If an endorsement deal's successful, it can earn a star staying power, a free supply of the product in question and, ideally, a big ol' paycheck. If it's not so successful? Well, then your head's just plastered on a condom.

Over the years, actors, singers and socialites have famously applied their names to products—and well! Britney Spears and Pepsi were a match made in heaven, Nicole Kidman proved to be a perfect fit for Chanel and you'd be hard-pressed to step into an H&M without spotting David Beckham's likeness drawn onto a sales rack. Still, for every job well done, there was a job certain celebs probably wished had gone undone.

When Bella Thorne's mug famously (and strangely) appeared on boxes of Cocoa Puffs earlier this year, we were inspired to dig through the archives of the most abstract, unexpected and downright weird cases of high-profile endorsement deals. And what we unearthed was truly fascinating—Mary-Kate and Ashley Olsen's faces on Aquafresh canisters and Rihanna taking a swig from longneck beers were just the beginning—when we finally got to Justin Bieber's nail polish, we knew we'd struck gold.

Above, you'll find what we're confident is a nearly complete collection of the the most perplexing sponsorship Hollywood has offered. Take a look and see how many of you can manage to scroll through before you start to laugh your ass off!

Look back at celebs who were born with silver spoons in their mouths: