Cherry's film debut was in Friends with Money. He appeared as Nick Daley in Night at the Museum and Night at the Museum: Battle of the Smithsonian, and as Travers McLain in Desperate Housewives. Cherry did not reprise his role as Nick Daley in the third Night at the Museum film installment, with Skyler Gisondo taking over the role. He also appeared on Fox's short-lived series Head Cases. He appeared in an episode of Criminal Minds, as a patient's son in Fox's medical dramaHouse, and in an episode of Fox's crime dramaBones. He appeared on The Sorcerer's Apprentice as 10-year-old David Stutler.