The first example of a celebrity endorsing a product came in 1850 when flamboyant showman P.T. Barnum imported the Swedish opera singer Jenny Lind and arranged for her name and likeness to be associated with a wide range of products including clothing, furniture and pianos.

Into the 20th century, the increased power of print and broadcast media and a greater public fixation on celebrities let more companies recruit performers and athletes as spokespersons for their brands.

Sometimes, very popular celebrities spokespersons overstay their welcome or get tripped up by extraordinary circumstances. General Electric (NYSE:GE) dropped Ronald Reagan as its spokesperson when his personal appearances on behalf of the company veered away from product hype to political messaging; a similar situation derailed Anita Bryant's long run as the celebrity spokesperson for Florida's orange juice industry. O.J. Simpson and Bill Cosby were popular favorites for their respective long-running advertisements for Hertz Global Holdings' (OTC:HTZGQ) rental car service and Kraft Heinz Company's (NASDAQ:KHC) Jell-O puddings, respectively, but today they are not quite beloved by the public.

But on occasion, companies pick the wrong celebrities to promote their brands. Here is a quintet of stars whose salesmanship efforts went hopelessly awry, with astonishing results.

Madonna for Pepsi. In March 1989, Madonna was the hottest star in the music industry when PepsiCo Inc. (NASDAQ:PEP) signed her to appear in a television commercial. The spot, dubbed “Make a Wish,” served the dual purpose of promoting Pepsi while offering a preview of the singer’s upcoming hit song, “Like a Prayer.”

The two-minute commercial aired during an episode of “The Cosby Show” and was a relatively benign affair, intercutting scenes from the “Like a Prayer” music video with quick shots of the Pepsi product and logo. However, Madonna coyly told Rolling Stone that “the treatment for the video is a lot more controversial. It’s probably going to touch a lot of nerves in a lot of people.”

And how! The “Like a Prayer” music video was released the day after the commercial aired, complete with raw and visceral blending of sexual and religious imagery that created seismic outrage stretching from the Bible Belt — the right-wing American Family Association called for a PepsiCo boycott — to the Vatican — Pope John Paul II demanded the music video be banned from Italian television.

While PepsiCo had nothing to do with the music video, the company quickly distanced itself from Madonna and refused to show the commercial again. Madonna, who was paid $5 million for the commercial, has yet to appear in another soft drink advertisement.

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Sharon Stone for Christian Dior. Sharon Stone gained a reputation for steaming up the big screen in movies like “Basic Instinct” and “Casino,” but who knew that she had the power to boil the world’s most populous country without even trying?

Stone was a celebrity spokesperson for the luxury goods retailer Christian Dior (OTC:CHDRF) in May 2008 when an earthquake rocked the southwestern corner of China, resulting in the deaths of more than 68,000 people. Far from the disaster — the red carpet of the Cannes Film Festival in France, to be precise — Stone was asked about the earthquake by a reporter.

"I'm not happy about the way the Chinese are treating the Tibetans because I don't think anyone should be unkind to anyone else," she said. "I've been concerned about how should we deal with the Olympics, because they are not being nice to the Dalai Lama, who is a good friend of mine. And then this earthquake and all this stuff happened, and then I thought, is that karma? When you're not nice that the bad things happen to you?"

As any longtime Benzinga reader will recall, the Chinese government is a wee bit sensitive when it comes to be criticized from outside its country. The Chinese state news agency Xinhua labeled Stone a "public enemy of all mankind" while cinemas in China and Hong Kong banned her films. Dior took the hint, dropping Stone from its advertising and offering heartfelt apologies for having anything to do with her. Stone would also apologize and Dior kept her in its ad campaigns except for the Chinese market.

Alicia Keys for Blackberry. Alicia Keys is celebrated for making beautiful music, but she was significantly off-key during her brief stint as the celebrity face of BlackBerry Limited (NYSE:BB).

In Keys’ case, the company gave her a title (global creative director) and a salary in January 2013 amid the much-ballyhooed release of its BlackBerry 10. Unfortunately, she got off on the worst possible foot by getting caught tweeting out the message “Started from the bottom now were here!" via her Twitter (NYSE:TWTR) for iPhone app.

But rather than offer a giggly “oopsie,” Keys deleted the tweet and then posted a new message insisting that she was hacked, adding a speculation that Drake was somehow involved. Keys, who had previously developed an iOS app that let fans add her image to their own photographs, quickly found her role within the company was limited to appearances at business functions and waving the company’s products during her concert performances.

She parted ways with BlackBerry one year later as the company sought to refocus its business strategies away from star-struck consumers into more B2B-oriented enterprise solutions.

Lebron James for Samsung. The concept of thinking before tweeting was absent from basketball great Lebron James’ mind on March 12, 2014, when he tweeted out: “My phone just erased everything I had in it and rebooted. One of the sickest feelings I've ever had in my life!!!”

There was actually a bigger problem for James than his mobile device’s disruptive behavior. The device’s manufacturer, Samsung Electronics Co. Ltd. (OTC:SSNLF), had signed him to a $100 million endorsement deal — and this was not the kind of endorsement they were expecting.

The tweet quickly generated 518 retweets and 1,108 favorites before James deleted it — but, of course, nothing is ever truly deleted from the internet. James attempted to make amends by tweeting how we was able to recover his data, although the following year he goofed again when news reports surfaced that he presented his Cavaliers teammates with watches from Samsung’s rival Apple Inc. (NASDAQ:AAPL).

Mercifully for James, his corporate benefactors displayed Job-worthy patience amid his repeated bumbling.

Jerry Seinfeld for Microsoft. Ten years after Jerry Seinfeld bid adieu to his sitcom, the funnyman turned up on the small screen in a pair of commercials for Microsoft (NASDAQ:MSFT) that generated bafflement from nearly everyone who saw them.

One commercial, running a somewhat lengthy 90 seconds, finds Seinfeld in a shopping mall shoe store where he helps Microsoft chieftain Bill Gates in his footwear purchasing. The unlikely pair engage in non-sequitur remarks reminiscent of “Seinfeld” — except they’re not funny.

The only high-tech aspect involves Seinfeld speculating on making edible computers that are “moist and chewy like cakes” — and when the comic asks the tech giant for a signal that such a product is being developed, Gates gives his tushy a little shake.

The next commercial, running a rather epic four-and-a-half minutes, finds Seinfeld and Gates living with a dysfunctional suburban family. There is a great deal of interfamily bickering and the pair are eventually evicted, dragging their suitcases down the street to a horizon with Seinfeld babbling about animals using computers.

Microsoft paid Seinfeld $10 million for his time, but found itself fighting off criticism from the advertising industry for the effort. The company attempted to pull a George Costanza with a statement that said, “The answer, in the classic Seinfeld sense of the word, is nothing.”

Ultimately, it pulled the ads completely and the company rushed out traditional commercials with normal running times and catchier messaging — not that there’s anything wrong with that.

(Sharon Stone photo courtesy Alexis / Flickr Creative Commons.)

Original publication: 2021-05-16

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