Top 10 Biggest Fails from the Most Successful People

Script written by Andrew Tejada

Top 10 Biggest Fails from the Most Successful People

These big names prove that you’re never too famous to mess up. Welcome to Watchmojo.com and today we’ll be counting down our picks for the Top 10 Biggest Fails from the Most Successful People.

For this list, we’re looking at the times where stars on the rise had big ideas that, at some point, crashed and burned in a very public way..

#10: Ja Rule’s Fyre Festival Fiasco

The 2017 Fyre Festival was a Ja Rule collaboration that few want to revisit. In 2017, the Murder Incorporated rapper partnered with Fyre Media to promote a “transformative” event on an island in the Bahamas. Guests were promised high quality food, villas to sleep in and performances from artists like Blink-182. It only cost event-goers anywhere between $1,000 to $12,000… to be severely disappointed. In place of fancy housing, they found hastily assembled relief tents. Instead of celebrity chef cuisine, there were cheese sandwiches and salad. And the headlining band canceled. Ja Rule apologized for the mess, offering refunds and promising a better experience next time.

#9: Seinfeld's Marriage Ref Bombs

Okay, hands up if you’ve heard of “The Marriage Ref”. If not, we don’t blame you. Comedian Jerry Seinfeld, known for his hilarious self-titled TV show, aimed to create and produce a unique game show. A married couple would appear on the program in the midst of a ridiculous argument. Then a panel of celebrities would give their opinions on the issue while the host, Tom Papa, would decide who was right. Despite an interesting premise, critical response ranged from lukewarm to extremely negative. Amid declining viewership numbers, “The Marriage Ref” took a permanent time-out after its second season. It seems the legendary comic simply couldn’t hit television gold twice.

#8: Eva Longoria Loses Two Businesses

Celebrities and businesses aren’t always a recipe for success… a lesson that Eva Longoria has unfortunately learned TWICE. The “Desperate Housewives” star opened her first establishment in 2008 with the Eve Nightclub and Beso restaurant in Las Vegas. Despite a positive reception for the food, the nightclub accrued millions in debt, eventually filing for bankruptcy in 2011. Longoria’s hunger for the culinary business lingered, leading her to open a steakhouse called “SHe” in 2012. However, after receiving a number of demerits from the health department, the eatery was forced to close its doors in 2014. Longoria has found success in other business pursuits, but restaurant luck has eluded her.

#7: Jada Pinkett Smith’s Metal Band

Jaden and his odd tweets might lead the Smith family in terms of strange behavior, but Jada isn’t without her own eccentricities. In 2002, the actress turned heads with her decision to start a metal band called Wicked Wisdom. Fans were skeptical, but she nonetheless rocked her way into Ozzfest by 2005. Some metalheads at the event weren’t receptive though, and Wicked Wisdom opened to boos and threats. Apart from social media posts, the public hasn’t heard much from the band since the release of their 2013 single. Jada’s acting seems to be keeping her busy these days, so it may be a while before we see her headbang again.

#6: M. Night Shyamalan's "The Last Airbender”

Shyamalan won audiences over with inspired critical darlings like “The Sixth Sense” and “Unbreakable”. Though his films were progressively less-well received after that, “The Last Airbender” was considered a colossal bomb. The film adapted the award-winning Nickelodeon show about a young boy gifted with incredible powers meant to bring balance to the world. The rough plot is about all Shyamalan got right. In his movie, the humor of the original show is practically nonexistent, the acting is awkward and the fast paced action is slowed to a crawl. Even the main character’s name is pronounced differently! With a 6% rating on rotten tomatoes, it’s a serious black mark on Shyamalan’s resume.

#5: Kim Basinger Buys Most of Braselton

Everyone’s made a purchase they’ll regret, like a snuggie or a gym membership. But a town? Back in 1989, actress Kim Basinger and investors put 20 million dollars together to acquire land and property in Braselton, Georgia. She had big plans for the small town of 500 people. Buildings would be revitalized! A recording studio would be built! There may even be a theme park! Unfortunately, none of it ever materialized. Around the time she filed for bankruptcy, Basinger sold Braselton for just over 4 million dollars. Basinger certainly succeeded in getting this town’s name out there, though not in the way she intended.

#4: Kanye's Pastelle Fashion Line

It’s hard to imagine Kanye West being quiet about a new venture. Yet, the mysterious nature of his Pastelle brand is what got people talking. Throughout the late 2000’s, Kanye hinted at a new clothing line by making random appearances with some of the pieces and even referencing the business in his hit song “Stronger.” After much anticipation, Pastelle was given a release date of October 2009. Before the first sale could be made, the line was canceled. Though it’s hard to tell if Pastelle would have generated the buzz that Kanye’s Yeezy line does, the level of excitement surrounding even the rumors of its return show that the brand still deserves a proper release.

#3: Vince McMahon's XFL League

What if we took the gameplay of the NFL, added the flair of the WWE and called it the XFL? What could go wrong? Well, WWE Chairman Vince McMahon can tell you. Taking place during NFL’s offseason, the XFL league was billed as a more entertaining version of football. Mics broadcast staff conversations throughout the game, players were allowed to choose nicknames for their jerseys and the coin toss for the ball turned into an all-out-scramble for possession. Although the league made things interesting, it was far from a hit with sports fans and ratings tanked. After one season, the XFL was over, fumbling millions of dollars of investment money on its way down.

#2: Michael Jordan’s Baseball Career

In 1994, NBA Superstar Michael Jordan announced he would be pursuing a career in baseball. While his motivations for making the switch can be debated, a fact that can’t be disputed is the fact that he simply wasn’t good enough. To be fair, he was an excellent baseball player, just not MLB material. Jordan initially tried out for the Chicago White Sox but after a shaky preseason performance, he was sent over to their minor league team, the Birmingham Barons. In his opening game, he went 0-3 while at bat. Jordan’s batting average remained low through the season as his error numbers rose. After a year with the Barons, he announced his return to basketball.

Before we stumble onto our top pick, here are some honorable mentions.


Natalie Portman's Vegan Shoe Line

Mariah Carey's "Glitter"

Katy Perry’s "Witness" Album

#1: Oprah Winfrey's OWN network

If anyone’s got a magic touch, it’s Oprah. Everything from her talk show to her book recommendations found great success. But as Oprah’s box office bomb “Beloved” proved, not everything she touches turned into instant gold. In the mid 2000s, the media queen unveiled a partnership with the Discovery Channel to launch the OWN TV network in 2009. However, behind-the-scenes issues lead to the networks’ debut to be delayed for 2 years. After OWN premiered in 2011, low ratings and staff layoffs had critics declaring the channel a bust. In true Oprah fashion, she made moves to turn the network around, but not before a sobering brush with failure.