 In December 1999, it became his first number one single, holding the top spot for one week.The song was based on Paisley's frequent co-writer and best friend, Kelley Lovelace's stepson McCain Merren, who attended the 2000 ACM Awards as Paisley's guest.According to Lovelace, Paisley said to him, "Let's make a song about you two that will make your wife cry."