The 10 Most Embarrassing Celebrity Side Projects

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Celebrities are always coming up with side projects and trying to explore new creative genres. It’s certainly not a new phenomenon — think the Rat Pack — although we do think in the modern era there’s probably some building pressure to “expand the brand” across industries. However, some celebs, though often beloved in one area, can branch out a little to quickly or a little too far, and well, embarrass themselves. Hey, it happens to the best of us (obviously, because James Franco is on this list), but that doesn’t mean we can’t judge. Click through for our roundup of the most embarrassing celebrity side projects — and let us know if you have any famous fails to add to the list.

Leighton Meester’s Music Career

We were basically fine with Meester’s musical attempts, although never particularly enthused by the results, until this song hit the internets. We know the rumor is that it’s an old song only recently seeing the light of day, but that maybe doesn’t matter that much. Two years ago she was still Blair. And also a human with ears.

Joaquin Phoenix’s (Pretend) Rap Career

Remember when Joaquin Phoenix decided to quit acting and become a rapper? And then he seemed like a crazy person on Letterman? And then we found out that it was all a joke to somehow support a mockumentary he was making with Casey Affleck and that we were actually supposed to know this the whole time, because it would be ludicrous for a 35-year-old to retire from acting. Ultimately, the film was a flop, and since no one actually saw it, the whole debacle ended up seeming like a complicated joke with no punchline.

Britney Spears’ NYC Restaurant

Running a restaurant is a complicated business. Not to say that Britney isn’t capable of complication — especially in 2002, pre-breakdown, and at a time when she could still be embarrassed by stuff like this — but she apparently wasn’t cut out for the food industry. Britney abandoned NYLA, which was supposed to be her “hip, hot, sexy New York lounge,” after numerous health code violations, leaving $400,000 in unpaid bills. As if all those adjectives weren’t embarrassing enough.

James Franco’s Class on James Franco

We know, we know, James Franco’s college class on himself is more performance art. And we love James Franco, we do. We think his millions of projects are adorable. And cool. And we know he’s way awesomer than us. But, come on. Master Class: Editing James Franco… with James Franco? This is a “Master Class”? This is a class? Ay. There’s such a thing as overkill, guy.

Pete Wentz’s Bar

Angels & Kings, Wentz’s East Village bar got slapped with a closure order for serving alcohol to minors. Ah, Pete Wentz, polluting the minds and bodies of helpless children. Just like your work with Fall Out Boy. Zing!

Jada Pinkett Smith’s Nu-Metal Band

Maybe it’s just us, but — what? We don’t even know if this is good nu-metal or bad nu-metal, but it hurts our ears. Is this just a rebellion against Big Willie Style? Or is Jada secretly the keeper of the dungeon in the Smith family castle? Either way… awkward.

Michael Jordan’s Baseball Career

Honestly, his actual stats aren’t that embarrassing for the minor leagues. But for someone who was the epitome of physical ability for a generation of sports fans, the fact that he even kind of sucked at baseball was pretty demoralizing. Add to that all the fake retirements and the fact that he’s now into golf, and you’ve got yourself some major embarrassment.

Sylvester Stallone’s Oil Paintings

Rocky’s scribbled, expressionistic paintings, which he exhibited for the first time at Art Basel in Miami Beach in 2009, have sold for up to $50,000 dollars. Well, they’re not the worst things we’ve ever seen, but they’re nothing to write home about, and they certainly wouldn’t have been given much fanfare had they not been doodled by the man himself. Keep giving them to your family members as Christmas presents, Stallone, and make us another movie.

50 Cent’s Performance-Enhancing Condoms

Rapper 50 Cent, who had planned to build a super-condom with chemicals to boost male performance, abandoned the project late in 2009. He said, “It just didn’t work out because I wanted things in it that wouldn’t work. I wanted things that would prolong sexual performance. You could just put it on and go.” We want to know: Fiddy, what things did you want in it that they couldn’t put in it? Do you have something to tell us? Does Chelsea know what we mean?

The KISS Kasket

Okay, so this is really more a case of a celebrity merchandising attempt gone horribly wrong than a true side project — Gene Simmons isn’t about to become a custom casket maker or anything — but we just had to include it. A KISS casket that doubles as a “Giant Kiss Cooler”? It’s the ultimate in tasteless. When introducing the product, Gene Simmons reportedly quipped, “I love livin’, but this makes the alternative look pretty damn good.” No, no it does not, Gene Simmons. For shame.