burgle a federal building. I had to go to juvenile court with my parents and the judge, upon hearing my parents' English accents, promised that he was going to "Show [us] that this is the best country in the world and that America's justice system is not one to be messed around with". I got eight hours of community service.

A SHITTY NIGHT

I was at a big house party in Brixton with a load of mates. As is usually the case with big house parties, we didn't know the people who owned the house or many of the people there outside of our little crew, but it was fine because everyone was wasted and nothing bad ever happens when people are wasted, right?

A few hours in, we'd gravitated towards the kitchen. One of my mates, Ryan, was leaning on the hob and unknowingly releasing a cloud of poisonous gas into the room, which obviously isn't good vibes. No one likes manslaughter at a house party. Luckily one of the guys who lived there realised and shouted at Ryan to get off the hob, which he mistook for fighting talk, angrily shouting at the guy to fuck off. Obviously confused and angered that this stranger was taking offence to him trying to save a room full of lives, the guy ran off and returned with a cricket bat, a bunch of his mates and told us we had to get out because "guys like [us] are nothing but trouble". That's clearly a lame thing to say, and very funny, so laughing the whole way out, we completely forgot we'd left Ryan's girlfriend alone, dancing in the living room.

On realising, we rushed back and looked through the window to find the guys holding her back and grinning at us maniacally, with the look in their eyes that only Fosters-swigging university rugby players with no idea they were technically holding someone hostage could have. Ryan flipped out and punched a hole through the window, slicing up half of his hand and sending blood all over the walls. I don't know if it was embarrassment or he suddenly decided that his girlfriend wasn't worth hurting his hand for, but he darted off almost instantly into the night.

The next two hours were spent trying to find him, repeatedly calling his phone and ringing around friends and hospitals to see if he'd pitched up anywhere. At around 5AM, just as we were beginning to presume him dead, Ryan stumbled through the door covered in blood and his own shit. Turns out he'd needed to relieve himself, so went to a graveyard, had a shit in a grave, got stuck in the grave and ended up repeatedly falling back into his own pile of faeces every time he tried to escape. Some bad ideas end up working out, this one really didn't.

HORSE PLAY

I'm a pretty nice guy all things considered, but I do have this weird predilection for being a complete dick when I feel like people aren't involving me in stuff. For example, one time I went to a cabin in the Scottish highlands with some friends for a weekend and they locked me outside because they knew it would piss me off. I then lost a screw, shit in my hands, smeared my shit all over my friend's car then drank some of my own piss. I don't know what I'm hoping to achieve when I go into these weird little rage blackouts, but out of the numerous times they've happened, nothing good has ever come of it.

Until a few months ago, when I was round my mate's house in the Suffolk countryside. It was the height of summer – that point where it doesn't get dark until like 10PM and the air smells really good the whole time – and we were having a barbecue. Everything was going well and I hadn't had an incident in months – something my friends were clearly aware of, because I noticed a rustling between them, before they all got up and sprinted through the French windows, locking me out and eagerly grabbing their phones, waiting for me to flip.

I was tempted, and I could feel the rage bubbling up, but instead I cracked a beer and swigged it down as fast as I could in an effort to keep my feelings locked under. Then I opened another beer, and another, and another, until my rage turned into this bizarre blend of confidence and carelessness. I think it's called "being drunk". Anyway, sauntering over towards my friends, I gave them the finger, turned on my heels and raced towards the neighbouring field, where I'd noticed a load of horses calmly grazing away.

I'd only been riding once before, so in retrospect this was probably a terrible idea, but I leaped up on to a horse bareback, beer in hand with the sun setting behind me, and started riding towards the closest town. I heard the cries of my friends, but what I did care? I was fucking Charlton Heston, riding off into the night towards whatever buxom beauty lay waiting for me in the nearest watering hole. Only – less than a minute in – once the horse picked up more pace than a gentle walk, I fell off violently, broke my shoulder, fractured my spine and ended up concussed in the hospital for the next three days. A word of advice: don't ride horses if you're drunk and have never ridden a horse before – it's not a good idea.

Illustrations by Sam Taylor. Follow him on Twitter @sptsam or visit his website at samtaylorillustrator.com.

More stories:

A Very Messy Christmas

The Very Worst Sex You've Ever Had

There's Nothing More Damaging Than School

A Party's Not a Party If You Don't Punch a Fish