17 celebrities who lost big money to bad investments

Famous peoples' investment fails

While some celebs have managed to supplement their fortunes with savvy investments, not every star has the Midas touch.

From Bono to the high-profile victims of Bernie Madoff's infamous Ponzi scheme, read on to discover some of the biggest celebrity investment fails of all time.

All dollar values in US dollars.

Mark Twain: the Paige Compositor

Proving that poor financial management is nothing new, the writer Mark Twain lost a fortune when he invested his life savings into the Paige Compositor. The doomed device was a mechanical typesetting machine invented by James Paige in the late 1800s and was so complex that it reportedly had 18,000 parts.

Sources claim that Twain invested $300,000 (over $10.5 million in today's money) into the development of the machine. Unfortunately, fewer than half a dozen machines were ever made and James Paige soon went bankrupt, taking Twain down with him.

Kim Basinger: Braselton, Georgia

In 1988, L.A. Confidential star Kim Basinger made a slightly more unusual investment. Instead of buying into a company or product, Basinger decided to spend $20 million on buying the majority of land in Braselton, a town in Georgia. Her investment would be the equivalent of a whopping $56 million in 2026 money. Unfortunately, the purchase didn't pay off.

The actor had intended to turn the town into a movie-themed tourist attraction. However, facing personal bankruptcy, she ended up selling the land just five years later for a comparatively measly $1 million, the equivalent of $2.3 million today.

Jay-Z: J Hotels, Fela!

Rapper Jay-Z may be a billionaire today, but not all his investments have gone to plan. The year 2007, in particular, is one the musician may want to forget due to a series of failed money-making schemes.

These included a $50 million investment ($80m in today's money) in a real estate project called J Hotels, to be built in New York's Chelsea district. The looming real estate crash soon put paid to the project's aspirations, and Jay-Z became locked in an expensive legal battle after suing his lenders, according to AfroTech.

That same year, he also lost money on the Broadway show Fela!

Torii Hunter: inflatable furniture rafts

Former professional baseball player Torii Hunter might have excelled on the field, but his investment strategy certainly missed the mark. In the early 2000s, Hunter reportedly invested $70,000 – the equivalent of around $130,000 in today's money – in a company that supposedly made inflatable rafts designed to sit under items of furniture.

The idea was that if your house started to flood, you could inflate the rafts and your furniture would stay safe and dry. Ironically, the money Hunter 'sank' into the project was never seen again. 

Selena Gomez: Postcard on the Run

Unlike her ex-boyfriend Justin Bieber, who lucked out by investing in Spotify in its formative years, Selena Gomez hasn't been as fortunate as a venture capitalist. In 2011, Gomez invested $750,000 in the postcard-creation app Postcard on the Run, which was also featured on ABC's Shark Tank show.

Her investment would be worth over $1.1 million in today's money – but the app failed to take off and was shut down in October 2015. 

However, it hasn't put Gomez off. She's since become both owner and investor of the renowned New York ice cream brand Serendipity, which has been operating since 1954. 

Justin Timberlake: Stipple and MySpace

Justin Timberlake might be a talented actor and singer, but his investing success has been more mixed. In 2010, Timberlake invested in the image-tagging app Stipple. Four years later, the company folded.

Even worse, the entertainer was part of a consortium that bought the failing MySpace for $35 million in 2011, the equivalent of over $50 million today. This turned out to be a big mistake, and Timberlake reportedly sold his stake for just $1 to a fan in 2015.

He's since invested more successfully in businesses including audio company AfterMaster (of which he became co-owner) and fruit drink company Bai, which was acquired by Dr. Pepper Snapple for $1.7 billion in 2016, the equivalent of $2.3 billion today.

Michael Vick: dog fighting

"Michael is gullible, and he can be stupid." That's according to financial planner Michael Smith, who worked with NFL star Michael Vick for two years. Vick's successful sporting career came crashing down when he was convicted of financing a dog-fighting operation known as Bad Newz Kennels in 2007.

This sparked an onslaught of legal claims against him, with various banks and creditors accusing him of defaulting on loans he took out to finance other bad investments. Vick filed for bankruptcy in 2008 and has since said he was led astray by his financial advisors.

Arnold Schwarzenegger: Planet Hollywood

During the late 1970s, before his acting career took off, Arnold Schwarzenegger turned $100,000 into $1 million by investing in real estate. But his good investing work was almost undone in 1991 when he pumped cash into the Planet Hollywood restaurant chain, alongside Sylvester Stallone, Demi Moore, and Bruce Willis.

However, not even this A-list backing could save the chain from filing for Chapter 11 bankruptcy in 1999. Arnie officially cut his ties with Planet Hollywood in January 2000.

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Jack Nicholson: Tod Michael Volpe's art investments

Actor Jack Nicholson is one of many Hollywood stars who placed their money in the wrong hands. Tod Michael Volpe was a Manhattan-based art dealer who made a fortune by helping the rich and famous build their art collections.

But when Nicholson initially injected $600,000 into Volpe's art fund, the equivalent of $1.3 million today, he didn't know that Volpe never intended to invest it properly. Instead, Volpe sold a number of paintings and even an Aston Martin he co-owned with Nicholson without telling him, pocketing the profits for himself.

In 1997, Volpe was eventually arrested for defrauding his clients out of $2.5 million ($5.1m in 2026 money). He received a 28-month prison sentence.

Kevin Bacon and Kyra Sedgwick: Bernie Madoff's Ponzi scheme

When a deal seems too good to be true, it probably is. So it proved for actors Kevin Bacon and Kyra Sedgwick. 

During the 2000s, the Hollywood couple invested heavily in Bernie Madoff's notorious $65 billion ($99bn in today's money) Ponzi scheme and were among the worst-affected victims, losing tens of millions of their life savings.

John Malkovich: Bernie Madoff's Ponzi scheme

Like Bacon and Sedgwick, actor John Malkovich also fell victim to Madoff's Ponzi scheme in the 2000s. The Dangerous Liaisons star lost over $2 million in the scam, the equivalent of around $3.8 million today.

But he apparently took the loss in his stride, telling Details magazine: "I think it kind of reconnected me to how most people live all the time. And, unlike a lot of people that were involved in the Madoff thing, I could just go back to work, and it was fine. For me, in all honesty, it was a good life lesson."

Zsa Zsa Gabor: Bernie Madoff's Ponzi scheme

Hungarian-American actor and socialite Zsa Zsa Gabor also fell foul of Bernie Madoff's Ponzi scheme, along with her husband Frédéric Prinz von Anhalt. HuffPost reported in 2009 that Gabor lost $4.5 million in the scam, though other sources claim she lost as much as $10 million, the equivalent of $19 million today.

Gabor still had an impressive net worth, however, and was estimated to have a fortune of $40 million when she died aged 99 in 2016.

Elie Wiesel: Bernie Madoff's Ponzi scheme

It's bad enough when people are scammed out of their personal savings. But Holocaust survivor and Nobel Peace Prize winner Elie Wiesel lost everything when he fell victim to Bernie Madoff's Ponzi scheme, including his life savings and a further $15.2 million ($29m today) from the Elie Wiesel Foundation for Humanity.

Speaking to a panel hosted by Condé Nast Portfolio in 2009, Wiesel said: "All of a sudden, everything we have done in 40 years – literally, my books, my lectures, my university salary – everything was gone."

Steven Spielberg: Bernie Madoff's Ponzi scheme

Like Wiesel, Hollywood film director Steven Spielberg was also defrauded out of his foundation's funds by Bernie Madoff. Spielberg founded  The Wunderkinder Foundation in the early 1980s and Madoff was managing around 60% of the charity's dividend and interest income by 2006.

In total, the foundation lost around $340,000, around $650,000 today, while Spielberg himself also lost a chunk of his personal savings.

Kiefer Sutherland: Michael Wayne Carr's cattle scam

Yet another Ponzi scheme victim, 24 star Kiefer Sutherland lost an $869,000 investment in a cattle scam during the late 2000s, the equivalent of around $1.3 million today. Fraudster Michael Wayne Carr promised bumper returns by buying cheap cattle in Mexico and selling them to American farmers for inflated prices.

Carr was jailed for the fraud in 2011.

Bono: Palm

Through his private equity company Elevation Partners, U2 frontman Bono invested a massive $460 million – the equivalent of $705 million in 2026 – in the smartphone maker Palm between 2007 and 2008. The brand failed to hold its own amid the smartphone explosion monopolized by the likes of Apple and Samsung, contributing to Bono being labeled the worst investor in America by the financial blog 24/7 Wall Street. 

Although Bono had better luck with other investments, he also made a series of losses and Elevation Partners closed for good in 2015. 

Mark Brunell: Whataburger and real estate

Another sports star who invested poorly, retired NFL player Mark Brunell lost his entire $50 million fortune and filed for bankruptcy in June 2011. The football ace had invested in nine different enterprises, five of which went under. Brunell's doomed real estate firm Champion LLC suffered the heaviest losses, losing him $11 million in total, or the equivalent of $17 million in today's money.

According to the Daily Mail, he also lost "every penny" of his $9 million ($14m today) investment in the fast food chain Whataburger. 

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