Rascal Flatts (yay!!!)
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Rascal Flats Tom Cochrane did it in the 90s
The theme song is "Family Tree" by Rain Perry. You can find it on youtube, but she has not recorded it on CD yet.
The song With Me was recorded by Sum 41. It was recorded in 2007 and appeared on the Underclass Hero album. The song was first performed live in January 2008.
Im pretty sure it was sung by the band The highway men
Ventura Highway