Khaleef Chiles became one of American Idol's season 1 top 24 final contestants at the age of 20. Khaleef Chiles is from Plainfield, NJ. Khaleef Chiles was not the winner of American Idol, far from it. Khaleef Chiles didn't even make the top 10 list during season 1. However, Khaleef Chiles was amongst season one's best of the rest.