Lewis began making television appearances while in his late teens, with guest starring roles in Boston Public (2000), The Guardian (2001), and American Dreams (2002), among others. His debut feature film performance premiered in 2004, in New Line Cinema's Raise Your Voice, and he followed that up with Miramax Films' Underclassman in 2005. He co-starred as Pearce Chase, one of five siblings on the Fox series Quintuplets, and appeared in the movie Raise Your Voice (2004) alongside Hilary Duff. He guest starred in four episodes of the Nickelodeon television series Drake & Josh as Scottie, one of Drake's bandmates, and from 2005 to 2006, he played Dennis "Chili" Childress on The O. C. . Lewis also had a guest spot in the third episode of Smallville season 5.