Lohan is arrested on suspicion of drunk driving in Santa Monica, Calif. The 21-year-old, who had cocaine in her possession while wearing an alcohol detection anklet, is booked for DUI, possession of cocaine, transporting a narcotic into a custody facility and driving on a suspended license. The arrest comes 11 days after she completed a 45-day rehab stint, and five days after she surrendered and was formally booked on misdemeanor charges stemming from a May car crash.
Lohan checks out of Utah's Cirque Lodge Treatment Center with her estranged father, Michael (who she reunited with while in rehab) at her side. The 21-year-old also returns to the set of her tango-themed film, Dare to Love Me, and begins her community service and serves 84 minutes in jail as part of the plea deal for her two DUIs. She is also ordered to spend spend two days in a morgue and two days working in an emergency room to illustrate the potentially fatal consequences of drinking and driving.
Lohan is spotted around town with DJ BFF Samantha Ronson. Photographed holding hands (and even kissing), a source tells PEOPLE the longtime friends are actually ''together''. In March 2009, they call it quits, with Lohan reportedly writing messages on her Twitter page alleging Ronson's infidelity and drug use were the reasons behind their split.
After nabbing a record number of Razzies for her 2007 thriller I Know Who Killed Me, Lohan guest-stars on ABC's Ugly Betty, playing a mean girl from Betty's (played by America Ferrera) high school days. Lohan makes her Ugly debut in the second season finale and returns for a handful of episodes the following season.
After pulling a no-show in court, Lohan is ordered to wear a SCRAM alcohol-monitoring bracelet, her second in three years, and is subject to weekly random drug testing. The device is set off two weeks later at an MTV afterparty, landing the actress back in jail, where she serves 13 days, before completing a 23-day, court-ordered stint in rehab.
Weeks after leaving rehab, Lohan fails at least one drug test, landing the actress back in court. "This was certainly a setback for me but I am taking responsibility for my actions and I'm prepared to face the consequences," she Tweets. On Sept. 24, a judge orders Lohan back to jail – her third and possibly longest stint – until another hearing on Oct. 22, but the actress wins an appeal, leaves jail later that night, and returns to rehab.
Lohan is accused of allegedly stealing a $2,500 necklace that went missing from a Venice, Calif., store, landing her back in court on a felony grand theft charge. The actress, who has a history of theft allegations, says, "I would never steal…I was not raised to lie, cheat, or steal." In April, a judge finds Lohan in violation of probation and sentences her to four months in jail and 480 hours of community service.
Lohan, 25, violates probation in both her DUI and necklace-theft cases, landing her back in jail for the fifth time. Sentenced to 30 days behind bars, which she must begin serving on Nov. 9, the actress admits she missed too many community service appointments.
The troubled actress appears on the cover of Playboy for a nude pictorial – an ode to her icon Marilyn Monroe. "I have no idea why there is this fascination with everything I do," Lohan says of the issue and spread being leaked online. Looking on the bright side, Hefner Tweets that the issue "will make the perfect Christmas issue for men in your life."
Following years of personal and professional mishaps, Lohan pokes at her troubles on Saturday Night Live, which she hosts for the fourth time to rave reviews. Following her appearance, the actress makes a cameo on Glee and takes on an iconic role, playing the late Elizabeth Taylor in Lifetime's biopic Liz & Dick.
BIOGRAPHY (top to bottom): Courtesy Santa Monica Police Department; Flynet; Bauer-Griffin; AP; David McNew/Getty; Splash News Online; Flynet; Krista Kennell/Sipa; Playboy; INF