Kenny Chesney chose Grace Potter as his duet partner for “You and Tequila” after an unexpected moment of inspiration while listening to music in the Virgin Islands. The 2011 song, which compares a difficult romance to an unhealthy drinking habit, went on to receive Grammy nominations and became a notable collaboration between the two artists.

Chesney had initially heard demos of the song by its writers and asked friend Tim Crackle to record a male-vocal version, but felt it needed the right female voice. After Crackle’s demo played on shuffle, Potter’s song “Apologies” came on next, prompting Chesney to contact her; Potter had written that earlier song about an emotionally complicated relationship that began when she was 18. The pair’s recording of “You and Tequila” was nominated for Best Country Song and Best Country Duo/Group Performance.