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Massey lived in Missouri until he was discovered by a talent scout at the shopping mall with his older brother Christopher Massey, who played Michael Barret on the Nickelodeon show, Zoey 101. His parents relocated in Atlanta, Georgia due to some issues in Missouri so they headed back where Kyle was born. Massey and his brother starred in many Broadway shows and earned several nominations from the "Outstanding Young Performer in Live Theatre" award. Massey also appeared in several commercials for Burger King and Disney. He became an overnight sensation when he was the role of Cory Baxter in the Disney Channel series That's So Raven and the spin-off Cory in the House. The two shows were the networks most viewed and received the highest ratings. He also starred as Marvin Washington in Focus on the Family's "Adventures in Odyssey".

His big break came after he was cast in the Disney sitcom That's So Raven, where he starred as Cory, Raven Baxter's stubborn younger brother who is constantly at odds with her. Kyle also stars in the Disney show Cory in the House, a spin-off of That's So Raven in which Cory's father, Chef Victor, becomes the White House chef, and he and Cory move into the White House.He also starred in the 2005 Disney Channel Original Movie Life Is Ruff. His rap single, "It's a Dog", was included in the movie Life Is Ruff and on the CD soundtrack for the Disney Movie Underdog. He also starred in a music video for Yin Yang Yo, which premiered in September 2006.Massey's other significant roles on the Disney Channel have included voiceover work for the Disney Channel animated series American Dragon: Jake Long. Massey was cast as Huntsboy 88 on the series. He also competed in the first ever Disney Channel Games. He was on the Green Team, along with Disney actors Lucas Grabeel, Ashley Tisdale, Miley Cyrus, Emily Osment and Mitchel Musso, and was voted MVP for the Rock, Paper, Scissors challenge. Kyle was also asked back for Disney Channel Games 2007 and was the captain of the Yellow Team. Kyle is now back at the DC Games for the second time on the yellow team. Kyle also skates like his role in Life is Ruff. He was voted one of Aol's "Top Tween (or teen) Acts". Most Recently Massey had his own show, Cory in the House, a spin-off of That's So Raven. Cory in the House follows Cory Baxter and his dad Victor Baxter (Rondell Sherdian) moving to Washington D.C. when Victor Baxter was offered to be the head chef in the white house kitchen. He makes 2 new friends Menna Paroom (Maiara Walsh) and Newt Levingston (Jason Dolley). And also a new pest the Presidents daughter Sophie (Madison Pettis) and the head of the Country himself President Richard Martinez (John D'Aquino). The show started in 2007 and has been canceled as of September 2008.

DreamWorks Animation announced Kyle Massey portrayed Jim’s best friend, Leo, in the movie version of Tom and Jerry.

Although Massey has released singles for various soundtracks and has starred in numerous music videos for Disney, he stated in an interview with Disney Adventures magazine that he did not plan on recording an album, since he "can't sing" and does not think that he would be a successful mainstream rapper. He sang a song for the movie Underdog.

Massey has appeared in the Disney Channel Holiday soundtrack and the Shaggy Dog soundtrack where he performed Who Let The Dog Out. He also sang the theme song for Cory in the House. Massey also raps a song called "It's a Dog" on the Life is Ruff soundtrack. He also guest starred on The Electric Company's first episode Skills as Coach.