Chaka Khan flirted with success in the late '70s and early '80s, but it wasn't until she recorded one of Prince's songs (apparently he wrote every song in the 1980s) that she hit it big.
She came back from the brink of mediocrity, riding the wave of success that "I Feel For You" brought. But it was short-lived. She crashed back into obscurity a few months later.
In the late-1990s, firmly in her place performing at Indian casinos and state fairs, Chaka tried her hand at the her next logical career move -- she became a chocolatier.
True, she wasn't in the test kitchen figuring out the next great way to put chocolate and peanut butter together, but she did lend her name to it -- and cashed the few checks that came in from the venture.
No. 2: The Kardashians' credit card
Ever wanted to live like a Kardashian? Yeah. Me neither.
But apparently there was a business concern out there that believed there were enough vapid people who would happily shell out money to have a Kardashian-branded credit card.
In 2010 the queens of spending thought it would be a great idea to endorse (and have their pictures emblazoned on) a prepaid credit card. Turns out only about 250 people agreed with them.
The card also brought with it a bevy of obscene fees, drawing the ire of Connecticut Attorney General Richard Blumenthal.
He said: "I am deeply disturbed by this card's high fees combined with its appeal to financially unsophisticated young adults."
The only winner was Blumenthal, who managed to slam both the Kardashians and the 250 dimwits who got a card in the first place.
In the end, the Kardashians sued the credit card company in an effort to distance themselves from this horrid idea.
No. 1: Hulk Hogan's Pastamania!
In 1995, Hulk Hogan (real name Terry Bollea) foresaw an age where former wrestlers could offer more to the world than ripping off their shirts and making crazy eyes at TV cameras. A few years later Jesse Ventura would take on the world of politics, but before that, Hogan tried to change humanity via pasta.
After leaving the world of wrestling, Hogan opened a restaurant inside the Mall of America called Pastamania! It featured such palate-ticklers as Hulk-U's and Hulkaroo's.
Unfortunately, there wasn't enough belief in Hulk's vision (Philistines!), so Pastamania! closed its doors within just a year of opening.
It's too bad all this transpired almost 20 years ago. Given his penchant for reality television, he could have asked Gordon Ramsey to help him out and he would have been on another show.