Earles plays Miley Stewart/Hannah Montana’s (Miley Cyrus) older brother, Jackson Stewart, in the Disney Channel Original Series Hannah Montana. He is her dorky, annoying brother. He guest starred twice on Phil of the Future, as Grady Spaggett, an advanced math student. Earles was in the 2006 Disney Channel Games on the Blue Team and in the 2007 Disney Channel Games on the Red team.

Earles played a nerdy card gamer that was friends with the character Brian Miller, on the sitcom Still Standing. In 2004, he appeared in the movie National Treasure as Thomas Gates, ancestor of Ben Gate (Nicholas Cage). In 2005 Earles played Ernie Kaplowitz in the movie American Pie Presents: Band Camp.

Earles was the co-host of Disney Channel’s Sing-Along Bowl-athon (Disney Channel’s 2006 New Year’s Eve special) and the corresponding online voting.^[7]