Lohan's debut studio album, Speak (2004), was certified platinum. Her second album, A Little More Personal (Raw) (2005), was certified gold. Earlier in 2005, Lohan starred in Disney's Herbie: Fully Loaded, another box office success. In 2006, she received positive comments on her work in independent films, including Robert Altman's A Prairie Home Companion and Emilio Estevez's Bobby. In 2007, two driving under the influence incidents led to Lohan being put on probation, and together with three visits to rehabilitation facilities caused the loss of several movie deals.
In 2008 and 2009, Lohan worked as a fashion model and launched the clothing line 6126. She resumed her acting career with recurring appearances in the TV series Ugly Betty in 2008 and starred in the TV film Labor Pains in 2009. She was featured in Robert Rodriguez's feature film Machete (2010). Between 2010 and 2103 Lohan went into rehabilitation three times, and spent much of her time entangled in legal problems stemming from misdemeanors and probation violations. In 2012 and 2013, she did further television work, including starring as Elizabeth Taylor in the biographical TV film Liz & Dick (2012). In 2013 she starred in Paul Schrader's independent film The Canyons.