Hoping to become a "triple threat" (actor/model/singer) like her idol, Ann-Margret, Lohan began by showcasing her singing talents through her films. For the Freaky Friday soundtrack, she sang the closing theme, "Ultimate"; she also recorded four songs for the Confessions of a Teenage Drama Queen soundtrack.
Lohan's debut album, Speak, was released two years after she signed a production deal with Emilio Estefan, Jr.Producer Emilio Estefan, Jr. signed Lohan to a five-album production deal in 2002. "The minute I heard her sing, I knew she was gifted," he said, "and [she] has an incredible ability to connect with her audience. I am very excited to be working with her." Lohan—who said she was "extremely excited"—added, "I am surrounded by a group of very talented people." Two years later, Lohan signed a recording contract with Casablanca Records, headed by "diva-maker" Tommy Mottola. Her debut album, Speak, was released in December 2004, and peaked at number four on the Billboard 200. By early 2005, it was certified Platinum. Though primarily a pop-rock album, Speak was introduced with the single "Rumors", described by Rolling Stone as "a bass-heavy, angry club anthem". Its sexually suggestive video reached number one on MTV's TRL and was nominated for Best Pop Video at the 2005 MTV Video Music Awards. "Rumors" eventually earned a Gold certification in America.
"[W]ith just two hit films under her belt", wrote Stephen Thomas Erlewine of All Music Guide, "Lohan decided it was time to turn [herself] into a multimedia, cross-platform star ... and so Speak was recorded quickly and rushed into the stores". He called her music "a blend of old-fashioned, Britney-styled dance-pop and the anthemic, arena rock sound pioneered by fellow tween stars Hilary Duff and Ashlee Simpson. [However,] Lohan stands apart from the pack with her party-ready attitude and her husky voice".
In December 2005, her second album, A Little More Personal (Raw), debuted at number 20 on the Billboard 200 chart, but fell under the top 100 within six weeks. Reviews were unfavorable; critics wondered why an album in which Lohan poured out her heart came across instead as a "slick pop production." Slant magazine called it "contrived ... for all the so-called weighty subject matter, there's not much meat on these bones." Still, A Little More Personal (Raw) was certified Gold on January 18, 2006. The music video for the album's first single, "Confessions of a Broken Heart (Daughter to Father)"—directed by Lohan and featuring the acting debut of her sister, Ali—was a dramatization of the pain Lohan says her family has suffered at the hands of her father. She said "It's kind of offensive" but "I hope he sees the positive side of the video rather than the negative."
Universal Music Group moved Lohan from Casablanca to Motown Records in February 2006] In March, she told OK! magazine that she was writing lyrics for her third album, which she called "different [from] the first two". The November 2006 edition of In Style reported a Christmas 2006 release, but it was pushed back.
In a May 2007 interview in Nylon Lohan stated that she plans to record her third studio album in August 2007, saying "I want to do a tour like Madonna. [...] I want to do what Britney was doing. I want to work with Pharell, Timbaland, and Justin Timberlake.".
Albums
Speak (2004)
A Little More Personal (Raw) (2005)
Singles
2004: "Drama Queen (That Girl)"
2004: "Rumors"
2005: "Over"
2005: "First"
2005: "Confessions of a Broken Heart (Daughter to Father)"
2005: "I Live for the Day"
Soundtracks
2003: Freaky Friday
2003: The Princess Diaries 2: Royal Engagement
2004: Confessions of a Teenage Drama Queen
2004: That's So Raven
2005: Herbie: Fully Loaded
2006: A Prairie Home Companion