Lovett claims that this song is based on a true story. He once tried to ride a pony across a pond [Hopefully it was not a deep pond and the pony was never uncomfortable. As far as we know, Lovett is good with animals and children], and thought it would be easier if he had a boat.
This is the lead track off of Lovett's second album. This album expanded his audience beyond just country music, while songs like this helped to retain some of that crowd.