"Everyday Is a Winding Road" is the second single from American singer and songwriter Sheryl Crow's 1996 eponymous album. Neil Finn, lead singer of Crowded House, provides backing vocals.[2] Paul Hester, another member of Crowded House, was the inspiration for the song.[2] The song was released in the United Kingdom in November 1996 and was released in the United States the following year. 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.[3] 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.