Early in his life, Till's parents became aware of his ability to imitate voices and characters. Joy Pervis discovered Till while he was attending a local acting class where his mother had enrolled him. When he was 10, he started doing commercials as well as appearing in print. At the age of 12, he was cast in The Adventures of Ociee Nash in which he played Harry Vanderbilt, the bully of the main character. In 2004, Till played the role of Jay in the feature film Lightning Bug which filmed in Fairview, Alabama. His first major movie role was Jack Cash, the older brother of Johnny Cash, who died in a sawmill accident, in the biographical movie Walk the Line. After Walk the Line, Till was featured in a number of independent movies and films for Lifetime Television. In 2008, Till auditioned for Hannah Montana: The Movie starring Miley Cyrus and he landed the role of Travis Brody. In an interview, Till said that prior to filming he had actually never ridden a horse before. Till further stated that he does not have any current plans for another Disney movie. He worked alongside action film actor Jackie Chan in the movie The Spy Next Door, in which Till plays the role of a Russian spy. He also starred in Taylor Swift's music video "You Belong with Me". He was in an episode of House, and on Leo Little's Big Show along with Emily Osment.