Lindsay Lohan's Path to Playboy

The Daily Beast, Wednesday, October 26, 2011, 11:31pm (PDT)

By Marlow Stern

• "You will never see me in a nude scene. Then there's no mystery for my private life."

  RELATED ON THE DAILY BEAST: Check out celebs who faked being married

  Lindsay Lohan uttered those famous last words in a 2005 interview with Access Hollywood. In those halcyon days, the teen actress was promoting the Disney family film "Herbie: Fully Loaded" -- her anticipated follow-up to the zeigeisty 2004 teen comedy "Mean Girls," which, following the blockbuster success of 2003's "Freaky Friday," had cemented her status as America's Sweetheart.

  Just six years later, Lohan more closely resembles America's vindictive ex. With her movie roles all but dried up, the actress who used to command up to $7.5 million per role is currently playing janitor in a morgue 16 hours a day as part of her court-mandated probation. And on Nov. 2, the oft-beleaguered starlet will be in court facing 18 months in prison for violating probation in her shoplifting case. With her finances allegedly dwindling and facing serious jail time, the actress reportedly has decided to pose nude -- showing full frontal -- in Playboy magazine for close to $1 million. How did one of Hollywood's brightest young talents fall so far?

  Back in late 2004, around the time she swore against nudity, was when the trouble started. Lohan was at the height of her fame, having garnered critical and commercial acclaim for 2003's "Freaky Friday," which grossed more than $160 million worldwide, and the Tina Fey-penned 2004 comedy "Mean Girls" -- her first non-Disney film -- which was quickly hailed as that generation's "Clueless." She returned to Disney for her next project, "Herbie: Fully Loaded," and during filming was hospitalized with a kidney infection brought on by stress. Around that time, Lohan experienced a bad break-up with her first serious boyfriend, "That 70's Show"'s Wilmer Valderrama, and her parents -- Dina and Michael Lohan -- were having problems of their own, eventually separating for good in 2005.

  RELATED ON THE DAILY BEAST: ScarJo's many men

  A notorious photograph was snapped in 2005, while she was promoting "Herbie," showing Lohan looking emaciated. The picture caused such an uproar that Lohan was removed from the film's poster since she bore little resemblance to the healthy-looking redhead depicted. In a 2006 interview with Vanity Fair, Lohan revealed that her shrinking frame was due to bulimia, and she was experimenting with drugs at the time. According to the story, when she hosted "Saturday Night Live" in May 2005, her "Mean Girls" co-stars Amy Poehler and Tina Fey attempted an intervention on Lohan, worried she was in bad shape.

• "Amy was good and tough on her," Fey told Vanity Fair, "saying, 'You're too skinny ... I'm not going to ask you why, but you're too skinny and I don't like it.'" "They sat me down," Lohan said, "literally before I was going to do the show, and they said, 'You need to take care of yourself. We care about you too much, and we've seen too many people do this,' and I just started bawling. I knew I had a problem and I couldn't admit it."

  The paparazzi began hounding Lohan, and in Nov. 2006, a rogue paparazzo struck her car, resulting in minor injuries to the actress. Despite her off-screen foibles, "Herbie: Fully Loaded" performed well, earning $144 million worldwide, resulting in a reported $7.5 million payday for her follow-up, 2006's "Just My Luck." (By comparison, this is the same amount that "Twilight" teen idol Taylor Lautner reportedly was paid for the upcoming "Stretch Armstrong" movie). That film tanked, however, earning just over $17 million in North America and earning Lohan her first Golden Raspberry nomination for worst actress. She rebounded slightly, however, with bit parts in the acclaimed ensemble dramas "A Prairie Home Companion," the great Robert Altman's final film, and Emilio Estevez's Bobby, about the assassination of Robert F. Kennedy.

  RELATED ON THE DAILY BEAST: Supermodels who are now moms

  The trouble continued in 2006, however, while Lohan was shooting the drama "Georgia Rule," opposite Jane Fonda. After she was hospitalized during filming for exhaustion, the film's producer, James G. Robinson, fired off an angry letter to Lohan that read: "You and your representatives have told us that your various late arrivals and absences from the set have been the result of illness; today we were told it was 'heat exhaustion.' We are well aware that your ongoing all night heavy partying is the real reason for your so-called 'exhaustion'… You have acted like a spoiled child and in so doing have alienated many of your co-workers and endangered the quality of this picture." That year, Lohan started attending Alcoholics Anonymous meetings and, in early 2007, checked herself into rehab for 30 days.

  In May 2007, just two weeks after "Georgia Rule" was savaged by critics and audiences alike, Lohan was convicted of misdemeanor DUI, serving 45 days rehab. Weeks after being released, she lost control of her car and crashed it. When police arrived, they found her intoxicated, with a small amount of cocaine in her pocket. She was charged with felony possession of cocaine, misdemeanor DUI, and driving with a suspended license, and again sentenced to rehab, this time for two months. During this time, her abysmal 2007 film "I Know Who Killed Me," a sleazy, low-budget thriller starring Lohan as a stripper with multiple-personality disorder, opened to just $3.5 million its first weekend, and earned her a Razzie Award for Worst Actress. That August, Lohan pleaded guilty to misdemeanor cocaine use and DUI, eventually serving 84 minutes in jail. "It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs," Lohan said in a statement.

• RELATED ON THE DAILY BEAST: Celebs who throw first pitches at the World Series

  Following a yearlong hiatus, in May 2007 Lohan guest starred in a four-episode arc of the ABC series "Ugly Betty," and posed topless in a bizarre recreation of Marilyn Monroe's final photo shoot with photographer Bert Stern in New York Magazine. Of the spread, The New York Times wrote, "the pictures ask viewers to engage in a kind of mock necrophilia," adding that, "At 21 [Lohan] seems even older than Monroe, who was 36 in the originals." Around that time, Lohan offered to host campaign events to help drum up support for Barack Obama's 2008 presidential campaign-- campaign staffers, however, declined the offer, with one telling The Chicago Sun-Times that Lohan "is not exactly the kind of high-profile star who would be a positive for us."

  Around this time, Lohan turned down a potential comeback role as The Wolf Pack's stripper accomplice in the 2009 summer blockbuster "The Hangover", according to the New York Daily News. Despite her agent pushing hard for her to accept the part, Lohan believed that the script "had no potential," and Heather Graham assumed the role. The film went on to gross more than $277 million in North America alone, setting a then-record as the highest grossing R-rated comedy of all-time (before it was eclipsed by its recent sequel).

  RELATED ON THE DAILY BEAST: People who've hooked up on 'Idol'

  Instead, Lohan starred in the 2009 comedy "Labor Pains" after it took ages getting her insured for the film, according to The New York Daily News. The movie never received a theatrical release, and was downgraded to a TV movie on ABC Family. "[Labor Pains] never shakes free of the heavy baggage Ms. Lohan brings to the role," wrote the New York Times' Alessandra Stanley. During this period, from 2008 to 2009, Lohan engaged in a passionate romance with DJ Samantha Ronson, with their frequent public spats providing ample gossip fodder.

  After a disastrous stint as the artistic director for high-end fashion house Emanuel Ungaro in late 2009, with The New York Times calling Ungaro's decision, "something akin to a McDonald's fry cook taking the reins of a three-star Michelin restaurant,” the fallen star got into more legal hot water. On July 6, 2010, a judge sentenced her to 90 days in jail for violating her probation -- she had skipped mandatory DUI progress report hearings -- of which she served 14 days behind bars, followed by 23 days in rehab. While in rehab, Lohan starred in Robert Rodriguez's campy B-movie "Machete" as an oft-nude, drug-taking socialite—poking fun at her tabloid image -- and was also dropped from the Linda Lovelace biopic Inferno, whose script made the 'Black List' of the best unproduced screenplays, and replaced by Malin Akerman due to problems insuring the troubled star, the film's producers told E! Online.

• Even more legal problems ensued when, on Sept. 24 of that year, her probation was revoked for her failing a drug test. "Substance abuse is a disease, which unfortunately doesn't go away over night. I am working hard to overcome it," she wrote on her Twitter. She served a day in jail and then checked into Betty Ford for three months of rehab. Then, in January 2011, she was caught allegedly stealing a necklace from a jewelry store. On Feb. 9, she was sentenced to 120 days in prison for the crime -- of which she served only 35 days under house arrest due to jail overcrowding -- 360 hours of community service at the Downtown Women's Center in L.A., and 120 hours at the L.A. County morgue. Because of her legal troubles, she reportedly was dropped from the role of Victoria Gotti in the mob biopic "Gotti: Three Generations," starring Al Pacino and John Travolta.

  RELATED ON THE DAILY BEAST: Hollywood's new BFF

  In July, Lohan visited a judge for a progress report and claimed she couldn't continue her court-mandated psychological treatment because she was broke, according to The Huffington Post. And on Oct. 19, Lohan, having failed to attend her community-service sessions at the Downtown Women's Center, had her probation revoked and was -- quite embarrassingly -- removed from the courtroom in handcuffs, reported the Los Angeles Times. Lohan must complete 16 hours a day of community service at the L.A. County morgue before her next hearing on Nov. 2, where she faces up to 18 months in jail for violating her probation.

  Now, the apparent coup de grâce—a cash-strapped Lohan reportedly has decided to do full frontal nudity in an upcoming issue of Playboy for close to $1 million. According to reports, she recently completed the four-day shoot -- with her Momager Dina's blessing -- and even brought her 17-year-old sister, Ali, along for it. Lest we forget, this is all happening while her disturbed father, Michael Lohan, is facing domestic-violence charges.

  While posing for Playboy does not necessarily symbolize the end of the talented Lohan's film career, the last notable Hollywood star to pose nude in its pages was Denise Richards in 2004, and, while she possessed far less natural talent than Lohan, the former Bond girl's film career never recovered. Drew Barrymore famously graced Playboy's pages in 1995 during her bad-girl phase, but soon rebounded with roles in "Scream" (1996) and "The Wedding Singer" (1998). And then up-and-coming actress Charlize Theron posed nude for Playboy in 1999, and went on to win the Best Actress Oscar in 2004 for "Monster." While none of these women did full-frontal like Lohan allegedly does, let's hope that the 25-year-old actress turns her career around like Barrymore did -- reminding us of her immense talent -- instead of falling for a self-described "Vatican assassin warlock," like Richards.

• RELATED ON THE DAILY BEAST: Celebs who also have cookbooks