Following Just My Luck, Lohan focused on smaller roles in more mature, independent movies.[73] Robert Altman's ensemble comedy A Prairie Home Companion, in which Lohan co-stars with Meryl Streep and Lily Tomlin, had a limited release in June 2006. Peter Travers wrote for Rolling Stone that "Lohan rises to the occasion, delivering a rock-the-house version of 'Frankie and Johnny'".[74] Co-star Streep said of Lohan's acting: "She's in command of the art form" and "completely, visibly living in front of the camera".[75] The Emilio Estevez drama Bobby was released in theaters in November 2006. Lohan received favorable comments for her performance, particularly a scene opposite Sharon Stone.[76][77] As part of the Bobby ensemble cast, Lohan was nominated for a Screen Actors Guild Award and won an award for Ensemble Acting at the Hollywood Film Festival where she also won a Breakout Award for her work in 2006.[78][79] Lohan's next appearance was in Chapter 27 as a John Lennon fan who befriends Mark David Chapman (Jared Leto) on the day he murders Lennon. Filming finished in early 2006, but was not released until March 2008 due to difficulties in finding a distributor.[80][81][82] In May 2007, the drama Georgia Rule, in which Lohan stars alongside Felicity Huffman and Jane Fonda, was released. Owen Gleiberman of Entertainment Weekly wrote that "Lohan hits a true note of spiteful princess narcissism".[83] During filming in 2006, Lohan was hospitalized, her representative saying "she was overheated and dehydrated".[84] At the time Lohan was going through a breakup with restaurant owner Harry Morton.[85] This contributed to her problems on the set according to Allure.[61] In a letter that was made public, studio executive James G. Robinson called Lohan "irresponsible and unprofessional". He mentioned "various late arrivals and absences from the set" and that "we are well aware that your ongoing all night heavy partying is the real reason for your so-called 'exhaustion'."[86] Co-star Fonda later commented that "when she showed up on the set, she was always great."[87]

In 2006, Lohan attended Alcoholics Anonymous meetings.[88] Lohan, who has suffered from asthma since the age of two, is also a smoker.[89][90] In early January 2007, production on the film I Know Who Killed Me was put on hold when Lohan underwent appendix surgery.[91][92][93] Later in the month, Lohan admitted herself to the Wonderland Center rehabilitation facility. Lohan checked out on February 16, 2007 after completing a 30-day stay.[94][95] During the stay she continued shooting the film, returning to the facility at night.[96][97] Shortly thereafter, Lohan withdrew from a film adaptation of Oscar Wilde's A Woman of No Importance, her publicist stating that Lohan needed to "focus on getting better".[98][99] Lohan was replaced in The Edge of Love in April 2007, shortly before filming was to begin, with the director citing "insurance reasons" and Lohan later explaining that she "was going through a really bad time then."[100][101][102]

Lohan was then cast in the film adaptation of the novel Poor Things. On May 26, four days before production was set to start, she was arrested for DUI and subsequently re-entered rehab. The film's producers initially voiced support and production was put on hold.[103][104][105]

Lohan was involved in a traffic accident on May 26, 2007 when she lost control of her car and ran the vehicle up a curb. Beverly Hills police also found what they preliminarily identified as a "usable" amount of cocaine in her car. After receiving treatment for minor injuries, Lohan was arrested on a misdemeanor charge of driving under the influence of alcohol.[106] She subsequently entered the Promises Treatment Center rehabilitation facility, where she stayed for 45 days.[107][108] Upon her release to outpatient care, Lohan was voluntarily fitted with a SCRAM bracelet to monitor her sobriety.[109][110]

On July 24, three weeks before filming was scheduled to resume, Lohan was arrested for a second DUI and again returned to rehabilitation.[111] Ultimately she fell out of the Poor Things project.[112]

On July 24, less than two weeks after leaving Promises, Lohan refused a field sobriety test in Santa Monica and was taken to a police station where her blood alcohol level was found to be above the legal limit. While conducting a search, the police found a small amount of cocaine in her pocket.[109][110][113] Lohan was booked on a felony charge of possession of cocaine and misdemeanor charges of driving under the influence and driving with a suspended license.[113][114] In August 2007, Lohan entered Cirque Lodge Treatment Center in Sundance, Utah for a third stint at rehabilitation, staying until discharge on October 5, 2007.[115] In 2007 Lohan first dated British TV personality Calum Best and then snowboarder Riley Giles, who she met during her third stay in rehab.[116][117]

In the wake of her second DUI arrest, Lohan withdrew from a scheduled appearance on The Tonight Show with Jay Leno in which she had been due to promote I Know Who Killed Me, a low-budget thriller-mystery in which she stars as a stripper with a dual personality.[118] The film premiered to what Entertainment Weekly called "an abysmal $3.5 million".[119] It earned Lohan a dual Razzie nomination for Worst Actress, with Lohan coming first and second, tying with herself.[120]

Hollywood executives and industry insiders commented that it would be difficult for Lohan to find employment until she could prove that she was sober and reliable, citing possible issues with securing insurance.[121][122][123] Robinson, the producer who previously criticized Lohan's work ethic on Georgia Rule, said that he would work with her again if she got the proper medical care, and went on to describe her as "one of the most talented young women in the movie business today."[119]

On August 23, 2007, Lohan pleaded guilty to cocaine use and driving under the influence and was sentenced to one day imprisonment and 10 days' community service. She was also ordered to pay fines and complete an alcohol education program, and was given three years probation. Lohan released a statement in which she said "it is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs".[124] On November 15, 2007, Lohan served 84 minutes in jail. A sheriff spokesman cited overcrowding and the nonviolent nature of the crime as reasons for the reduced sentence.[125] The probation was extended by an additional year in October 2009, following several instances in which Lohan failed to attend the court-ordered substance abuse treatment classes.[126]

Following a switch to Universal Motown, Lohan began working on a third album, tentatively titled Spirit in the Dark, in late 2007 and released "Bossy" in May 2008.[127][128][129][130] In November 2008, Lohan stated that work on the new album had stalled and that she wanted to avoid the stress of working on movies and music at the same time.[131] In February 2010, Ne-Yo, with whom Lohan had been collaborating, stated in an interview, "We were doing some stuff and then it just fell off and hasn't got back on. I'm not gonna hold my breath."

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