The 5 Saddest Second Careers of Celebrities

In the world of entertainment, versatility is a performer's lifeline, because no matter how much an audience may love it the first time they see it, they will only pay to see the same act for so long. For instance, Madonna sings, dances, writes and acts, and it's kept her in the spotlight for 30 years. Meanwhile, Jason Mewes plays Jason Mewes from time to time when Kevin Smith's Twinkie fund runs low. So that's why you'll see those occasional, bizarre crossovers with singers, actors, comedians and sports stars -- they're expanding their resumes so the world doesn't get bored with them and stop watching.

The following is what happens when a celebrity thinks, "Oh, I can do that," and because of their stature, nobody steps up to say, "Sit down, we need to have a talk. You're about to make yourself look catastrophically fucking stupid." God bless those people for retaining their silence. Otherwise, we'd have never been able to enjoy these cringe-inducing gems.

#5. Eddie Murphy's Repeated Attempts at Music


Very rarely, a big name star does something so disproportionately bad in comparison to their normal career that its echos can be heard for decades -- its shame tainting the laughter of our children's children's children. A perpetual shock wave of suck, defying the very core of physics, forever circling the globe and reminding us that, yes, this did indeed happen.

The first time that happened for Eddie Murphy was the well-known turdsplosion "Party All the Time." I'm not going to spend a lot of time deconstructing all the ways that this song and video were horrible because we've all seen it. Even children born after the '80s are shown this in school, as a warning. We've all felt the cold, clammy penis of death awkwardly slapping at our ear holes, and there's no need to rouse its anger again by reopening up the discussion. What's done is done. Lesson learned.

Wait, no it wasn't. No lesson was learned at all. Because there he is again in 1993, singing a song called "Whatzupwitu." And no, you're not hallucinating, that's Michael Jackson in the video. But ... how? Why? Wait, to hell with the "why" -- go back to "how" again, because ... how? The answer is found in a nine-minute-long video made the year before for Jackson's song "Remember the Time," which featured Eddie Murphy. That video was filmed and released in January of 1992, which is the exact time that Murphy recorded this volcanic lake of musical blasphemy. You don't need to be a historian to know it was a case of "Oh, hey, while you're here ..."

"But wait," you interrupt like a rude asshole. "If this time he had the King of Pop to help him write and produce the song, why wouldn't he take another shot at music? Maybe the first one was just a fluke bomb, so why not have another go at it?" Well, there are a couple of things wrong with that. First off, everyone always assumes that because "Party All the Time" was bad, it was a failure. It wasn't. That song peaked at No. 2 on the Billboard Hot 100, and No. 7 overall for the entire year.

That's his "suck it" look.

Second, Michael Jackson had nothing to do with the writing or producing of "Whatzupwitu." Eddie wrote and produced that himself. The actual advantage wasn't with that song -- it was with "Party," which was co-written and produced by Rick James. For you younger viewers, Rick James isn't a character played by Dave Chappelle. He's considered to be the greatest funk musician to ever live whose name isn't George Clinton.

The point is that the first time around, he had an idea for a song, he went to his friend Rick James and said, "I'd like to make this thing." Then they sat down and made it. Since they wrote it together, it had the heavy influence of a man who knew how to create and sell music that people would pay for. In Murphy's second attempt, he wrote a song in his spare time and used his opportunistic video filming with the world's most famous pop star to ask, "Can you sing background vocals for this thing I wrote?" And now he can never take it back.

"No, brighter. It's saturated enough when it burns the image onto their TV screens."

#4. Fall Out Boy's Bass Player Starts a Bar for Children


The entertainment world is full of celebrities opening their own businesses because in relative terms, fame doesn't last very long. You have to have something planned for your retirement after the public stops giving a shit about you; otherwise, you end up working as a security guard after being the most recognizable child actor in the world, like Gary Coleman, or evicted from your house after being the world's most famous heroin-shooting fucking embarrassment, like Courtney Love.

That's why you occasionally find yourself rolling your eyes as Bruce Willis tries to sell you his cologne or when you find out that Hulk Hogan had a failed restaurant called Pastamania.


Granted, the bassist from the band Fall Out Boy isn't exactly on the level of Hulkamania, or even a Hacksaw Jim Duggan for that matter, but that's actually why he decided to start his own bar. He was tired of not being let into elite clubs because the bouncers didn't recognize him. So in his own words, he started a bar "for all the rejects." No arguing with some asshole at the door. No palm greasing to get on a VIP list. Just show up, go in and get drunk with a hundred teenage girls and douchebags dressed in tiny pants with white belts. This is where you'll want to take notice of the very last line of that article I linked: "As for the fans, they'll probably need good fake IDs."

The person who wrote that must be a fucking prophet, because after numerous warnings by the police, the bar was finally shut down for repeatedly serving alcohol to minors. Which is kind of a blessing, I guess, since his original vision was "a place that anyone can go and have sex in the bathroom and not get in trouble." I'm assuming that if they let him talk long enough, he'd claim it was a place where you could bring your dogs and make a little extra money "if they know how to scrap." Or "fistfight a handcuffed minority without legal repercussions."

What I'm saying is that fucking in a public bathroom is illegal, you stupid emo cock.

#3. Ric Flair Finance, Baby! WOOO!


You can't say the name Ric Flair without someone in the room yelling out a high-pitched "WOOOO!" It's impossible. Try it the next time you're at a funeral.

The man has been in the wrestling business (fuck your "sports entertainment," it's goddamn "wrestling" -- "wrasslin'" if you're nasty) for 40 years. The guy is in better shape at age 63 than most of us will ever be at our physical peak. But even he knew that he couldn't do this forever. Even though he basically has. So a few years back, he set his sights on a non-physical retirement plan in the form of a finance and loan company. Not a bad idea, right? You invest as a partner, let the professionals handle the loans and just sit back and collect the money.

So he partnered with a few people who used his name and image to help propel the company into the spotlight. And they held nothing back. The logo featured him in the full sequined robe with his classic slicked back albino-white hair. They referred to their model as "The Figure 4 Process." They scattered ads all over the Net, featuring him in the flamboyant neon pink feather boa, doing the "WOOOOO" face. This was Ric Flair's company, and by God, he'd slap the lips off of your financial worries.

That's a screenshot from one of their old ads. Though I'd love to see the data of how many people actually clicked it.

That's a pretty solid plan if finance companies weren't some of the most difficult businesses to keep alive in a shitty economy. It sounds like the opposite should be true, doesn't it? The worse off the economy, the more people need to borrow money? But it turns out that when the shit hits the fan, people keep a tighter leash on their spending. And when they do take out a loan, the number of defaults goes through the roof -- partly because the interest rates and fees at those places are virtually criminal, and people find it impossible to keep up with the payments. This isn't speculation. My fiancee manages one of these places, and she deals with the data on a daily basis.

Ric found that out less than a year later, when the business imploded. Now, don't think this was just a case of him investing in a bad opportunity. This was something he had been planning with his wife for two years prior to diving in. He wasn't going in uneducated. The biggest problem with Ric Flair, though, is Ric Flair, and here's where the ultimate irony comes in.

That's the face of financial security right there, baby.

He's been in a near-homeless level of financial crisis for years. He's not only buried himself under multiple years of unpaid taxes, but he's defaulted on so many loans that he finds himself in a courtroom as often as the ring. He's been known to put up his title belts as collateral for loans on more than one occasion, and then skip the payments until he faces actual jail time. Want to know how bad it's gotten? Take a few minutes to read this. It's surreal.

On the upside, Ric did find a somewhat happy ending in the form of securing a commercial deal for an energy drink. See, as consumers, we're more comfortable with this. It's easier to trust in giving a few bucks for an energy shot that makes you scream "WOOOO" than putting your financial stability in the hands of a man who routinely whipped out his cock on passenger jets.

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