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.
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 début 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.