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The Most Questionable Celebrity Endorsements of All Time

Updated: Jul 14, 2023By Emma VernerBusiness
This article originally appeared on Investing.com. It has been republished here with permission.
George Clooney ©Ray Tamarra/GC Images/Getty Images George Clooney ©Ray Tamarra/GC Images/Getty Images

Brands have long harnessed the power of celebrity to sell their wares, no matter what those products may be. While usually the tactic of employing famous faces to sell goods goes over like gangbusters, every once in a while the brands take big swings, which result in even bigger misses. 

From extremely insensitive ads in poor taste that happen to be for snack foods, to luxury watch endorsements gone wrong, many of the celebrities on this list deeply regret hitching their star to companies with poorly thought out commercial campaigns. Others still managed to sneak by with lucrative overseas Proctor & Gamble laundry detergent campaigns or made great money from hawking yogurt or adult diapers. 

1. Snoop Dogg for Hot Pockets

Year: 2012
Outcome: Mocked On The Internet

In 2012, Snoop Dogg, or Snoop Lion, as he wanted to be known at the time, appeared in a commercial for Hot Pockets, in which he performed his hit song “Drop It Like It’s Hot”. Instead of the usual lyrics, he swapped them out for words about the popular molten-hot microwavable snack. 

Snoop Dogg for Hot Pockets @laughingsquid / Pinterest.com Snoop Dogg for Hot Pockets @laughingsquid / Pinterest.com

The video went viral on the internet, but not for the right reasons. The rapper’s previously hardened public persona, having run with Los Angeles gangs, was instantaneously replaced with a goofy character peddling frozen meals. Whether or not the commercial actually helped sell more Hot Pockets is unknown. 

2. Jamie Lee Curtis for Activia

Year: 2008-2014
Outcome: Activia Paid Out $21 Million For False Claims

Jamie Lee Curtis took to Twitter to defend her decision to do the yogurt commercials for seven years, allowing her to make good money while being able to spend time with her husband and children. Unlike working on feature films, commercials allowed her to be flexible with her time. 

Jamie Lee Curtis for Activia @r/redscarepod / Reddit.com Jamie Lee Curtis for Activia @r/redscarepod / Reddit.com

Meanwhile, Activia was fending off the FTC because of false claims that the yogurt was “scientifically” and “clinically” proven to improve gut health and regulate digestion. Due to their misleading ads, they had to pay out a $21 million settlement in 2010, and tweak their commercials going forward. 

3. Charles Barkley for Weight Watchers

Year: 2012
Outcome: Barkley Let Slip That It’s A “Scam”

In a move that many thought would cause Charles Barkley to lose his Weight Watchers spokesman role, the former NBA player mistakenly let slip that he thought the whole sponsorship thing was a scam while he was wearing a microphone during a Miami Heat game. 

Charles Barkley for Weight Watchers @OldTakesExposed / Twitter.com Charles Barkley for Weight Watchers @OldTakesExposed / Twitter.com

Barkley meant that it felt too good to be true to get paid to lose weight, which he explained at length, not realizing he had a hot mic on. Luckily for the former basketball phenomenon, Weight Watchers had quite the sense of humor about the whole thing, not penalizing him for the slip-up. 

4. Ozzy Osbourne for I Can’t Believe It’s Not Butter

Year: 2006
Outcome: Proved The Wrong Point

In 2006, rocker Ozzy Osbourne starred in a commercial for popular margarine spread I Can’t Believe It’s Not Butter. The ad featured an Osbourne impersonator, attempting to poke fun at the idea that the butter replacement is great at impersonating the real thing. 

Ozzy Ozbourne for I can’t Believe It’s Not Butter @mincer11 / Twitter.com Ozzy Ozbourne for I can’t Believe It’s Not Butter @mincer11 / Twitter.com

Unfortunately, viewers took the commercial to mean the opposite thing, recognizing that no margarine replacement like I Can’t Believe… can take the place of butter, just like no celebrity impersonator can take the place of the real deal. While a fun concept, the ad didn’t accomplish what it set out to do. 

5. Madonna for Pepsi

Year: 1989
Outcome: Pepsi Pulled Ad After Madonna Released Music Video

In 1989, Pepsi paid Madonna a whopping $5 million to use her song “Like a Prayer” for their commercial. All seemed fine until the pop starlet released her scandalous music video the next day, which featured erotic imagery mixed with religious iconography. 

Madonna for Pepsi @cristianpalacio / Pinterest.com Madonna for Pepsi @cristianpalacio / Pinterest.com

Pepsi thought that the music video was far too racy for them to continue having the song associated with their brand, and so they chose to pull the ad entirely. To this day, Madonna hasn’t forgotten their move, posting a recent Instagram post with a can of Coca-Cola. 

6. Kim Kardashian for Charmin

Year: 2010
Outcome: Criticized For Selling Out

Kim Kardashian, the original celebrity famous for being famous, also managed to leverage her fame into an empire in the hundreds of millions, owing a significant part of that sum to her advertising efforts. While the starlet has done waist trainers and diet pills, she really went off the rails with her ads for Charmin. 

Kim Kardashian for Charmin @r/KUWTK / Reddit.com Kim Kardashian for Charmin @r/KUWTK / Reddit.com

The star appeared at the unveiling of public toilets sponsored by Charmin, put up in Times Square in 2010 for the holiday season, fully available to tourists. After doing the highly-publicized ribbon-cutting ceremony, fans realized there was pretty much nothing the reality star wouldn’t do to make a buck. 

7. Bob Dylan for Victoria’s Secret

Year: 2004
Outcome: Troubling Legacy

The older man appearing in a video full of scantily clad young women is enough to make this commercial unsavory, but adding in the fact that it’s none other than Bob Dylan adds extra layers to this problematic spot. The singing/songwriting legend has taken hard stances against selling out before, which makes this appearance particularly confusing.

Bob Dylan for Victoria's Secret @Ultramelodic / Youtube.com Bob Dylan for Victoria's Secret @Ultramelodic / Youtube.com

Not relating to his music or brand in any way, shape, or form, it’s hard to say what drove Dylan to appear in the spot. Once associated with the general countercultural movement, it certainly left fans with a poor taste in their mouths after watching Dylan’s ad for bras and panties. 

8. Penélope Cruz for Nintendo

Year: 2012
Outcome: Penelope Cruz Dons A Mario Costume

In an ad featuring Cruz and her sister Monica, which was no doubt a ploy from the gaming manufacturer to appeal to a wider audience, the two battle it out against each other on the newest portable console. 

Penélope Cruz for Nintendo @THRmag / Pinterest.com Penélope Cruz for Nintendo @THRmag / Pinterest.com

Penelope loses to her sister, and so she must uphold her half of the bet: wearing a full Mario costume, mustache and all, to the supermarket. The silly ad made waves, mostly because people were clamoring to see the gorgeous movie star dressed as the cartoon plumber. 

9. Malcolm McDowell for Lunchables

Year: 2015
Outcome: Criticized For Being “Too Self Aware”

In the Lunchables taco advertisement, Malcolm McDowell plays a teenager who is simultaneously out of touch with the kids of today. The commercial took a big swing, attempting to be self-aware, but was declared an even bigger miss, and an “embarrassment” by critics. 

Malcolm McDowell for Lunchables @Adweek / Twitter.com Malcolm McDowell for Lunchables @Adweek / Twitter.com

The silver-haired star should probably avoid Lunchables ads and stick to the silver screen, where appearances in films like A Clockwork Orange and Caligula earned him considerable critical acclaim. Most recently, McDowell has appeared in popular television series like Chicago Med and the reboot of Gossip Girl. 

10. Paris Hilton for Carl’s Jr.

Year: 2005
Outcome: Heavily Criticized for Overly-Sexual Ad 

Carl’s Jr. wasn’t shy about using sex appeal to sell their burgers, coming in hot with a television commercial featuring socialite Paris Hilton in a bikini soaping up a Bentley before taking a bite of one of their burgers. The sudsy car wash scene drew a lot of criticism for not relating to the quality of the burger at all. 

Paris Hilton for Carl's Jr. @aoljobs / Pinterest.com Paris Hilton for Carl's Jr. @aoljobs / Pinterest.com

While these days, advertisements that have nothing to do with the product they feature are nothing out of the ordinary, in 2005 the Paris Hilton for Carl’s Jr. ad created a big hubbub. Carl’s Jr. stood by the ad, which was certainly successful, keeping the fast-food chain’s name in the media for a long time. 

11. David Beckham for Brylcreem

Year: 1997
Outcome: Beckham Shaved His Head, Jeopardizing Money

In 1997, soccer star David Beckham was all the rage, frequently appearing on the glossy pages of tabloid magazines with his now-wife then-girlfriend Victoria “Posh Spice” Beckham. With long blonde hair at the time, he signed a six-million-dollar contract with Brylcreem to be the face of the hairstyling product company.

David Beckham for Brylcream ©s_bukley / Shutterstock.com David Beckham for Brylcream ©s_bukley / Shutterstock.com

Then, in 2000, with about a year left in the contract, Beckham emerged from a salon with his hair entirely buzzed off. While tabloids went to town with his new ‘do, insisting that he would lose his sponsorship, nothing of the sort actually happened. 

12. Jean-Claude Van Damme for Total Flex Home Gym

Year: 2011
Outcome: Sued For Publicly Disparaging Product

Belgian actor and martial artist Jean-Claude Van Damme got himself in hot water after he backed out of advertising for Total Flex Home Gym at the last minute, and then went on to trash talk the brand on his reality show Jean-Claude Van Damme: Behind Closed Doors.

Jean-Claude Van Damme for Total Flex Home Gym ©Mishakov Valery / Shutterstock.com Jean-Claude Van Damme for Total Flex Home Gym ©Mishakov Valery / Shutterstock.com

Owned by Thane International, the company cited damages of around $25 million after Van Damme apparently showed up to the infomercial shoot without having learned his lines or even trying to use the equipment. He then left on his lunch break after becoming frustrated with his inability to figure out the machine and quit the commercial by phone. 

13. Charlize Theron for Raymond Weil Watches

Year: 2005
Outcome: Settlement For Undisclosed Amount

In 2005, Charlize Theron signed a massive deal with watch brand Raymond Weil, agreeing to appear in ad campaigns and exclusively wear their watches publicly. Later, Theron also signed to represent the fashion house Dior, making an expensive mistake in the process. 

Charlize Theron for Raymond Weil Watches ©Denis Makarenko / Shutterstock.com Charlize Theron for Raymond Weil Watches ©Denis Makarenko / Shutterstock.com

Theron wore a Dior watch to a movie premiere and was promptly photographed wearing it. The word got back to Raymond Weil, who sued her on the grounds of breaching her contract with the company. She admitted her error and settled out of court for an undisclosed amount of money, but certainly enough to prevent her from making the same mistake again. 

14. Cristiano Ronaldo for Facial Fitness Pao

Year: 2014
Outcome: Mocked On The Internet

Cristiano Ronaldo seemed to know he would become a laughing stock when he did a commercial for the Facial Fitness Pao, a Japanese device that promises a slimmer face by exercising the facial muscles. Not only did he not actually use the device, but the look on his face makes him appear mortified to have been roped into such an ad. 

Cristiano Ronaldo for Facial Fitness Pao @r/funny / Reddit.com Cristiano Ronaldo for Facial Fitness Pao @r/funny / Reddit.com

The commercial starts with people demonstrating the goofy device, which is inserted in the mouth and when chewed on causes two arms on either side to flap around. When it gets to Ronaldo, he looks embarrassed and flaps the device with his hand. While he must’ve been paid a pretty large sum to appear in the commercial at all, one wonders if his pay was docked at all for refusing to participate 100%.