Screen siren Veronica Lake, who is famed for her femme fatale roles in 1940s movies including This Gun for Hire and The Blue Dahlia, not to mention her much-imitated wavy hairstyle, had a serious alcohol addiction that contributed to her decline as a star. Lake declared bankruptcy in 1951 at the end of her film career.

In 1894 the Father of American literature declared himself bankrupt in a New York state court. His debts amounted to $100,000, around $2.9 million when adjusted for inflation. Fortunately, Twain recovered financially, with the help of Gilded Age industrialist Henry Huttleston Rogers, and paid back his creditors in full despite being under no obligation to do so.

From tennis court to the UK's High Court, Boris Becker was once estimated to be worth over $131 million but was declared bankrupt in 2017 in London with debts believed to total $4.1 million owed to the private bank Arbuthnot Latham. According to the German press, the six-time Grand Slam champion may owe his many creditors as much as $70.7 million.

Becker's financial nightmare began in 2001 when he was ordered to pay a divorce settlement to ex-wife Barbara and paternity payments to model Angela Ermakova, which totaled $20 million. And it's all been pretty much downhill from there. In a bizarre twist to the saga, the tennis legend tried to claim diplomatic immunity from bankruptcy in 2018 based on his role as attaché for the Central African Republic, but later dropped the claim. In 2019, Becker was charged of hiding assets including a property in Chelsea, London and £1.2 million ($1.7m) in cash. Then in October 2020 Becker was charged for not disclosing his trophies and medals to bankruptcy trustees, as well as sending payments to individuals, although the former tennis star denied this. The trial is planned for September 2021, and if he loses he could face seven years in jail.

Fashion entrepreneur Karen Millen co-founded her eponymous company in 1981 with just £100 ($220) and opened her first store in Maidstone, England in 1983. The British chain expanded throughout the 1980s and 1990s and, by the early 2000s, Karen Millen boasted 130 stores across the world. In 2004, the business was acquired by Icelandic company Mosaic Fashions and Millen cashed in to the tune of £35 million ($65m).

Despite the windfall, Millen ended up in deep financial trouble. The former fashion boss claims she was defrauded by Kaupthing, the failed Icelandic bank that financed the acquisition of her company, and that she was roped into a sketchy tax avoidance scheme, both of which cost her dear. In 2016, Millen was declared bankrupt by the UK's Inland Revenue after failing to pay a £6 million ($7.8m) tax bill.

The second most-charted female artist of all time in the US after the late Aretha Franklin, Dionne Warwick scored 69 singles in the Billboard Hot 100 over her long career. In spite of her incredible chart success, the six-time Grammy Award-winning artist had no choice but to file for Chapter 7 bankruptcy in 2013, citing $10.7 million debts. That's the equivalent of $11.6 million today. 

Warwick claimed her finances were grossly mismanaged over a number of years, and that those in charge failed to settle bills of just under $7 million owed to the US tax authorities. The That's What Friends Are For singer is currently suing the Internal Revenue Service over the matter.

Actor Burt Reynolds died in 2018 and left the world with a respectable net worth of $5 milllion, but the Smokey and the Bandit and Boogie Nights star had plenty of financial headaches to deal with during his life, which nevertheless he resolved. After his costly divorce from Loni Anderson in 1993, Reynolds' finances took a turn for the worse.

Breaching a major Hollywood contract can lead to financial ruin as A-lister Kim Basinger discovered when she pulled out of the movie Boxing Helena. Ruling against Basinger, a court awarded Mainline Pictures $8.1 million. As a consequence, the star filed for Chapter 11 bankruptcy in 1993, citing debts of $11 million (£7.6m) and assets of up to $3 million. The breach of contract debacle was eventually settled for $3.8 million.

Superstar of the early 1990s and wearer of parachute pants, MC Hammer, aka Stanley Kirk Burrell, was earning $33 million a year at the height of his fame. The U Can't Touch This singer may have been pulling in serious cash, but he was spending it like water. As well as dropping $500,000 a month for a staff of 200, Hammer snagged a sprawling estate and installed gold-plated gates, a recording studio, swimming pools and a movie theater.

The judgments against the rapper ranged from a $6 million award to rapper Rick Ross's former girlfriend Lastonia Leviston for posting an intimate tape of her online without her consent, to $17.2 million issued to a business partner who accused 50 Cent of stealing the design of his Sleek by 50 headphones. He has since cleared his debts, helped by a payout of $13.65 million from lawyers after he won a legal malpractice lawsuit.

Nelson was eventually stung for $16.9 million by the service and released the album The IRS Tapes: Who'll Buy My Memories in 1992 to help pay off the debt. In 1993, Nelson settled for a bargain $9 million, and today the country music veteran is worth a very respectable $15 million.

Un-break My Heart singer Toni Braxton was left broke in the mid 1990s after her record company awarded her a pathetic $2,000 in royalties despite the artist selling 40 million records. Though her overspending wasn't as extravagant as the media claimed at the time, it didn't help and she filed for Chapter 7 bankruptcy in 1998 owing a total of $3.9 million.

Braxton had to sell her Grammys and American Music Awards to help make ends meet and endured a humiliating interview with Oprah Winfrey, who castigated her for mismanaging her finances. The singer declared bankruptcy again in 2010 with debts of $18.3 million against assets of up to $1.6 million, this time due to medical problems. Sadly her money woes haven't stopped there, and in 2019 it was revealed that Braxton owed $340,252.99 in back taxes to the IRS and $116,154.64 to the State of California Franchise Tax Board for 2017.

Hunt, who was once considered the planet's richest person, lost out big time when the price of the commodity plummeted on so-called Silver Thursday in 1980. He went on to file for bankruptcy in 1986 with $500 million in debts and $100 million in assets, and even had to sell off a $20 teapot at one point.

The country's most disreputable banker, Einarsson was sentenced to five years imprisonment in 2013 (later reduced to four years) for manipulating the markets, and was declared bankrupt in 2015 with debts of $2.1 billion.

In what became Australia's most infamous individual insolvency case, controversial businessman Alan Bond, who had significant interests in sport, media and mining, filed for bankruptcy in 1992, after failing to settle a personal guarantee on a loan for a mining venture totalling $137.3 million.

Ireland's one-time richest person, Seán Quinn had a personal fortune of $6 billion in 2008, according to Forbes. The rags-to-riches tycoon started out with a humble gravel business which he grew into a colossal conglomerate spanning construction, manufacturing, real estate, insurance, and more. 

The tycoon had invested heavily in the Anglo Irish Bank using risky financial instruments and lost bewildering sums of money when its share price collapsed following the 2008 crash. Quinn's liabilities totaled $3.2 billion and the magnate was declared bankrupt in 2011 in Northern Ireland and in 2012 in the Republic. Compounding his fail from grace, Quinn went on to serve nine weeks in prison for asset-stripping and non-cooperation with the banking authorities.

Now read: Billionaires behind bars