Will Funny Get You the Freelance Writing Job?

Back in my early freelance writing days, I felt being clever and amusing in my cover letter gave me an edge over other freelance writers applying for the same thing.

It didn’t.

If I learned one thing, it’s that freelance writing clients only want to see funny if funny is called for. All other times they want to see professionalism. I also learned that no one laughs harder at my jokes than me. In other words, I’m not necessarily as funny as I think I am and it could be the same way for you.

These are quotes from real cover letters. Tell me if you would hire any of these funny freelance writers for your project:

  • “What are you waiting for, f*cking hire me already.”
  • “I don’t suck so you won’t suck.”
  • “You can hire any old writer for your sh*t, or you can hire me.” (Deb’s note: Careful there, Skippy. You have convince me that you’re worthy of my sh*t)
  • “A writer, a priest and a rabbi walked into a bar…” (Deb’s note: This one had me intrigued but the writer didn’t include the joke, only the opening line.)
  • “Who’s the best writer of the bunch that’s great for you and me…M-I-C-H-E-L-Leee” (Deb’s note: Oh yes she did.)
  • “Hey you…yes, you!” (Deb’s note: Well who else would you be talking to in an email to me?)
  • “Show me the money!” (Deb’s note: Don’t you think we should make it past the cover letter first?
  • My words aren’t boring like yours, they sing. I’ll sing you higher sales and better playing clients. Don’t you want that song in your heart.? (Deb’s note: Really, no.)

Here’s the thing. People who hire writers enjoy funny, and we enjoy clever. We also enjoy writers that breaks out of the cookie cutter mold. We don’t want elevator pitches, we want to know why you’re the best person for the gig. If you’re truly funny, you can let that shine through. Not everyone can pull this off in a cover letter or job application.  My advice to wannabe funny people is to let a second pair of eyes read your query first. If others aren’t laughing, you probably have a clunker on your hand.






10 responses
  1. Steph Auteri Avatar

    I was in complete disagreement with you when I first started reading this post. After all, I learned back in college that all resumes look the same, and that it’s a unique cover letter that gets you noticed. I took the advice to heart, and have always been a nice mix of casual and professional in my cover letters, letting my personality shine through. In fact, I’ve been in to a number of interviews where hiring managers have told me: “We loved your cover letter! That’s why we had to bring you in!” I’ve received similar feedback from a number of editors. So, will funny get you hired? Totally!

    Then I read the examples of “funny” in your post, and I started cringing. And I had to admit: Yes. There is a line.

    Oh my lord. 🙂
    .-= Steph Auteri´s last blog ..My New Web Platform Has Launched! =-.

  2. Jack Busch Avatar

    Being funny is a bit like dancing. If you can do it well, then do it. If you can’t, then for everyone’s sake, get off the dance floor before you hurt yourself or someone else.

    I’ve actually put out a call for “humorous” material, hoping for some good articles in the spirit of The Onion. But what I got instead was pure madness. And I think that’s the problem. People confuse humor (transcending conventions in a surprising and amusing way) with insanity or rudeness (breaking conventions in a sociopathic way). And the examples you pulled out all come off as insanely rude.

    I think there’s some inherent incompatibility between cover letters and humor. The best humor – in my opinion – is self-deprecating or satirical. And since you won’t really get far by selling yourself short (imagine Woody Allen at a job interview), these would be comic applicants resort to boastful diatribes against the would-be employer, which, for obvious reasons, is way worse.

    I never attempt humorous cover letters myself. Humor is too subjective to work most of the time and we’re all a little bit less funny than we think we are. There are rare opportunities to have a laugh at no one’s expense, but I think your time is better spent crafting an excellent cover letter and revising your resume than workshopping your standup material.

    With all that being said, I did end up hiring someone who’s email subject read: “Pick me, Pick me!” But she has other redeeming qualities, too.

  3. David Delony Avatar

    It depends on what you’re applying for. If you’re applying for a humor Web site, for example, try to get the people reading your cover letter to wet themselves. If you’re a technical writer, it’s best to avoid that kind of thing.

  4. Mike Fook Avatar


    If I’m in the right mood I can pull off a few wicked funny lines that I can laugh about for 10 minutes. This is why I routinely wait before sending email to anyone where money might be a factor either now, or in the future, about 15 minutes.

    Money – there’s no sense joking around about it when it’s your money.
    .-= Mike Fook´s last blog ..Thai Black Book – Ultimate Survival Guide for Thailand Visitors or Expats =-.

  5. Roberta Rosenberg Avatar

    I think you can write an entertaining cover letter – clever, personable, a style that clearly communicates you – without being funny. (I discovered that by accident when, after 5 attempts at a letter to ‘showcase my writing talents’, I just wrote on-point from the heart.)

    As others have pointed out, funny is a very subjective enterprise. As I learned in my one year of comedic stylings many years ago – you gotta play the room. Good advice for well, just about everything!
    .-= Roberta Rosenberg´s last blog ..Links for 2006-07-29 [del.icio.us] =-.

  6. Jeanne Avatar

    There’s funny…and then there’s painful. Or rude. Anyone who would use a swear word in a professional business letter would automatically get tossed out (by me as a hiring manager). I can’t believe anyone would do that. Yet there it is.

    I’d love to see more examples of unique, original cover letters…after 20 years, I still struggle with them!

  7. Karen Swim Avatar

    Deb, ROFL! I laughed but for all the wrong reasons! Yikes, and no I would not hire any of the writers. I also advise against swearing in a cover letter, instant turn off. Not sure why people even do this on social media platforms. Part of my business is career marketing and branding. You can stand out by allowing your marketing materials to have personality but personality does not mean being crude, or treating your prospective client / employer like a buddy. Thanks for sharing these examples and helping us all to ensure that we not making these mistakes. BTW, I think I’m funny too but I’m pretty sure it’s just my opinion.
    .-= Karen Swim´s last blog ..Brand Autopsy: GreenBox is Marketing Done Right =-.

  8. Freddie Jaye Avatar
    Freddie Jaye

    “Dying is easy. Comedy is hard.”

    “Comedy, like brain surgery, is best left to a professional.”

    Unless it’s someone I know well, or I can use mild humor as a common-bonding agent with someone (having a ‘honeydew” list for example), I stay away from it.

    Humor is just too subjective. I think “The Honeymooners” TV shows are hysterical, even though I’ve seen them all a couple dozen times. My wife and daughter just sit there stone-faced.

    Be straightforward. Be professional. Nothing’s worse than someone who doesn’t “get” your joke.

  9. P.S. Jones Avatar

    Oh these were so not funny. Besides, funny is relative to the audience’s personality, intellect and frame of mind. Somebody facing an inbox full of resumes and a job to get done probably isn’t looking to sit through your comedy set. They just want to know if you can do the job and why you’re better than everyone else.
    .-= P.S. Jones´s last blog ..What Sex and the City Gets Wrong About Being a Writer =-.

  10. CJ Sandifer Avatar

    “We also enjoy writers that breaks out of the cookie cutter mold”

    –Should read: “We also enjoy writers that break out of the cookie cutter mold”

    Need a proofwriter? I’m about as meticulous as they come.

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