In May 2008, Lohan made her first screen appearance since I Know Who Killed Me, on ABC's television series Ugly Betty.[133] She guest starred in four episodes, spanning seasons two and three in 2008, as Kimmie Keegan, an old schoolmate of the protagonist Betty Suarez.[133] Lohan made a cameo appearance in the drug themed music video for the May 2008 N*E*R*D song "Everyone Nose".[134]
Lohan has featured in various men's magazines. She was voted tenth on the list of "100 Sexiest Women" by readers of FHM in 2005,[135] while Maxim placed her third on its" Hot 100" list in 2006[136] and first in 2007.[137] In a poll by The Daily Mirror in February 2010, Lohan was voted tenth on a list of "sexiest redheads ever".[138] Lohan has been the face of Jill Stuart, Miu Miu, and Dooney & Bourke, as well as the 2008 Visa Swap British fashion campaign[139][140] as well as being the face of Italian clothing company Fornarina for its Spring/Summer 2009 campaign.[139]
Lohan has a long-lasting fascination with Marilyn Monroe going back to when she saw Niagara during The Parent Trap shoot.[141] In the 2008 Spring Fashion edition of New York magazine, Lohan re-created Monroe's final photo shoot, known as The Last Sitting, including nudity, saying that the photo shoot was "an honor".[141] The New York Times critic Ginia Bellafante found it disturbing, saying "the pictures ask viewers to engage in a kind of mock necrophilia. ... At 21 [Lohan] seems even older than Monroe, who was 36 in the originals ... [and] the photographs bear none of Monroe's fragility".[142]
In 2008, Lohan launched a clothes line, whose name 6126 was designed to represent Monroe's birth date (June 1, 1926). The line started with leggings, before expanding to a full collection, covering 280 pieces as of April 2010.[143][144][145] In April 2009, Lohan released a self-tanning spray under the brand name Sevin Nyne in collaboration with Sephora.[146][147] In September 2009, Lohan became an artistic adviser for the French fashion house Emanuel Ungaro;[148] a collection by designer Estrella Archs with Lohan as adviser was presented in October, receiving a "disastrous" reception, according to Entertainment Weekly and New York.[149][150] Lohan left the company in March 2010.[151]
During the 2008 US presidential campaign, Lohan offered her services to Barack Obama's election effort, including hosting events aimed at young voters; but her offer was declined. An unnamed source within the Obama campaign told the Chicago Sun-Times that Lohan was "not exactly the kind of high-profile star who would be a positive for us."[152] She nonetheless posted MySpace blogs with her opinions on the election, urging voters to support Obama, criticizing media coverage of vice-presidential candidate Sarah Palin, and describing Palin as homophobic, anti-abortion and anti-environmentalist.[153][154][155][156] Lohan had previously expressed an interest in going to Iraq, during the Iraq War in 2006, on a USO tour with Hillary Clinton.[157] Back in 2004, Lohan stated that she did not like to talk about politics in order to avoid alienating any part of her fanbase.[158]
Lohan dated DJ Samantha Ronson in 2008 and 2009.[159][160] Lohan co-hosted club events with Ronson and accompanied her when she was DJ-ing.[161][162] Speaking about her sexual orientation, Lohan has said she is not a lesbian. When asked if she is bisexual, she responded "Maybe. Yeah", adding "I don't want to classify myself."[159] In April 2009, following her break up with Ronson, Lohan appeared in a skit on the comedy website Funny or Die. The self-deprecating video is a spoof of the personal ads on dating website eHarmony.[163] It was viewed 2.7 million times in the first week and received favorable comments from the media.[164]
In the 2009 comedy Labor Pains, Lohan plays a woman who pretends to be pregnant. During the shoot, Lohan's manager worked with the paparazzi to encourage the media to show her working, as opposed to partying.[165] It was originally planned for a theatrical release, but instead appeared as a TV movie on the ABC Family cable channel in July 2009, "a setback for the star" according to Variety.[166][167] The premiere received 2.1 million viewers, "better-than-average" for the channel according to E! Online.[168] Joanna Weiss of The Boston Globe commented that Lohan "looks to be coasting through a part that requires little effort, anyway".[169] Alessandra Stanley of the New York Times said "this is not a triumphant return of a prodigal child star. ... [Labor Pains] never shakes free of the heavy baggage Ms. Lohan brings to the role".[170]
Lohan was a guest judge on US TV style contest Project Runway sixth season premiere episode, which aired in August 2009.[171][172] In December 2009, she spent a week in India working on a BBC Three documentary on trafficking of women and children.[173][174] She appearred in Robert Rodriguez's Machete, for which she was filming in August and September 2009 and which was released on September 3, 2010.[175][176]
In August 2009, Lohan's home was burglarized by The Bling Ring, a group of fashion-motivated burglars whose ringleader considered Lohan to be their ultimate conquest. Video surveillance of the burglary recorded at Lohan's home played a large role in breaking the case, which ultimately led to the arrests of the group's members.
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