Most of the time, contextual advertising can be extremely beneficial in targeting online marketing campaigns. And then there’s these times. These contextual ads missed the mark by a mile and kept going, displaying ads that were wildly inappropriate, yet hilarious.

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For the Single Women, Dummy


Johann Hari may be missing out, but hopefully thie contextual ad will help him see the light. There it is, just waiting to plant a seed in Hari’s mind. Some religions may seem oppressive, until you mingle in the singles scene with them.

Fire Sale at Universal


This was not a great day to visit the Entertainment Capital of L.A., no matter how enticing the logo and ad may seem. The contextual ad touts the theme park on the same page as a live video of a raging fire there. Who’s game for the real life version of Backdraft?

Melted Away


This is just wrong. On an MSNBC page featuring the story of the first U.S. face transplant patient’s before and after photos — and neither are pretty — a beauty product ad exclaims, “My Wrinkes Melted Away.” Nice. This patient’s wrinkles also melted away, without the aid of any wrinkle creams.

Grill Like an Expert


When this sad news item appeared, no one could really be expected to smile while reading it. However, this inappropriate contextual ad on the page made it difficult not to at least smirk. We’re glad these monsters are in prison and hope nobody got any bright ideas by clicking the charcoal banner above the story.

Doping Can Help!


This contextual ad is irony to the highest order. As news of the former U.S. Postal doctor’s reaffirmation of doping claims broke, Lance Armstrong sat on the sidebar inquiring about your energy level. Doping? Who, me?

Fembots Rule


How awesome would it be to have a fembot as president? We may never know, but this contextual ad seems to be taunting poor Hillary for crying on the campaign trail. Fembots never get emotional, they don’t whine or complain and let’s face it, even the ugliest one is hotter than Hillary.

The Decision Was Made


Looks like this ad arrived a little too late to help the heartbroken Briton who sold his whole life after a breakup. However, maybe this thoughtful contextual ad will help the next Sad Sack or Debbie Downer from making the same foolish decision.

Former Cellmates?


Oh Google, is there anything you can’t do? After seeing you identify registered sex offenders on MySpace, I was amazed. Remember kids, Google has more dirt on you than Santa. These guys look so proud of themselves. Bastards.

Lose Weight Without Dieting


Eating disorders are no joke, but this misplaced contextual ad is a riot. Of course you can lose weight without dieting, just do what the kitty is doing after every meal. You can never be too rich or too thin.

Pitching a Tent


This is seriously awkward. The guy on the left is, um, pitching a tent, while the ad on the sidebar advertises great deals on camping equipment. While this contextual ad should be perfect for the subject matter on the page, a raging erection steals all the attention.

Killer Deal


This print ad for a “Killer Value”, appearing opposite of a tragic murder story is the ultimate in poor taste. A bot or algorithm can’t be blamed here, someone actually chose this ad placement.

Love Her or Hate Her?


As Matt Damon criticized and condemned Sarah Palin, she appeared to the right of him smiling. This was an unfortunate waste of ad space, as few Palin supporters would have actually watched the video.

Suggestive Contextual Advertising


This goes a little too far, doesn’t it? The contextual ad seems to suggest that our president is brain damaged. No worries though, there’s a lawyer standing by to help. How convenient.

More Coffee?


Go ahead, enjoy a second cup of coffee. The best part of waking up is Folgers in your cup, and a top news story on the Internet indicating coffee could trigger a heart attack in some people. We’re pretty sure you’re not one of them. Drink up.

You Might Want to Postpone Your Trip


If you’re lucky enough to win a mini-vacation in Greece, you might want to hold up on planning the trip. This gorgeous ad appeared in stark contrast to a news story about riots and violence in paradise.

Oh Yeah, That’s Humane


Stop animal cruelty. Not since “Shake That Bear” have we seen such an appallingly funny hunter/bear combo. This guy is using an AKA 47 off the back deck, apparently to shoot a bear.

Women Drivers


This real-life contextual advertisement above a urinal might not be a total fail. True, it is promising bargain rates for women drivers up there, but all is not lost if he’s the one who does the shopping around for insurance. Yeah, right. It’s a fail.

Peacefully Protesting This Ad Placement


The ad here seems to match the site, until you actually read it. The English Defence League, which peacefully protest against militant Islam, must have been horrified to see the International Muslim Matrimonial site advertised on their site.

Don’t Count Him Out Yet


Don’t count Steve Jobs out just yet. Despite his health problems, he will never be obsolete. He’s Steve Jobs.

Win a Bottle of Courvoisier XO


On one hand, the Guardian is reporting a call for a complete ban on any alcohol promotions or advertising. On the other, it’s running this sweet contest to win a bottle of Courvoisier XD.

Cellphone Death Unlikely


Whew, it’s a good thing it wasn’t the cell phone that killed this dude because that Samsung Blast looks sweet. Now that we pretty much know that cell phone didn’t cause the death, we can go shop at T Mobile.

Toddler Dating Site


Most kids aren’t allowed to date until they are in their teens. However, this contextual ad for Sarah Beeny’s Dating Site wants to start them off early. The ad appeared on the bottom of a video geared towards young children.

Black Is Beautiful


If I’m looking for a primarily black theme or a skin, really, that’s all I’m looking for — no hidden agenda. This suggestive ad assumes you’re looking for a bit more.