“Everyday Is a Winding Road” by Sheryl Crow

On “Everyday Is a Winding Road”, Sheryl Crow comes off as being overtaken by a wandering spirit. And the highlight of her journey is being picked up while on the hitchhiking circuit by “a vending machine repair man”. Dude apparently impresses her with his “intellectualism”, to the point where the vocalist is willing to follow him on the open road. 

It’s not abundantly clear if they hook up romantically, but what is obvious is that they become friends, i.e. the trucker telling Sheryl about his daughter.

And it has been noted that his character was based on the late Paul Hester, who was very much alive at the time this song came out and a former member of a band called Crowded House. This was early in Sheryl Crow’s career, when she was opening for said group, even though most of us probably never heard of them. But in any event it’s like Paul up and left one day, dropping the line “every day is a winding off” to rationalize his free-spirited departure. But again said character is only based on him (not being Hester himself) as for instance he apparently didn’t go around fixing vending machines.

Song’s Title (“Everyday Is a Winding Road”)

And concerning the titular phrase, it is seemingly meant to point to the ideological notion, as envisioned by a free-spirited person, that no day is predictable. Or let’s say that on any given day life can change.  The vocalist seems to understand, implicitly, that she’s currently going through a phase of unpredictability, one in which it appears intoxicants, both conventional and perhaps of the stronger type, are involved. And the ultimate goal in all of this is for her to truly ‘feel fine’. 

So going back to the beginning of it all, the initial assumption would be that the vocalist is unfulfilled or looking for something unspecified in life which set her out on this, shall we say unforeseeable path.

Release Date of “Everyday Is a Winding Road”

“Everyday Is a Winding Road” was released in November of 1996 as the 2nd single from the singer’s Grammy Award winning album, “Sheryl Crow”.

The song became the singer’s 4th single to top the charts in Canada. It peaked at number 12 in the UK, number 11 in the US and number 6 in Scotland.

Grammy Nomination

This song earned Sheryl a Grammy nomination in the “Record of the Year” category. However, Shawn Colvin’s “Sunny Came Home” beat it to win the prize. The following songs were also in contention for the said award:

• “I Believe I Can Fly” by R. Kelly
• “MMMBop” by Hanson
• “Where Have All the Cowboys Gone?” by Paula Cole

Popular Covers

Prince released his cover of the song in 1999 as part of his “Rave Un2 the Joy Fantastic” album. Another notable remake of the song is that of an a cappella group, Off the Beat which was released in 2000.

Who wrote “Everyday Is a Winding Road”?

Crow teamed up with American songwriters, Jeff Trott and Brian MacLeod in composing the song.

Crow’s “Sheryl Crow” Album

“Sheryl Crow” Crow’s self-titled album was released as her second studio album on September 24 of 1996. The singer holds production credits for the album which is largely regarded as her best album.

As part of the album’s promotion, five singles including “Everyday Is a Winding Road” were officially released from the album. The other singles include:

• “If It Makes You Happy”
• “Hard to Make a Stand”
• “A Change Would Do You Good”
• “Home”.

In 1999, it was included in a compilation of essential albums of the decade by Rolling Stone. About two decades later, the album appeared at number 475 on Rolling Stone’s “The 500 Greatest Albums of All Time” list in 2020.

The album peaked at very impressive positions on charts globally. Here is a list of how it performed in some parts of the world:

• US (6)
• New Zealand (6)
• Scotland (2)
• Switzerland (3)
• UK (5)
• Austria (8)

At the Grammy Awards in 1997, the album took home the award, “Best Rock Album”.