Donald Trump 
Billionaire and proud owner of the least convincing rug in town, Mr Trump (he's always sounded like an ill-mannered Mr Man to me) has diced with bankruptcy a couple of times now. A decade ago he was on the brink of going spectacularly bust. His personal liabilities were around $900 million. His three casinos and Plaza Hotel were forced into bankruptcy, he lost his yacht and the Trump Shuttle (the mind boggles!), and Ivana snagged the mansion and $14 million in the divorce. In 2004 he again got into financial hot water when he had to declare his Trump hotel and casino resorts bankrupt. Donald's not too bothered by the jibes such as "If we still had debtors' prisons, Trump would be in the dungeon" and "Donald Trump is a third world nation" that were directed at him during his periods of insolvency. Bouncing back faster than a power ball, Mr Trump retaliated by saying "It doesn't matter - it's modern day thing, a legal mechanism" and even suggested that corporate bankruptcy offers "a ticket to expansion and competitive advantage." He might have bad hair and look like his face has been fashioned from a ball of dough but The Trumpster sure is resilient!
Darren Day
The former musical theatre star and You Bet! Presenter was declared bankrupt in October 2006 after blowing millions of pounds on a destructive celebrity excess lifestyle. Day, 38, earned in excess of £1 million a year when he was at his peak. However, he was recently forced to swap his £800,000 Hertfordshire home for a small rented semi in Brierly, Yorksire.
Gary Coleman
Arnold is bankrupt? What you talkin' bout Willis? Tis true. Little Arnold from the 1978-86 sitcom Different Strokes has had a spot of bad luck in the last few years. It's estimated that he earned $18 million from the show, but says his parents and former manager squandered the money. In an attempt to raise money in 1999, he sold some of his personal items in an online auction (haven't we all), including his size 4 ½ bowling shoes and some Afro picks. On Aug. 18, 1999, he filed for bankruptcy.
Eddie 'The Eagle' Edwards
1991 Great Britain's first Olympic ski jumper
Burt Reynolds
This old favourite filed for bankruptcy in the US in 1996. A couple of years earlier he had commented: "Like every American I’m having a cash flow problem right now. That’s why I’m an actor, not an accountant." More recently Reynolds appeared in UK TV ads for optician Dollond & Aitchison... Should have gone to Specsavers.
Kim Basinger
The L.A.Confidential actress earned so much money from her earlier films that she was able to purchase a town, Braselton in Georgia. Unfortunately she was then sued for breach of contract for pulling out of the movie, Boxing Helena, apparently after having not realised that the film was about a woman who's kept in box after having her limbs amputated... try reading the script next time, Kim! She was not able to pay the damages resulting from the suit and filed for bankruptcy in 1993 and had to sell the town she'd bought. As if things couldn't get worse she also married Alec Baldwin (the fat one of the Baldwin brothers), who famously got into trouble recently for calling his eleven year-old daughter a "thoughtless pig". What a charmer. Happily Ms Basinger's finances are in the black again these days.
MC Hammer
musician and entertainer, filed for Chapter 11 bankruptcy in 1996 because he did not have the income to support his lavish lifestyle and defend all the lawsuits that were filed against him. Now an ordained minister, MC presided over the marriage of movie star Corey Feldman.
Clarissa Dickson Wright
Clarissa Dickson Wright, of “Two Fat Ladies” TV cookery show fame, has been declared bankrupt on three separate occasions – 1975, 1982 and 2003. She has said that the first time was due to the champagne bill at her mother’s funeral.
Chris Eubank
Former world champion boxer Chris Eubank was declared bankrupt in November 2005, owing £1.3 million in unpaid tax to HM Revenue & Customs. He was forced to sell both of his homes in Hove, East Sussex, including his £4 million mansion.
Other Celebrities Bitten by the Bankruptcy Bug are:
Bez (Happy Mondays and Celebrity Big Brother Winner)
Jean-Christophe Novelli
Peter Jones
Francis Ford Coppola
Richard Harris
Marvin Gaye
Lynne Redgrave
Michael Barrymore
Henry Kelly (Host of 'Going for Gold')
Dustin Diamond (a.k.a. Screech from Saved By the Bell)
Anna Nicole Smith
Olivia Newton-John
Lisa 'Left Eye' Lopez (TLC)
Toni Braxton
George Best
Lynne Spears (Britney's Mum)
Walt Disney
Chaka Kahn
Keith Floyd
Tia Carrere (Wayne's World)
Corey Haim (Star of 'Lost Boys')
Cyndi Lauper
Gary Glitter
Zsa Zsa Gabor
Bill Roache (Ken Barlow in Coronation Street)
Rod Hull
Jim Davidson
LaToya Jackson
Adam Faith
Meat Loaf
Don Johnson
Mike Tyson
Richard Blackwood (ex-MTV Presenter)
Larry King (American Talk-Show Host)
Mickey Rooney
Jerry Lee Lewis
Tammy Wynette
Jeffrey Archer
Neil Hamilton