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
Young Artist Award for Outstanding Young Performer in Live Theatre for his role as Young Simba in The Lion King. Massey had his first starring role as
Michael Barret in the 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.
Zoey 101 was nominated for an Emmy for Outstanding Children's Program in 2005. in June 2008 Massey is the older brother of
Kyle Massey, star of Disney shows
Cory in the House, ''
That's So Raven, and Fish Hooks. He guest-starred alongside his brother in a That's So Raven
episode titled "Five Finger Discount". The Massey brothers have also had small roles on the sitcom The Parkers, appeared together on The Steve Wilkos Show'', and released music together as the Massey Boyz. On January 12, 2023,
Jamie Lynn Spears announced that production had begun on a sequel film, titled
Zoey 102, scheduled to premiere in 2023, on
Paramount+, with original series cast members Spears, Massey, Sean Flynn,
Erin Sanders, Matthew Underwood,
Jack Salvatore Jr., and
Abby Wilde reprising their roles. Additionally,
Nancy Hower was set to direct, with Spears attached as an executive producer. Production began in January 2023 in
North Carolina. The film was released on
Paramount+ on July 27, 2023. ==Personal life==