She was once one of the world's highest-paid actresses, earning £5million (NZ$8m) a movie.
But a decade on, Lindsay Lohan is facing bankruptcy after failing to pay rent on her £3.5million London flat.
Lawyers for the landlord of the property, which is in the exclusive Knightsbridge area, have issued the 30-year-old American star with papers demanding payment of £77,600, and will petition at court for her bankruptcy on November 8 if she fails to pay up.
Solicitors Child & Child hand-delivered a letter to Miss Lohan seeking the unpaid rent for the six months to August.
In a further blow, Miss Lohan's ex-fiancé, Russian property tycoon Egor Tarabasov, 23, claims she took up to £24,000 worth of his belongings - including a Rolex Oyster watch, designer clothing and a small gold crucifix. A friend said he has now spoken to police, demanding her arrest for theft.
The Mean Girls actress's financial woes are the latest in a string of personal crises marking the reversal in her fortunes. She has had numerous stays in rehab for alcohol and drug problems, was convicted of drink-driving and shoplifting and has spent time in jail.
Most recently, she and Mr Tarabasov had several fierce rows, one of which saw police called to the flat, while footage emerged of them brawling on a Greek beach
Last night the friend of Mr Tarabasov said: 'Lindsay is in an absolute mess. She has blown virtually all her money, and has basically resigned herself to being declared bankrupt... The whole situation is incredibly tragic, and for Lindsay this is an astonishing fall from grace.'
Mr Tarabasov sent an inventory to his lawyers of the items he claims went missing from his flat, which featured some extraordinary pieces including a Luc Waring painting, a print of Tracey Emin's The Kiss, a diamond-studded ring worth £1,300 and a £5,500 Panerai Luminor Marina watch.
It also included a pink floral Chanel bag, which he said he bought for her as a gift but she had never used.
Mr Tarabasov's friend said the pair are 'at loggerheads' over the items, adding: 'The thing he really wants back and which, ironically, is of very little monetary value, is a small gold Russian orthodox cross which was given to him by his dead godfather.'
Miss Lohan and Mr Tarabasov were introduced at a party through mutual friends last October and moved into the flat in March this year.
The 12-month tenancy agreement, which had a six-month break clause, was in the actress's name, but it is understood Mr Tarabasov paid a three-month deposit upfront in full.
The couple, who got engaged in April, agreed to split the £3,000-a-week rent, but Mr Tarabasov claims Miss Lohan never paid her share.
Their relationship ended in July following the row at the flat when police were called.
It is believed Miss Lohan is still the legal tenant, and stayed at the property for a few days last month after returning to London to film for Jamie Oliver's new cookery show.
Miss Lohan started her career when she was just three as a model for Vogue, before landing her big break at the age of 11 in the film The Parent Trap. She starred in movies including Mean Girls, Freaky Friday and Just My Luck, which grossed a combined fortune of around £410 million. She also enjoyed advertising deals and a record deal.
But as her career began to stall, her behaviour became more erratic. There were numerous of her wild spending habits, including claims she spent £300,000 in a year at the infamous Los Angeles hotel Chateau Marmont.
This is not the first time she has apparently been unable to pay her rent. In 2012 friends claimed she could not meet the £5,000 rent for her Beverly Hills mansion, and was asking to 'borrow' money.
Last night a spokesman for Miss Lohan declined to comment.