1) Murder
There are many types of murder and most are uncool. First degree murder is serious enough to be cool but it requires premeditation. Being cool means being spontaneous. Planning your crimes detracts from that. Manslaughter sounds like it would be cool on the strength of slaughter alone, but it’s actually just murdering someone by accident. Even though effortlessness is a hallmark of being cool, manslaughter is more about bungling your way into a murder by mistake. Uncool. So, obviously, a single murder is out. How about being a serial killer? Sure, the media often gives serial killers cool nicknames like “Son Of Sam” or “Zodiac” but this can just as easily backfire. What if you get stuck with a nickname like “The (Place Where You’re From) (Way You Did The Murders)”? Or worse “The (River You Dumped Bodies In) Killer”? Generic and uncool.
If you absolutely must murder, second degree is the safest way to go. It’s unplanned but still deliberate, which shows you’ve got a nonchalant attitude about things but you’re not to be messed with when things go down. Very cool.
2) Larceny
Larceny is so close to being cool. There are two types. Petty larceny may as well not even be a crime at all. To “commit” petty larceny, you only have to steal a small knick-knack or tchotchke. Imagine explaining to your cellmates that you’re in jail for stealing a trinket from an old lady (presumably). In addition to the initial embarrassment you’ll suffer when the other inmates laugh at the uncoolness of your crime, you’ll also be subject to daily beatings for it. That may be a good recipe for an emotionally detached vigilante style of coolness in the future when you’re hunting down your former tormentors, but for now, you’re just the uncool guy getting beaten up every day.
If you need to commit larceny then grand larceny is the gold standard. It’s much more exclusive and practically requires you to steal famous works of art or 99.9% pure gold bars to even begin to hit the threshold. The looming threat of not crossing the line enough and being taken down for a mere petty larceny ups the cool factor even more. Still, the danger of being taken down before you can steal enough and being hauled in for petty larceny makes larceny an extremely risky crime. Commit at your own peril.
3) Pickpocketing
Pickpocketing couldn’t be more uncool. It relies totally on randomness. Gambling isn’t cool. If the person you’re trying to steal from even has pockets, you’re flailing around in the dark, hoping that the thing you pull out will end up being a large diamond and not a poisonous snake. Well guess what. It was a snake. And you got bit. There’s nothing less cool than rolling on the floor, foaming at the mouth, desperately begging the person you just unsuccessfully tried to pickpocket, to suck the venom out of your wound.
Instead, try a heist. A suit, sunglasses, a sick machine gun, hostages. Extremely cool. Just make sure you don’t get stuck as the driver or you’ll end up waiting in the car the entire heist. Then you’ll have to listen to everyone talk about how cool everything was and you’ll have nothing to contribute except the songs you listened to on the radio while you waited. Which were very uncool. Adam Levine? Yikes.
4) All Misdemeanors
Misdemeanors are 100% uncool. Why waste your time with jaywalking and speeding when the chances of the SWAT team coming out and a huge standoff occurring is effectively zero? Crimes that carry serious consequences are the fastest route to coolness. You’re never going to get sentenced to death in the electric chair and get the chance to have your last meal be a cigarette, then have your last words be “let’s do this”, by littering.
5) Identity Theft
Stealing someone’s identity is tantamount to admitting that your own identity isn’t all that cool. Even if you manage to steal the identity of a cool person, you’ll probably mess it up and revert back to your original, uncool self, ruining a perfectly good cool identity in the process. What’s more likely is that you’ll pretend to be Phil, a guy whose credit card number you found while rummaging around in a trash can, so you can steal a set of mixing bowls off Amazon. But is it even stealing? You’re PAYING FOR IT. Maximum uncool.
Even worse, a similar crime exists where you impersonate a police officer. All the uncoolness of identity theft with the added uncoolness of being an authority figure. How are you going to scrape together some semblance of cool after that? Defy your own authority? This crime shouldn’t be done if you have any aspirations of coolness. Period. Stick to stealing cool items like Formula One cars, rare animal eggs and expensive antique rugs.
6) Ponzi Scheme
Crimes that rely on lying are uncool. A truly cool person always tells the truth with a sense of detachment and lack of concern for the consequences. A Ponzi scheme forces you to make up a backstory about a company that doesn’t exist to essentially beg for money. Begging is not cool. Not only that, a Ponzi scheme is already named after someone, so you’ll forever be in the shadow of a cooler person no matter how good you are at doing them.
A mugging is a much better choice. Walk up to someone and demand they give you money. Direct. Cool. None of the degrading “I can make lots of money for you. But, like, can you please give me some money first because I don’t have any money?” conversations that come along with a Ponzi scheme.
7) Arson
Fire is very cool and standing on a hill lit only by a distant blaze as the camera slow-zooms in on your dark, dead eyes is extremely cool. So why is arson so uncool? It’s just too physically demanding. You’ll be sweaty and disheveled, covered in soot. Your hair will be all out of place. Not only that, you’ll have to lug a heavy gas can around in one of your hands, instead of putting both your hands deep in your pockets where no one can see them (the coolest way to keep your hands). At least you’ll already have a match around for lighting your cigarettes. You are smoking, right? That’s just free cool points.
Arson should be used sparingly, to cover up other, more cool crimes. If the first thing people mention about your crime spree is the arson, you’re not on the path to coolness.