Aiming to become a triple threat—actor, singer and dancer, similar to Ann-Margret and Marilyn Monroe—Lohan began showcasing her singing through her acting.[25] For the Freaky Friday soundtrack, she sang the closing theme, "Ultimate",[6] as well as recording four songs for the Confessions of a Teenage Drama Queen soundtrack. Producer Emilio Estefan, Jr. signed Lohan to a five-album production deal in 2002.[6] Two years later, Lohan signed a recording contract with Casablanca Records, headed by Tommy Mottola.[26]
In 2004, Lohan starred in two lead roles. The first, Confessions of a Teenage Drama Queen—Lohan's first role in a film that was not a remake[6]—earned a domestic box office total of $29 million, with Brandon Gray of Box Office Mojo commenting that it was "well above expectations as it was strictly for young girls".[27] The film overall, however, did not meet with critical acclaim.[28] Robert K. Elder of Metromix wrote that, "though still a promising star, Lohan will have to do a little penance before she's forgiven for Confessions".[29]
The teen comedy Mean Girls was Lohan's first movie independent of Disney. The film was a critical and commercial success, grossing $129 million worldwide and, according to Brandon Gray, "cementing her status as the new teen movie queen",[27][30][31] while Steve Rhodes wrote that "Lohan dazzles us once more. The smartly written script is a perfect match for her intelligent brand of comedy."[32] Lohan received four awards at the 2004 Teen Choice Awards for Freaky Friday and Mean Girls, including Breakout Movie Star.[33] Mean Girls also earned her two awards at the 2005 MTV Movie Awards, Best Female Performance and Best On-Screen Team along with several other cast members.[34]
Lohan, then 17, became the youngest-ever host of the MTV Movie Awards in 2004.[35] Following Mean Girls, which was scripted by Tina Fey and featured several alumni of Saturday Night Live, Lohan hosted the show three times between 2004 and 2006, as well as hosting the 2006 World Music Awards.[36]
Speak, Lohan's debut album, was released in December 2004, peaking at number four on the Billboard 200[37] and earning Platinum certification by early 2005.[6] Lohan cowrote six of the twelve songs on the album. The album was praised by Linda McGee of RTÉ, who awarded it 4 out of 5 stars and commented that "Speak opens with all the raw emotion and teenage angst that you'd expect from an artist of Lohan's age" and that, "while her vocals are not sensational, their gritty edge keeps Lohan more than afloat throughout this album"[38] as well as comparing the album to the early music of Avril Lavigne.[38] Allmusic, however, awarded it 2 out of 5 stars and claimed the album "feels more like a byproduct of an overdriven, overamplified celebrity culture than an actual album".[39] Though primarily a pop album, Speak was introduced with the single "Rumors". Described by Rolling Stone as "a bass-heavy, angry club anthem",[40] "Rumors" details Lohan's complaints with the paparazzi[41] and eventually earned a Gold certification in the United States.[42]
While shooting Herbie: Fully Loaded in 2004, Lohan was hospitalized with a kidney infection brought on by stress in her personal life and of recording her first album while the film was in production, prompting Vanity Fair to label it Lohan's "first disastrous shoot".[43] The magazine also described how Lohan terminated the promotional tour and was de-emphasized on the movie poster due to "un-Disney-like behavior".[43] Lohan began dating actor Wilmer Valderrama in 2004, guest-starring in an episode of That '70s Show, of which Valderrama was a regular.[44] According to Vanity Fair, the breakup with Valderrama contributed to Lohan's issues during the shooting of Herbie: Fully Loaded.[43]
With Mean Girls, Lohan's public profile was raised significantly and paparazzi began following her.[45] She spent several years living out of hotels in Los Angeles, of which two years were spent at Chateau Marmont. In late 2007, after settling down in more permanent residence, she explained that she spent so much time in hotels because she "didn't want to be alone" but that "it wasn't a way of life ... not very consistent."[46][47][48] Lohan has had a series of car accidents that have been widely reported, with minor crashes in August 2004,[49] October 2005,[50] and November 2006, when Lohan suffered minor injuries because a paparazzo who was following her for a photograph hit her car. Police called the crash intentional, but prosecutors said there was not enough evidence to file criminal charges.
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