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Cherry's film debut was in "Friends with Money". He appeared as Nick Daley in "Night at the Museum" and "", 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. 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 drama "House", and in an episode of Fox's crime drama "Bones". He appeared in "The Sorcerer's Apprentice" as 10-year-old David Stutler.