Massey started his acting career at a young age, appearing in commercials for Cap'n Crunch and Pop Tarts. He also has made a guest appearance on Punk'd. He won 2002's Outstanding Young Performer in Live Theatre award for his role as Young Simba in The Lion King (LA). Massey received an Emmy nomination in 2006 for Zoey 101. He stayed for the whole series and all 4 movies. Massey has appeared in several commercials with his brother for Burger King, Disney and Pepsi. Christopher is also a singer/rapper and song writer and music producer for several big names in the music industry. Massey earned his first starring role as Michael Barret in the Emmy-nominated Nickelodeon television show, Zoey 101. When the show debuted in January 2005, it drew a larger number of viewers aged 9–14 than any premiere on the network in the preceding eight years. He stars as Michael Barret in the series which follows the daily life of Zoey Brooks, played by Jamie Lynn Spears, one of the first girls to pass admissions for a formerly all-boy boarding school, called Pacific Coast Academy. Zoey 101 was nominated for a 2005 Emmy for Outstanding Children's Program. Massey is the older brother of Kyle Massey, who starred in the Disney sitcom series Cory in the House, That's So Raven, and is a voice actor in Fish Hooks. He has guest starred alongside his brother on a That's So Raven episode "Five Finger Discount". Massey and his brother have had small roles on the sitcom The Parkers.
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