In it, the male narrator addresses a female, inviting her to climb up into his four-wheel drive truck and telling her that he can take her wherever she wants, because he is a "country boy".

"[2] In late September 2008, Jackson announced on his official YouTube channel that he was holding a music video contest for "Country Boy".

The viewers, or YouTubers, were asked to create a simple video no longer than five minutes driving around with a girlfriend.

The contest ended on October 6, 2008, and was won by Clay Ashley, Dan Hair, and Mark Trotter of Sioux City, Iowa.

[3] Before the official video, television network CMT aired a live music video which featured Jackson performing the song with Brad Paisley, Dierks Bentley and George Strait on the CMT Country Giants special.