Advertising has been the cornerstone of human commerce for as long as mankind has had branded products to sell. Archeologists believe the first such product was a caveman marital aid called the “hit on her” club. Since that clever caveman marketing campaign, advertising methods have evolved.

The greatest leap in this evolution came with the invention of the celebrity endorsement. As a whole celeb endorsements have been a winner. But there have been a couple of entirely inappropriate celebrity endorsements we thought should be highlighted.

1) James Dean promoting safe driving on the roads

The Advert:

Why it was a FAIL:

2) Olsen Twins Got Milk? Ad

The Advert:

Why it was a FAIL:
Any food or beverage advertising campaign the employs an anorexic celebrity is destined to fail.

3) Gary Glitter

The Advert

Why it was a FAIL:
OK granted this ad was made many years before Gary “I’m a child sex tourist” Glitter got busted in Vietnam. But still look at him, he looks like a pedo, he’s dipping his hand in cream and the ad contains the words “keep hold of young persons”…..*shudder*

4) Pope Leo XIII

The Advert:

Why it was a FAIL:
It’s not bad enough the Catholic Church has so many Irish priests. Now they are further encouraging alcoholism….FAIL!

5) Michael Jackson and Pepsi

The Advert:

Why it was a FAIL:
MJ was actually a great celebrity for Pepsi. The filming of the ad was where the FAIL occurred.

It also marked fire’s weakest moment in world flame history. Up until the filming of this commercial anything that went up in flames turned black. Paradoxically Michael started to turn white after this event….FAIL to both Pepsi and Fire!

6) Flintstones

The Advert:

Why it was a FAIL:
In the 60’s, things deemed abhorrent by modern standards were accepted as the norm. Shooting hippies on campuses and cigarette campaigns run by cartoon characters are two such examples. Modern day standards state that the Flintstones advert is totally unacceptable and hippies should only be shot with rubber bullets.

7) Martina Hingis and Sergio Tacchini

The Advert:

Why it was a FAIL:
At the time of Martina’s sponsorship with Sergio Tacchini, she was the biggest name in women’s tennis and brought a massive boost in the sales for Sergio Tacchini. So how can this be deemed a FAIL? A few years after endorsing the company she sued them on the grounds that their shoes weren’t tournament fit and were the sole cause of her career ending injuries….ouch!

This article was written by James Faust from TheLamest.com. If horrid endorsements and product fails are what strike your fancy, then check out America’s leading Product Fail blog, Would Not Buy This.