The single was well-received on the radio and peaked at number 11 on the US '' Billboard '' Hot 100 . It also peaked at number 12 on the UK Singles Chart and became Crow 's fourth and final number-one single in Canada . The song earned a nomination for Record of the Year at the 1998 Grammy Awards but lost to " Sunny Came Home " by Shawn Colvin . A music video for this song was directed by Peggy Sirota and filmed in New York City in sepia . It features a toy airplane flying from person to person throughout the city
1998 Grammy Awards
40th Annual Grammy Awards
Everyday Is a Winding Road