Chris Applebaum is an American music video director . He has filmed music videos for many famous artists including Rihanna , Hilary Duff , and Britney Spears . Chris Applebaum is an American music video director , who has worked with a diverse range of artists , among them Rihanna , Hilary Duff , The Mighty Mighty Bosstones , Mandy Moore , Natasha Bedingfield , Fountains of Wayne and Britney Spears .