What Music Video Is This Picture From?

This scene from a late 2000s music video comes from the end of the three-verse song. The old woman is a key player throughout this traditional country singer's story, as is the young boy she's dancing with. Do you recognize them? 

The video is best known for the costume changes this normally reliable country singer makes in the four-minute song. We get to see him in '50s garb and with a '70s hippy look before everyone flashes forward to modern times. Click the button below to find out if your guess is right and to see more country music video trivia.