Hannah Montana Season 1 Episode 12

Miley thinks she is holding her Dad back from his dream of singing.

Title: On The Road Again

Hannah befriends Maddie Fitzpatrick at the Tipton, who informs her on how famous Robbie Ray once was and claiming Hannah's "holding him back". This makes Miley feel guilty for forcing him to end his own singing career to begin Hannah's, and vows to get her father back on track.
Title reference: "On the Road Again" by Willie Nelson.