It seemed to start out well enough, with a reported $1 million paycheck for her January spread in Playboy but it ended with reports of the 26-year-old starlet owing more than $200,000 to the IRS.
In March, a Los Angeles judge took the troubled actress off probation from her 2007 DUI case, praising her for doing "everything that this court has asked of her."
But just over a week ago her probation was revoked after she was charged with lying to police, driving recklessly, and obstructing an officer from doing his duties after she crashed her Porsche on the Pacific Coast Highway in June.
Since the crash, Lohan's problems have piled up. In September, she was arrested outside New York's Dream Downtown hotel when a pedestrian claimed she hit him with her car and did not stop. The Manhattan District Attorney's Office declined to prosecute that case.
That same month, Lohan was involved in a hotel-room quarrel that began over a set of cell phone photos of her allegedly taken by a part time Congressional aide, Christian LaBella. Lohan claimed LaBella had assaulted her, which led to his arrest, but the misdemeanor charges against him were later dropped.
In October, police were called to her Lohan's home on Long Island after a report of a fight between her and her mother. An investigation revealed "no criminality."
And in November, she was arrested after a New York City bar brawl in which she allegedly punched a Palm Beach psychic. She faces a misdemeanor assault charge in that case.
Fortunately for her, Lohan has had no shortage of offers for help. In fact, three of Hollywood's biggest stars have reached out to her. They have come bearing gifts and advice for the troubled starlet. In honor of the season, we take a look at Lindsay's three wise men.