The 10 Most Awkward Celebrity Endorsements

Recently, the mama bear of the Kardashian clan, Kris Jenner, announced that she was having pleasurable intercourse with Bruce Jenner. OK, while she didn't directly say that, Jenner did state that the Zestra arousal lube she tried allowed her to continue having great sex, which is why she is now the face of the feminine sex aid! That's right. Now, you are likely to see Kris Jenner's face on a box of lube in the same aisle you frequent for other sexual needs.

But that's not the first time a celebrity stamp of approval made us feel uncomfortable about a product. Throughout the years, a number of celebrities have put their names on food brands, restaurant chains, and car rental companies that didn't make a lot of sense considering their image. Hit the jump to click through The 10 Most Awkward Celebrity Endorsements.

Written by Tara Aquino (@t_akino)

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When: 1973
It takes a guy who’s super secure about his heterosexuality to appear in pantyhose on a national television commercial that isn’t for RuPaul’s Drag Race. In the 1970s, New York Jets superstar QB Joe Namath was that guy. Yet, regardless of his reputation as the infallible ladies’ man of his time, finding out that the attractively smooth and slender legs that the camera slow-panned across in the commercial were actually his would discombobulate the manhood of even the toughest of males.

When: 1975
Before Simpson became infamous for double homicide, the star running back's commercials for Hertz were quickly making him known to even non-sports fans. Hertz ended its contract as soon as allegations of his domestic abuse sprang up. Unfortunately for the brand, it couldn’t escape its ties to jokes like “What drove O. J. to crime? A Hertz Rent-A-Car!”

When: 2006
To say that Ozzy Osbourne and I Can’t Believe It’s Not Butter were an unlikely pair would be an understatement. Not only have we never associated The Prince of Darkness with any food products, unless, of course, you count a dead bat, but we’re a bit confused as to why anyone would have the King of Mumbled Speech advertise a product that actually needs some explaining.

When: 2010
The West Coast rapper has given us a lot of life lessons. For instance, he taught us that when the pimp’s in the crib, someone better drop it like it’s hot. A lesser known yet equally importantly truth he enlightened us with is that “hack is wack.” Snoop teamed up with Norton Anti-Virus, the company that always pops up on your parents’ PC reminding them to renew their subscription, instilling in us that the one thing we shouldn’t be down with is cybercrime.

When: 1997
While having yet another discussion about Gorbachev at a dinner party, you can exhaust your audience on how he was the last head of the Soviet Union or banter about his views on freedom and democracy again. Or, you could refreshingly bring up how he is the reason you can have toppings from edge to edge on your pan pizza at Pizza Hut and actually mean it literally (not just as a another metaphor for communism).

When: 2011
In a nutshell (pun intended), Cameron and Tyler Winklevoss tried to intimidate Mark Zuckerberg by endorsing a product called Wonderful Pistachios. If the product’s name wasn’t menacing enough, the Winklevoss twins took a not-so-subtle jab at Mark Zuckerberg when they referenced someone potentially stealing their idea of cracking the pistachio in their hands in a commercial for the brand. As it still legally stands, Zuckerberg is worth a billion dollars and there is a commercial out there with one of the Winklevoss boys fondling nuts in his hand.

When: 2011
Rachel Bilson’s commercial for Magnum caused some confusion for everyone, not just sexually frustrated dudes. Let’s admit it: When we see a close-up of the beautiful Hart of Dixie star in a traffic jam approaching a man in a truck labeled “Magnum,” we think a certain condom company somehow signed a great celebrity spokesperson. It didn’t help clarify the situation when Bilson put the Magnum (the ice cream bar that was actually being advertised) in her mouth.

When: 2012
Kris Jenner is giving a whole new meaning to “keeping up with the Kardashians.” Mrs. Bruce Jenner, the 56-year-old mother to both an infamous sex tape star and a former radio show host who’d often give sex toy tips, decided to add her own two cents about the art of coitus. On her reason for endorsing the product, Jenner stated, “I tried Zestra. It really works, and it's so easy to use, so great sex is effortless.” No, this wasn’t another Kristen Wiig-powered SNL gag.

When: 2011
A rapper from Wu-Tang Clan with a new record coming out called The Crystal Meth probably shouldn’t be the one selling your kids candy. And yet, a music video about the sour-to-sweet gummies, in which Method Man also manages to reference a “dick pump,” can be found all over YouTube.

When: 1998
Viagra found possibly the best spokesman for its product in the history of commercials. After seeing the former presidential candidate, Bob Dole, try to talk to America about the problems of erectile dysfunction, men across the globe were so turned off that they ended up having to buy the drug. Well played, Viagra.