• by Mary C. Long , Columnist, October 27, 2016

In our world of tiny attention spans, the art of well-placed, well-timed, catchy marketing to attract buyers has become the norm. And with it comes some hilarious screw-ups.

Can you name that last snazzy new item you purchased from Amazon’s “Deal of the Day” – or just from online, in general? Bet there are a few things among those purchase that were more impulse than necessity, sitting idly in your house, unused and neglected. Some you may even repurchase, forgetting you already have a solar-powered, camouflage camping fan tucked away in your closet. Retailers win those rounds. But when they lose, their sloppiness is noteworthy: Wrong market, bad timing, misplaced hashtags, over-the-top or cultural misunderstandings, you name it (beyond what I just did).

So, with the holiday season quickly approaching, and retailers scrambling to finish flyers and commercials to lure our wallets and credit cards into their stores, here are some of the “Best of the Worst” holiday marketing gone terribly, terribly wrong to help you feel a little less bitter about things:

1. Hanukkah Hum-Ho - 2015

What happens when an upscale department store runs a print ad, marketing a “humorous” Hanukkah? Nordstrom quickly pulled this sweater, part of Faux Real’s ‘Chai Maintenance’ line, off its racks, after customers protested on the store's Facebook page, saying the slogan was a slur and stereotype against Jewish women.

2. MLK the Surfer - 2011

What does a surf shop in Laguna Beach, Calif., do to drum up business in January? Crop Martin Luther King, Jr.’s image onto a surfer's body and offer a 20% discount on all black items in the store. Needless to say, this was an epic fail. Sometimes, we can all do with a little less creativity in our lives... .

3. Frightfully Tactless...2014

Thousands of customers took their outrage to Twitter when it was discovered that Walmart's link for plus-sized women's costumes led to a “fat girl costumes” section. While Walmart spent days apologizing for this mistake (or hack), let us remember that all businesses are ultimately responsible for their websites – the good, the bad, and the ugly.

4. Facebook Fail - 2013

This is where research is essential. The London Luton Airport used this picture to highlight safety, but a 6-year-old boy was killed onboard the plane pictured, which slid off a runway in Chicago in 2005. Their airport might be safe, but this tactless attempt at marketing certainly wasn’t.

5. Christmas Ball(s) - 2015 

Out with your best friend, enjoying a lavish holiday work party...she looks good...really good...go ahead, spike her eggnog...take her back to your place...it's consensual...really... what's the harm? Or so Bloomingdale's would have you believe. Somehow, no one caught this glaring invitation to date rape, until it was published in the department store's holiday catalog last year. After receiving complaints on Twitter, Bloomingdale's issued an apology.

6. Stocking Stuffer - 2007

Nothing says Merry Christmas like receiving a bottle of va-jay-jay fragranced perfume. What more is there to say?

7. Timing is Everything. - 2014

With the release of Season 1 of Sleepy Hollow, the execs at 20th Century Fox decided to create a series of ecards for the show's fan base. Sadly, they were publicized soon after American journalist Steven Sotloff was beheaded. The show's PR team quickly made the social media rounds to apologize for their ill-timed idea.

The list is far from comprehensive, but it speaks to three things:

• Something funny and clever can quickly turn into snarky and off-putting, given the wrong presentation – and it can then become part of your company’s branding, depending on how strongly you stand behind it. Take Kenneth Cole, for example. Using Cairo’s revolution to promote his new spring line was a jerk move, but he’s stood behind it and used similar tactics, successfully, since.

• Don’t run on auto-pilot: Just because an idea was created today, doesn’t mean it won’t be entirely inappropriate based on current events two weeks from now when it launches. Re-evaluate efforts before hitting “send” and listen to that little voice. If you worry it might be taken the wrong way, it will be. And auto-scheduling campaigns to launch is a death knell for a marketer, not to mention an amateur move.

• Prepare for fall-out: If you do hit send on something even remotely controversial, prepare for the internet overreaction that could potentially ensue and takes steps to frame the conversation before it gets started - or don’t launch the idea. The absolute worst thing you can do is to take a risk and then play victim when everything spins sideways. Not only do you look like a jerk, your intelligence and marketing savvy is questioned. And rightfully so.

Good luck this season!