Some celebrity endorsements make perfect sense. For instance, if a famous basketball player were to get paid to vouch for anything, that anything should probably be basketball shoes. Even years after his third and presumably final retirement, Michael Jordan will forever be aligned with Nike. Their relationship was as symbiotic as any in the advertising industry, propelling the shoe manufacturer to the top of the market and reinforcing its chief spokesman as the most marketable athlete in the world.

SEE: When Celebrity Endorsements Don't Work

But other endorsements aren't exactly an artful marriage of pitchman and product. Jordan himself later plugged everything from long-distance phone service to underwear, as if he's somehow a definitive authority on either. Still other endorsements make even less sense. Some celebrities fail to reinforce the product's benefits, while others are about the last people on earth you'd want touting your product. Here are just a few of the questionable, ironic and inappropriate sponsorships of recent vintage.

Perhaps the most famous commercial spokesperson in history, ironic or otherwise, was Michael Jackson. Pepsi sponsored the King of Pop's 1984 tour, and in return Jackson and his brothers cut several TV commercials for the cola giant. The most infamous of those commercials, of course, never aired in its original format. It's the one that involved Jackson igniting, and which found its way into advertising lore. Jackson did appear in several other, less flammable commercials over the next few years, becoming the face of the No. 2 soda maker. But what's remarkable about this particular alliance between pitchman and product is that Michael Jackson went on record, multiple times, as admitting that he didn't particularly care for Pepsi and would never be filmed drinking it.

Pepsi knew this going in, and didn't care. The company believed, wisely, that being associated with a wildly popular and charismatic entertainer was more important than that entertainer's own opinion of its soda. For every multi-platinum recording artist who didn't drink Pepsi, there were millions of viewers who would. And that's a trade-off Pepsi gladly took.

For other products, with smaller reach than Pepsi, a more targeted approach is critical. Take Rogaine, which was and remains a technological breakthrough. As the slogan stated at the time, the medication was "the only product scientifically proven to regrow hair." But given that Rogaine's market consists almost entirely of self-conscious men uncomfortable about their appearance, it wasn't easy to find a celebrity spokesman. Parent company Johnson & Johnson needed someone who was not only confident in his masculinity, but unashamed of his desire to reverse his baldness.

Enter 6' 9", 265-pound hunter, fisherman, future first-ballot basketball Hall of Famer and all-around man's man Karl Malone. The Utah Jazz legend did a series of print ads and TV spots for Rogaine starting in 1997, not merely for Rogaine but for its extra-strength version. "The Mailman" had been losing hair throughout his professional career, and was willing to attach his face and his pate to a product that promised to reverse the process.

It didn't, and Malone didn't seem to care. By 2000, the only hair you'd find on Malone's head was his trademark mustache and perhaps a few days of beard growth.

A bald ex-spokesman for a hair restorer might be incongruous, but that's nothing compared to two car commercials that debuted during this year's Super Bowl, each featuring a driver who killed people while behind the wheel.

Honda ran a commercial promoting its CR-V, starring actor Matthew Broderick. That's the same Matthew Broderick who in 1987 allegedly drove the wrong way on an Irish country road killing a mother and daughter. If you view the long-form version of the commercial, you'll notice its star failing to signal a lane change at the :50 mark.

Whatever benchmark the Honda commercial set for dubious taste on Super Bowl Sunday, Kia tried to raise the bar later in the game. The manufacturer introduced its latest Optima model with an expensive conceptual spot loaded with celebrities – including Adriana Lima and Chuck Liddell, with musical accompaniment from Mötley Crüe.

The commercial features its driving protagonist nodding and exchanging knowing glances with singer Vince Neil, who in 1984 got behind the wheel of his De Tomaso Pantera while inebriated.

Doing 65 mph in a 25 mph zone, with a blood-alcohol level twice the legal limit, Neil crashed and killed his passenger. He also hit an oncoming car, inflicting brain damage and rendering her comatose for three weeks. Her passenger also suffered damaged brain. The Kia commercial first aired in February 2012, which is five years after Neil's second drunk-driving arrest, and a mere 18 months after yet another.

The Bottom Line
There's a lesson inherent here. If you're going to use someone famous to pitch your product, think safety first. "Inoffensive" is a positive attribute in advertising, and with good reason. Jerry Seinfeld might not be the most apt fit for Acura, nor Terry Crews for Old Spice, but it's unlikely that either company will end up regretting its choice of pitchman. Our examples on this list weren't so fortunate.

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