Early in 1999, Lindsayfilmed another movie. Life-Size — originally a Wonderful World of Disney productionlater released on home video — allowed Lindsay to act with Tyra Banks.
In 2000, Lindsay won therole of "Rose" in Bette Midler's television sitcom, Bette. Aftershooting the pilot episode, the show's producers decided it would be easier onthe crew — most of whom lived near Los Angeles — if filming moved toCalifornia. Lindsay gave up the role to stay in New York, and Los Angeles-areaactress Marina Malota was pegged to take over the role of Midler's teen-ageddaughter. The series was canceled only a few months later, due to saggingratings and the strain on its stars (ironically, Midler had to flycross-country from her New York home to tape her own show).
Walt Disney Picturesannounced on 31 July 2002 that Lindsay had signed on to play Anna Coleman inthe theatrical remake of Freaky Friday. To update another film from its ownvaults, Disney signed Lohan and Jamie Lee Curtis (A Fish Called Wanda) as themother-and-daughter team who wake up one day in each other's bodies. Lohan —who already proved she could fill Hayley Mills' shoes and then some — took on arole that helped propel a young Jodie Foster to stardom. Lindsay also sang thefilm's closing theme, Ultimate, written for the film by songwriters Jeff Coplanand Robert Ellis Orrall.
In September, 2002, Lindsaytook her first step toward fulfilling her lifelong dream of becoming arecording artist when one of the biggest names in music, Emilio Estefan, Jr.,took Lindsay under his professional wing. Estefan Enterprises announced afive-album production deal and the promise of an aggressive effort to"sell" her pop style "with a rock edge" to a major recordlabel.In 2003, Lindsay acceptedthe lead role in Disney's Confessions of a Teenage Drama Queen (originally aNew Line project written for Hilary Duff, who had to pass due to her fullschedule). Filmed in Toronto, Ontario, Canada, and in New York City, Queen wasreleased in theatres on 20 February 2004. Later in 2003, leaving The Mousebehind (for the moment), Lindsay jumped over to Paramount Studios to re-teamwith Freaky director Mark S. Waters for Mean Girls, written by Tina Fey andstarring several members of the cast of Saturday Night Live. Lorne Michaelsasked Lindsay to host SNL as Mean Girls premiered in May, 2004, and she wouldhost the show again a year later.
In 2004, Lindsay signed withCasablanca Records and released her first studio album, Speak. Her firstsingle, Rumors—about a teen celebrity trying to keep her private life out ofthe spotlight—was a Gold Record, and the video was nominated for Best Pop Videoat the 2005 MTV Video Music Awards. Her second album, A Little More Personal(Raw), included the single, Confessions of a Broken Heart (Daughter to Father).In that video, Lindsay's sister, Aliana, made her acting debut.