Chilton first came on the scene in 1967 as lead of The Box Tops, with the hit "The Letter"; they went on to have several other hits including "Cry like a Baby" (1968).
In 1971 he formed Big Star with his friend Chris Bell. Since that time he has performed both as a solo artist and in various lineup of Big Star and the Box Tops. The current (2003) lineup includes Jon Auer and Ken Stringfellow of The Posies.
Among Chilton's songs is "In the Street", which became the theme song for That '70s Show.
His producing credits include The Cramps' Songs the Lord Taught Us.