Last week, Tanning Vegas filed a lawsuit against Lohan claiming that she owes the company more than $41,000 in unpaid tanning fees she racked up between 2007 and 2009. In 2009, the same company accused Lohan of stealing its formula for a spray tanning product she sold under her Sevin Nyne label.
In December, Lohan came under investigation for allegedly assaulting a staffer at the Betty Ford Clinic, where she carried out her most recent round of rehab.
Lohan lost her most high-profile job of late in November. She was slated to star in the biopic of porn star Linda Lovelace, but because of her recent troubles, the film's director switched her out for "Watchmen" actress Malin Akerman.
Lohan butted heads with E-Trade in 2010. She sued the financial services company for $100 million for a talking baby commercial that, according to her, made a mockery of her personality. The two settled in September for an undisclosed amount.
2010 wasn't exactly a banner year for Lohan: In September, she tested positive for drugs and had her second prison stint before beginning rehab at Betty Ford. She also spent part of the summer in a separate rehab program.
The real lowlight of Lohan's year probably was the 14 days she spent in prison. In July, she received a 90 day sentence for violating her 2007 probation.
This was after she missed a May probation hearing because, according to her, someone stole her passport while she was at the Cannes Film Festival. Lohan was spotted partying in France prior to coming back to Los Angeles, where a warrant was issued for her arrest. She escaped jail time but was ordered to attend weekly alcohol education classes and wear an alcohol monitoring bracelet.
It all pales in comparison to Lohan's biggest blunders yet, a set of screw ups that continue to make her life a mess. In 2007, she was arrested for two DUIs, one of which ended with police finding cocaine in her pocket. That year's infractions led to 84 minutes of jail time, multiple stints in rehab and a probation sentence with which Lohan still grapples nearly four years later.
ABC News' Scott Shulman contributed to this report.