OK, so a lot can go wrong. But maybe nothing is worse than when the celebrity's troubles have a cruel, ironic connection to the product they're endorsing, turning your multimillion dollar ad campaign into an exercise in unintentional hilarity. We're talking about...

Really, can anything go wrong with a celebrity endorsement? OK, other than their latest movie/album/TV show turning into a flop. Or them getting caught on camera beating a hooker while wearing your clothing line.

5 Eric Clapton and Michelob

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Way back in 1987, Anheuser-Busch launched their "The Night Belongs to Michelob" campaign, a series of commercials involving popular rock and roll artists of the day. However the first couple of ads featured such stars as Steve Winwood and Phil Collins, two accomplished, albeit mind-numbingly boring musicians. Sensing they needed to take a new direction, Anheuser-Busch went out and recruited a giant in the music industry: Eric Fucking Clapton.

The commercial itself, although dated, is still pretty damned cool. It's got all your necessary rock and roll cliches, from the smoky club to the hot chicks (with big ass 80s hair) to the hip band and to top it all off, Clapton. Check it out here.

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The Problem:

Clapton, like virtually all musicians, had a bit of a drug problem (which he overcame), a fact known to just about everyone... minus the shithead ad execs at Anheuser-Busch. Either that or they did know and just were too stoned themselves to ask any follow up questions like "Are you clean and sober now Mr. Clapton?"

If they had they probably would've avoided the painful sting of irony. Right around the time Clapton's commercial was released, he decided to come clean... literally. Clapton fessed up that he was currently seeking treatment at a detox facility... for alcoholism.

The Fallout:

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Upon finding out that the centerpiece to their multimillion dollar ad campaign was in rehab trying to liberate himself of imaginary bugs, Anheuser-Busch promptly terminated the contract. They wanted an image of carefree people happily drinking in a smoky bar, damn it! Not of some guy responsibly seeking help from professionals when he realizes he has a problem!

These days, Anheuser-Busch has learned their lesson, stopped pretending beer is part of some kind of imaginary rock star lifestyle and now claims Michelob will turn you into a top athlete instead.