How to Write the Perfect Cover Letter

I suck at cover letters.

There are several things in life that I am terrible at, and "writing cover letters" is up there, nestled snugly in between "pole dancing" and "seductive horse whispering". On this blog, I write like the jaded, sassy roommate you had in college who smoked clove cigarettes and spent a whole lot of time reading underground blogs about the 'man'. The moment I'm asked to produce a cover letter, however, I turn into a sad, garbled robot, capable only of spitting out mangled chunks of text that list my former jobs and generously overuse the term "excellent time management". The fact that I've ever been hired without holding an employer at gunpoint is as baffling as it is miraculous.

"Yes, you may contact my previous employer."

Unfortunately for me and all potential employers in my area, the time has come for me to find my first real, adult job while I save up money for graduate school, and I've been forced to hone my sad cover letter skills in a hurry. I've learned a lot from the job hunting process, and I'd like to use my newfound cover letter expertise to help my lovely blog readers. So if you're struggling to find a job and you want to upgrade to a sure-fire cover letter, pay careful attention to:

The Greeting

Letters generally have to be addressed to somebody. Cover letters are rarely sealed in bottles and set adrift in the ocean in the hopes that a passing fisherman might find work for you. You need to put some kind of greeting at the top of your letter, and ideally, that greeting should be addressed to the person whom you're hoping will make the grievous mistake of hiring you. Even a pimply sixteen-year-old hunting for his first job pouring cooking fat into the arteries of a nation knows better than to open with something impersonal like "To Whom It May Concern" or "Dear Corporate Overlords of Burger King". It's lazy, and it tells the potential employer that you didn't give enough of a shit to do even five minutes of basic Googling to find out which weary, world-battered employee would be setting eyes on your application. So what should you use instead? Their name, right?


Unless, of course, their names happens to be Beezow Doo-Doo Zopittybop-Bop-Bop.

We live in a job market that's more crowded than ever, and when you're up against two hundred other interchangeable Bachelor of Arts holders with no job experience, it's crucial that you stand out. Any moron can figure out that the hiring manager is named "Cynthia McSnickerdoodle" and slap a "Dear Ms. Snickerdoodle" at the top of the letter. That shows no creativity. Your greeting is your chance to make an unforgettable first impression, and demonstrate to the employer that you're a pretty bitchin' person they'd like to chill with at the office. And so with that in mind, you should put some effort into your greeting. Don't say "Dear Mrs. Jones". Say "To the finest bitch at TD Bank". Don't say "ATTN: Human Resources". Say "Greetings, Inferior Earthling Life Form". Don't say "Dear Mr. Washington". Say "Yo, what's good, homeskillet?".

Not to be confused with 'awayskillet'. 

Other examples of eye-catching greetings include:

  • Dear Chucklefuck
  • Mr. Potter, Our New Celebrity
  • Your Highness
  • Duuuuuuuuuuuuuuuude
  • Dear Chuck (I know your name isn't Chuck, but is it cool if I call you Chuck? Thought so.)
  • Yo
An eye-catching greeting tells employers up front that you're brave and you think outside the box. It also tells them that yes, you're going to be the reason they have to amend their company's drug screening and company refrigerator policies, but that's a small price to pay for someone with your creative mind. 

The Introduction

Every good cover letter must start with a brief introduction that explains the reason you're writing, ostensibly so that your local car dealership can quickly sort out job applications from the untold piles of fan mail they receive every day. Every cover letter therefore essentially starts off with a sentence that says "I need a fucking job", and every single way you could possibly phrase that sentiment politely makes you sound like an extraterrestrial who has only recently landed on Earth and is still struggling to learn our ways. "I am writing to apply for the position of Horse Masturbator as posted on Craigslist" makes you sound like you've got such a large stick up your ass that Jim Henson wants to cast you in a movie (or he would, if he hadn't died twenty-five years ago), and "I am excited to offer my application for the position of Butthole Bleacher" is the kind of hollow sentiment that tells the world you haven't felt joy since 1998. To a potential employer, you instantly seem like the kind of schmuk who'd wear khakis to work on casual Fridays and write memos reminding everyone not to exceed their maximum allotment of staples. And no one wants to work with a staple Nazi.

Or any kind of Nazi, really. 

Once again, it's crucial to stand out from the crowd. This is a great place to make an impassioned plea - sure, we all need money because we've got rent to pay and groceries to buy and bulk-sized packages of communion wafers to order from Amazon, but what makes you especially desperate for this job? Consider the following examples:

"Yo man, I'm really in deep with some guys, if you know what I'm saying, and they're runnin' out of patience pretty quick. I got two weeks to come up with the money, man, or they'll be puttin' my ass on ice. You'd really be doing me a solid by giving me this job."

"Please, sir, take pity on a wretched woman. I have six hungry children to feed, and it's been nearly four years since their father was lost at sea. Each night, I light a candle in the window to guide his safe return, but I fear that my hope is for naught, and that ruin is upon us. We've long since run out of money. The children sleep under a dirty tarp behind the Arby's, but I fear it's the best I can provide. Every day, I am forced to take the baby with me to beg outside the book drop at the public library, because I fear the other children will eat him in my absence, just to survive. Please, sir, choose me for the position of Administrative Assistant. We shall all be lost if you do not."

"You want to look at huge tits. I want to have huge tits. Huge tits cost money. You would pay me money. Let's work something out."

"To be honest, dude, I'm pretty much just applying because I need money for black tar heroin. Like, yeah, there are probably some bills and stuff that I should be taking care of, but the minute I walk in looking like a tweaked-out Jack Skellington, you're gonna figure out that I'm not here to make payments on my 2001 Honda Accord. So hire me, before I shank an old lady to death just to root through her pocket lint for change."

Telling the employer that you want the job just isn't enough. Everyone wants the job. Telling the employer that there will be hideous consequences for innocent people if you don't get the job is the sort of opener that makes employers sit up and pay attention. Possibly along with the police.

Your Qualifications

Of course, you need some qualifications before an employer can consider giving you an interview. Even if you can prove that an orphanage for blind children will plunge into a volcano if you aren't awarded the assistant manager position at your local Dairy Queen, you can't expect the monarch of cow fluids to give you a job if you can't scream at apathetic high school children and blend candy bars into soft serve with reckless abandon. The key to an impressive letter is pointing out how all your past work history and prison education courses fit perfectly with the requirements for the job - or at least, you're going to make it sound like they do.

"Experienced in engineering, construction, and creative thinking."

Unless you're a bored HR manager who enjoys posting your own job on and applying for it over and over again, you're never going to find a job that perfectly matches the set of skills you have. Yeah, maybe you have three years of experience as a pizza chef, but your local pizza place is actually a front for an elaborate drug operation, and they want at least six months of drug muling "or equivalent experience" before they'll give you a shot. Which means you have two options. You can run out and spend the next six months creeping around a back alley with a sandwich baggie of cocaine up your ass. Or you can take a look at your past work history, pick something that looks close enough, and stretch the truth until they hire you.

"You don't even want to know where these have been."

That might look a whole lot like lying, but outright fabrications are a bad idea. If your cover letter claims you were the stone-cold, meth-dealing pizza lord of 101st street, and they ask for a reference from your fictional distributer named Rico, you're pretty much fucked. If, however, you argue that your old job selling extended warranties at Staples had all the deception and soullessness of drug dealing, you might have a case. Learning how to spin your past experiences into perfect cover letters is an art form that takes time to master, but I can start you out with some basic examples to get you started:

Your job posting mentions that a PhD in electrical engineering is required to do this job. Now, while I may not have that, exactly, or any formal education in electrical engineering, I would like to draw your attention to the cashier job I held at my local Reddi Mart from 2007 - 2009. The electronic cash register had a loose connection or something inside it, and it would crap out all the time until you jiggled the power cord just right. I was the only one who ever got the hang of it, and my manager, Debrah, used to call me all the time when I wasn't on shift to talk her through it. So I figure that I've pretty much got this electrical engineering thing down pat.

I noticed that you're looking for someone with extensive sales and customer service experience - someone who knows how to put on a smile and go the extra mile for the customer. Well, rest assured, after more than twelve years of being trapped in a loveless farce of a marriage, offering service to complete fucking idiots is what I do best. I may not have worked in sales before, but if I can wake up every morning and choke down the vomit that arises every time I have to look at my husband, you can bet your suited behinds that I can trick your customers into thinking I give a shit about their shopping experience. You want me to push extended warranties? I push that fat bastard into going to work every morning so he can pay for the three kids I forced him to give me to fill the crushing void inside me - I can convince some old bag that her toaster's going to crap out unless she forks over an extra thirty bucks.

When you put out a call for a new CEO, you were probably hoping to get applications from people with things like 'fancy degrees' and 'experience running a company' and 'the slightest clue how businesses even work'. But let me assure you, my seven solid years of unemployment makes me a far better fit for the position than any experienced CEO. For one, let's talk about dress style. Everyone else who applied probably wears a suit every day, which you might think is a good thing, right? Oh, so wrong. Steve Jobs wore a turtleneck and mom jeans every day, and they made like, at least seven and a half movies about him. If I start showing up to press conferences in my threadbare pajama bottoms and stained undershirts, I'm betting they'll make at least nine movies about me. On a similar note, I'll be the ultimate scapegoat that your company needs. If everything goes well, you get the credit for recognizing an unqualified genius. If everything goes wrong, well, no fucking wonder, you hired an unemployed idiot for a CEO. Either way, it's win-win. 

Showing a potential employer exactly how your unique skills and background fit their job posting can make the difference between landing your dream job and looking on in sadness as the local 7/11 burns down in an attempt to destroy your resume forever. But sometimes, showing that you're a good fit isn't enough. After all, who wants to hire some asshole who's a perfect fit for the job, but doesn't give a shit about the company? That's why you have to:

Do Your Homework

Every company or employer wants to know that you at least made an attempt to Google them before you threw an application on the pile. After all, you might be the most qualified nurse on the planet, but if you're Jesus' #1 fan and you take a job at a Planned Parenthood without stopping to Google what they'll all about, it's probably not going to work out. Likewise, if you're thinking about joining the Mafia because you like opera and fancy suits, you might want to run that through the search engine of your choice before you tell your cousin Vinny that you're in.

Handy Hint: the first few years are a whole lot less of this, and a whole lot more waddling around downtown Montreal with a plastic baggy up your ass. 

As of the year 2015, we're all stuck in a job situation where everyone knows that your only hope of escaping unemployment is to fire out applications like a human blizzard made of resumes and desperation. The catch is that you physically do not have time to lovingly slave over each cover letter like you're tending a summer garden, but employers will not hire you if it looks like you sent out the same cover letter to every similar job posting in the greater metropolitan area. The secret to avoiding this is to include a sentence or two that shows the employer you did your research. It could even be something as simple as the following examples:

While digging through the dumpster behind your building the other day, I came across several receipts for store-bought cupcakes. Everyone knows that store-bought cupcakes are disgusting, and I would happily provide homemade ones for every office birthday if you hired me. 

I went through the Facebook accounts of every single member of your staff, and I think you'd better put up some new job listings, because I'm pretty sure that bitch Janice in HR is sleeping with that manwhore Jake from Accounting, right behind his wife Melissa's back, and when that shit hits the fan, I'm pretty sure one or both of them is toast. On a related note, I would be happy to fill either position when the time comes. 

I Googled your company, and you appear to be some sort of pizza place. I enjoy pizza. I often put it in my face. Let's work together.

Adding in that little personal touch to disguise the fact that you wrote this cover letter in a blind panic on the toilet because you've got 400 other jobs to apply to if you want to have even the slightest hope of making rent this month can really make all the difference. And with that out of the way, you're all ready for:

The Closing

Well, you're almost done. You've got a killer opening and a personalized introduction. You've explained why you want the job, why you're best for the job, and you've shown the initiative to do at least four seconds of research on their company prior to handing in your application. The only thing left to do is seal the deal with a killer closing.

No, not literally.

If your reserves of creativity are all tapped out by this point in the cover letter-writing process, allow me to give you some suggestions:

  • Peace out, bitches
  • See you at the office!
  • Ryan Seacrest, out.
  • So, yeah, that's pretty much it. 
  • Fare thee well.
Happy job hunting!

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