Marketing has come a long way in the last two centuries, but it’s hard to get people’s attention these days. Sometimes, you’ve got to do something big and outrageous and potentially dangerous, and sometimes, those things don’t always work out exactly the way you’d planned. Like employing a guerilla marketing firm to promote a cartoon movie and inadvertently causing a citywide panic (see previous post: “Innocent Ideas That Prompted Mass Hysteria.”)

With that in mind, here are a few of history’s better bad marketing moves. Feel free to file these under “It seemed like a good idea at the time.”

1. Sponsoring Headstones

Gaming companies are always pushing the bounds of bad taste in their products (Manhunt 2, anyone?), but in 2002, Acclaim Entertainment shocked the UK when it announced it would pay mourning families to place small billboards on their relatives’ headstones advertising the game Shadowman 2. The company thought it was an appropriate place to advertise the “dark, gory” game, which it billed as a “journey to the Deathside.” Acclaim later said the offer might “particularly interest poorer families.” The Church of England responded by saying they had a hard enough time dealing with those plastic flowers in graveyards, and by no account would it allow video game advertisement on headstones. End of story.

2. Chocolate Bombs

Back in the fall of 1926, a Berlin chocolate company made international headlines after police shut down their marketing campaign—because citizens were complaining of bruises. According to a contemporary AP article in the New York Times, the company had been sending up two planes every Sunday to bombard crowds of people with foil-wrapped chocolates from a height of about 100 feet. “The aerial gifts were particularly objectionable to bald-headed men, whose custom it is to stroll with heads uncovered on the theory that the sun’s rays stimulate the growth of hair. Mothers complained that children fighting for the prizes ruined their Sunday clothes.”

3. Snapple Sees Marketing Stunt Melt Away

You could see the logic here: What’s better than a popsicle on a hot day? Nothing. Just maybe not a 25-foot, 17.5 ton popsicle. Snapple found that out the hard way in 2005 when the company unveiled their gargantuan kiwi-strawberry popsicle in the middle of Times Square, which promptly started to melt in the 80-degree heat, losing a torrent of sticky kiwi-strawberry concentrate all over the streets.

4. Molson to College Kids: ‘Drink up!’

It’s not much of a secret that college and beer go together like, well, college and beer, but Molson brewing company found itself facing a whole poop-storm of controversy when it tried to capitalize on that fact. In 2007, the company launched an online marketing campaign targeting Canadian college kids, asking them to post their best party pictures on Facebook in a contest to determine Canada’s top party school. The grand prize was a spring break trip to Cancun for the winner and four friends.

Parents and school officials were not pleased. One school official plainly told The Globe and Mail he was disgusted, while others demanded that Molson axe the campaign, claiming it not only targeted underage drinkers, but also promoted irresponsible drinking in a big way. The winning photo, they reasoned, would have to be pretty outrageous to merit a trip to Cancun.

Molson, bowing to the pressure, pulled the campaign.

5. Escape Artist Turned Marketer Has Brush With Death

In 1990, magician-cum-marketer Jim McCafferty wanted to launch his marketing and brand consulting business with a big time attention-grabbing stunt—and nearly died in the process. The idea was that McCafferty, straitjacketed, would be locked in a metal cage, welded shut on all sides. The cage would then be hoisted by a crane 300 feet off the ground and McCafferty would have two minutes to get out of the straitjacket, out of the cage, and attach himself to a harness before the timer released the cage and it plummeted to the ground.

McCafferty got out of the straitjacket with little problem, but found himself stuck in the cage. With just 10 seconds left on the clock, he managed to scramble out and onto the roof. As he fumbled with the harness, the timer ran out, and the cage fell 60 feet before he was able to click in to the harness and arrest his fall. McCafferty was taken away by ambulance, suffering from first- and second-degree rope burns. All was not lost, however: The crowd loved the stunt, thinking that McCafferty’s brush with death was simply part of the act and McCafferty has gone on to run his successful million-dollar company.

6. Arrested for Vodafone

This would not be the first time anyone got naked in the name of advertisement, but it was certainly one of the few times anyone was arrested for it. In 2002, two brave young men raced across the rugby pitch during a match between New Zealand and Australia, clad in naught but the Vodafone logo. The two were caught, mid-streak, and escorted off the field by police. Vodafone later apologized for having “encouraged” the duo to do their naked run and later donated £30,000 to a nonprofit campaign to reduce sports injuries.

[Many thanks go to Entrepreneur magazine, whose compilation of PR stunts helped pad our list.]