23 Hilarious Celebrity Photo Fails

Get Started

Oh wow, these are truly terrible.

23 celebrity photo fails that are all the cringe. Thanks to social media, we're used to celebrity photo fails. Heck, a lot of celebrities even post their fails on purpose. There was a time, though, when many of our favorite stars didn't have social media -- not because they hadn't signed up yet -- but because it didn't' exist. *GASP!*

In those days, you went to a photo shoot with a professional photographer and kind of just did what they told you. Sometimes it was hard to draw the line between high art and just a high photographer and things got... a little weird. That's where the magic happened. That's what these photo are. Magic.

How magic are they? How about Leo DiCaprio in mom jeans, laying on a pile of fruit, manhandling a bunch of bananas? Or how about Sandra Bullock topless in jeans made out of different colored denim patches, accessorized with hair flowers and weird sunglasses? Or Iron Mike Tyson lovingly cradling pigeons, or as they're referred to in most cities, rats with wings? I'm totally not making any of this up.

Come, take a ride through the world of bizarre celebrity photo shoots and extra weird candids from back when embarrassing pictures actually were embarrassing. Get Started
About Stars

Romances, breakups, weddings, fitness, fashion, and style...you name it, we've got the Hollywood highlights for you. Can't stay up-to-date on every breaking celeb news story? We also offer year's end roundups of celebrity chatter, red carpet fashion, blockbuster movie and TV trivia, previews of new releases, and more!