Celebrities have been used for advertisements since Ancient Egypt had Cleopatra market a Cairo-based cat food brand. Since then, famous figures throughout time have been tied to brands, such as Martin Luther to the, at the time, popular 95 Reese’s ad campaign. (Just kidding.)

In this day and age, celebrity endorsements run rampant throughout all facets of media. Some of these turn out to be embarrassing for both the celebrities involved and the brand being endorsed. Here are some of the most embarrassing A-List celebrity advertisements.

  Brad Pitt and Toyota (Japan)

This Toyota commercial was designed, produced and directed by a 13-year-old Japanese girl. There could be no other explanation for why Brad Pitt and a Ricky Martin song were inexplicably brought together to advertise an awful car company. (Insert Prius joke here.)

  Woody Harrelson and Miller Lite

Despite Miller Lite paying Woody Harrelson to star in a commercial, they paid some random narrator to do the voiceover for it and it’s worked into the commercial as though the narrator phoned it in last minute. It’s already embarrassing enough to try to convince someone to drink a beer that college freshmen would pass over for Keystone, but the storyline in this commercial is awful. It ties a bicycle race in New York City to a race to get free Miller Lite. A trucker convoy would be more accurate, or a race of morbidly obese hicks on motor scooters.

  Mel Gibson and PSA

Terrible acting or drug-induced? Thank Mel Gibson for this commercial. If it weren’t for its amazing success we would all be getting our mansions raided every time we reached for a daily vitamin supplement.

  Arnold Schwarzenegger  Alinamin V Energy Drink (Japan)

This commercial is one of the nightmares you have when you pass out after taking LSD in Japan while watching an Arnold Schwarzenegger movie.

  Jaleel White and Urkel-O’s Cereal

He’s Steve Urkel. He raps. He mentions his love interest from Family Matters, Laura, more than once. I’m embarrassed for even posting this on here.

  Tyler the Creator and Mountain Dew

Mountain Dew commissioned Tyler the Creator to develop a commercial for them. It never made the air and is hard to find because it’s embarrassing for the brand. The commercial is filled with racial stereotypes and makes fun of domestic violence. I don’t know what Mountain Dew expected from Tyler the Creator – clearly no one from the brand ever listened to any of his music.