continued working on television, guest-starring on Without a Trace as a teen whose boyfriend goes missing, and on Less than Perfect in 2003. In February 2004, she was cast in a pilot for CBS titled Sudbury, about a family of modern-day witches, based on the 1998 film Practical Magic, but the series was not picked up. Dennings had a recurring role on ER from 2005 to 2006 as Zoe Butler, and twice guest-starred in the CSI franchise: first on CSI, as Missy Wilson in the 2004 episode "Early Rollout". Secondly, she played Sarah Endecott on CSI: NY, in the 2005 episode "Manhattan Manhunt". Dennings made her feature film debut in Hilary Duff's Raise Your Voice in 2004 as Sloane, a somber piano student. In 2005, she landed supporting roles as the daughter of Catherine Keener's character in The 40-Year-Old Virgin and as April in Down in the Valley. In 2006, Dennings played a rebellious teenager in the crime comedy film Big Momma's House 2, starring Martin Lawrence. Dennings starred in Charlie Bartlett in 2008, the story of a wealthy teenager (Anton Yelchin) who acts as a psychiatrist among students at his new public high school. She played Susan Gardner, Bartlett's love interest and the daughter of the school's Principal Gardner, played by Robert Downey, Jr.. Dennings appeared in The House Bunny that year, as Mona, a pierced feminist sorority girl. She also starred that year in the teen comedy romance Nick and Norah's Infinite Playlist, with Michael Cera. Dennings played Norah Silverberg, the daughter of a famous record producer. She was nominated for the International Press Academy's Satellite Award for Best Actress for her performance. In September 2008, Dennings was involved in a project to adapt Don DeLillo's novel End Zone as a film. Actors Sam Rockwell and Josh Hartnett were also involved, but the project was not greenlit because of its subject matter of nuclear war was considered too controversial. In 2009, Dennings appeared in The Answer Man, a film about a celebrity author whose manifestos become a sort of new Bible. She also co-starred in the Robert Rodriguez-directed dark children's film Shorts that year. She played Stacey Thompson, the teenage older sister of the protagonist Toe (Jimmy Bennett). Dennings and other rising stars were featured in the August 2009 issue of Vanity Fair, photographed re-enacting scenes from famous Depression-era films. She was shown in a setting from Sydney