Massey began his acting career at a young age, appearing in commercials for Cap'n Crunch, Pop Tarts, and McDonalds, among others. He also has made a guest appearance on Punk'd. He won 2002's Outstanding Young Performer in Live Theatre award.[citation needed] Massey received an Emmy nomination in 2005 for Zoey 101. He stayed for the whole series and all 4 movies. Massey has appeared in several commericials with his brother for Burger King, Disney and Pepsi.

Massey became an overnight sensation when he was cast in the Emmy-nominated Nickelodeon television show, Zoey 101. The show has been the networks highest rated and most viewed for 3 years.

Massey garnered 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.[1] Spears stars as 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 stars in the Disney sitcom series That's So Raven and Cory in the House. He has guest starred alongside his brother on a That's So Raven episode called "Five Finger Discount". Both Massey and his brother have had small roles on the sitcom The Parkers. 2006, he was named one of Teen People's "25 Hottest Stars Under 25", the list also included Zoey co-star Jamie Lynn Spearsand his brother.