After a couple of years of independent films and TV, Selma Blair began to make her name in late-'90s teen-targeted work. The Michigan-born and educated Blair originally moved to New York to pursue a career as a photographer, but wound up taking acting classes at the Stella Adler Conservatory instead. After being discovered by an agent, Blair played substantial roles in indie films Strong Island Boys (1997), Girl (1998), and Brown's Requiem (1998), and the TV movie No Laughing Matter (1997). She truly arrived, as the proverbial young actress to watch, in 1999 as level-headed New York teen Zoe in the WB sitcom Zoe, Duncan, Jack, and Jane (retitled Zoe in 2000), and more prominently, as the gullible and bumbling Cecile Caldwell in the popular Les Liaisons Dangereuses update Cruel Intentions (1999). Although Cecile played a secondary role in the film's nefarious sexual machinations among rich Manhattan prep schoolers, Blair's attention-getting onscreen kiss with co-star Sarah Michelle Gellar earned the teen seal of approval with an MTV Movie Award for Best Kiss in June 2000. Blair continued her youth movie work as a school drop-out-turned-porn star in the college romantic comedy Down to You (2000). After the cancellation of Zoe, Blair turned her attention again to movies. Though she played the lead in Kill Me Later (2001), Blair had a higher profile supporting role in the hit summer comedy Legally Blonde (2001). As the WASP Harvard law student Vivian Kensington, Blair was the uptight, brunette opposite of Cruel Intentions co-star Reese Witherspoon's pink and blonde Los Angeles princess Elle Woods, initially sneering at her vulgar rival before being won over by Elle's legal smarts and their shared love interest's idiocy. Taking a break from Hollywood froth, Blair also appeared as a co-ed who has a fateful intimate encounter with her writing professor in indie film provocateur Todd Solondz's customarily acidic third feature Storytelling (2001). A role as Elle Woods' (Reese Witherspoon) adversary turned friend in the hit 2001 comedy Legally Blonde found Blair offering an effective ying to star Witherspoon's yang, and subsequent roles in The Sweetest Thing (2002) and A Guy Thing (2003) found her offering a pair of winning supporting performances. Her status as an of-the-moment ingenue was further sealed by her participation, along with such other actresses as Julia Stiles and Mena Suvari, in the newfangled, tasteful 2002 version of the Pirelli Tires Calendar, and in 2004 Blair opted to expand her resume into special-effects laden blockbuster territory with the larger-than-life comic-to-screen adaptation Hellboy.