Her career was interrupted in 2007 as two driving under the influence (DUI) incidents and three visits to rehabilitation facilities led to the loss of several movie deals. Resuming her career, she guest starred in the TV series Ugly Betty in 2008, starred in the 2009 comedy Labor Pains, and appeared in Robert Rodriguez's Machete in 2010. Lohan launched a second career in pop music in 2004 with the album Speak and followed up with A Little More Personal (Raw) in 2005. She has attracted significant publicity, particularly surrounding her personal life.
Lohan was born on July 2, 1986, in New York City and grew up in Merrick and Cold Spring Harbor on Long Island, New York. She is the eldest child of Donata "Dina" (née Sullivan) and Michael Lohan.Lindsay has three younger siblings, all of whom have been models or actors: Michael Jr. (who appeared with Lindsay in The Parent Trap), Aliana ("Ali"), and Dakota ("Cody"), the youngest Lohan child. Lohan is of Irish and Italian heritage and was raised as a Catholic. Her maternal family were "well known Irish Catholic stalwarts" and her great-grandfather, John L. Sullivan, was a co-founder of the Pro-life Party in Long Island. Lohan attended Cold Spring Harbor High School, where she did well in science and mathematics until grade 11 when she started homeschooling.
Lohan's parents have a turbulent history. They married in 1985, separated when she was three, and later reunited. They separated again in 2005 and finalized their divorce in 2007. Her father, Michael, is a former Wall Street trader and businessman who inherited his father's pasta business and has been in trouble with the law on several occasions,while her mother, Dina, is a former singer and dancer.
Lohan remained in the role for a year, before leaving to star in Disney's 1998 family comedy The Parent Trap, a remake of the 1961 movie. She played dual roles of estranged twins who try to reunite their long-divorced parents, played by Dennis Quaid and Natasha Richardson. The film earned $92 million worldwide, and critic Kenneth Turan called Lohan "the soul of this film as much as Hayley Mills was of the original", going on to say that "she is more adept than her predecessor at creating two distinct personalities". The film won Lohan a Young Artist Award for best performance in a feature film as well as a three-film contract with Disney.
At the age of 14, Lohan played Bette Midler's daughter in the pilot episode of the short-lived series, Bette, but resigned her role when the production moved from New York to Los Angeles.She also starred in two Disney television movies: Life-Size opposite Tyra Banks in 2000, and Get a Clue in 2002.
Lohan starred as Anna Coleman alongside Jamie Lee Curtis in the 2003 family comedy Freaky Friday. At Lohan's own initiative, her character was rewritten and changed from a Goth style to be more relatable. Critic Roger Ebert wrote that Lohan "has that Jodie Foster sort of seriousness and intent focus beneath her teenage persona". Freaky Friday earned Lohan the award for Breakthrough Performance at the 2004 MTV Movie Awards and, as of 2010, it remains her most commercially successful film, earning $160 million worldwide as well as an 88% approval rating on Rotten Tomatoes.