Middleton began playing guitar in high school where he enjoyed music by bands like Twisted Sister and AC/DC. He began playing in clubs around his hometown of Brisbane with his first band, "Sonic Tapestry". He formed his second band, "Pirate", with friends from high school. He met "Powderfinger" at a "Pirate" show and they asked him to play with them. Middleton played on all of "Powderfinger's" recordings. While playing and recording with them, he was also writing and recording with "Drag". They have released an EP and studio album.