The Funniest Cover Letters Ever Sent (And Why They Didn’t Work)

Ah, the cover letter. That curious piece of parchment that’s meant to showcase your unique brilliance but often ends up reading like the diary of a madman.

It’s the handshake before the handshake, the professional equivalent of “Hey, how you doin’?” But while some people see it as their moment to shine, others treat it like an opportunity to demonstrate precisely why they shouldn’t be allowed near a keyboard.

You see, in the world of job applications, the cover letter can be your best friend or your worst enemy. When done well, it’s like the opening act of a great show, setting the stage for what’s to come. But when done badly, it’s like a 90-minute bagpipe solo at a rock concert - baffling, unwelcome, and more than a little painful.

Here, for your amusement, are some of the funniest cover letters ever sent - and a look at why, despite their charm, they didn’t quite hit the mark.

1. The Overly Honest Approach

Imagine, if you will, an applicant who decided that honesty was the best policy. Their cover letter opened with:

"I am applying for this job because I need money to pay my rent. I don’t know much about marketing, but I’m a quick learner."

Now, while we can all appreciate the candid nature of this application, it didn’t quite scream “qualified professional.”

Being honest about your motives is one thing, but perhaps, just perhaps, a sprinkle of enthusiasm for the job itself wouldn’t have gone amiss.

2. The Shakespearean Sonnet

There’s a fine line between creativity and outright madness, and one applicant decided to blur that line with a cover letter written entirely in iambic pentameter.

"To whom it may concern, I write today, With hope that I may find a brighter way. For in this job, my skills shall bloom anew, And bring forth all that I desire to do."

While this certainly got a few laughs, it also left hiring managers wondering if they were reading a job application or an audition for the local theatre.

Sometimes, it’s best to leave the poetry to the poets.

3. The Overconfident Candidate

Confidence is key, they say. But there’s confidence, and then there’s what one might call delusion.

One cover letter boldly declared:

"I am the best candidate you will ever find for this job. If you don’t hire me, it’ll be the biggest mistake of your life."

And while we appreciate someone who knows their worth, hiring managers tend to prefer candidates who focus on what they can bring to the role, not how lost they’ll be without them.

4. The Unintentional Comedian

Humour can be a great way to stand out, but it’s a high-risk, high-reward strategy. One applicant took it too far with:

"I’m applying for this job because, frankly, my current boss is a nightmare. I need a new job before I end up on a true crime podcast."

While it might have gotten a chuckle, it’s not quite the professional tone most companies are looking for.

A little levity is fine, but it’s best to leave the murderous undertones out of your job application.

5. The Bizarre Skillset

Highlighting your skills is essential, but one applicant took this to a new level:

"I am an expert juggler and can recite the entire script of the first Harry Potter movie from memory. I believe these skills make me uniquely qualified."

While impressive, the connection between these talents and the marketing position they were applying for was, at best, tenuous.

It’s always best to focus on skills relevant to the job at hand.

6. The Copy-Paste Disaster

We’ve all been there, trying to save time by using a template. But one applicant forgot to update the placeholders:

"Dear [Hiring Manager], I am very excited to apply for the [Job Title] position at [Company Name]."

It’s a classic example of a little too much automation and not enough attention to detail.

Remember, a personal touch goes a long way.

7. The Excessively Formal Letter

In an attempt to sound professional, one applicant wrote:

"Kind Sir or Madam, it is with the utmost veneration and esteem that I humbly submit to you this missive of intent."

While it’s nice to be polite, there’s such a thing as overdoing it.

A simple, courteous tone is often more effective than writing like you’ve been transported from the 19th century.

8. The List of Demands

One particularly ambitious candidate used their cover letter to list their demands:

"I require a corner office, a company car, and at least six weeks of vacation."

While knowing what you want is admirable, it’s best to wait until you’re actually offered the job before making these kinds of requests.

Negotiation is a fine art - one best not attempted before you’ve even secured an interview.

Need Help Finding Applicants with Better Cover Letters?

If these examples have made you question the state of your own recruitment process, fear not. At Coburg Banks, we specialise in finding candidates who can write a cover letter without making you question their sanity.

So, if you’re tired of sifting through bizarre applications and want to get in touch with real talent, we’re here to help.