Behind the Song: “Everyday is a Winding Road” by Sheryl Crow

Sheryl Crow had just released her debut, Tuesday Night Music Club, in 1993, then landed a tour with Crowded House on the Australian rockers’ Together Alone Tour, supporting their fourth album a year later. Throughout the course of the U.S. leg of the tour, Crow became good friends with the band, including Crowded frontman Neil Finn, who would end up singing backing vocals on “Everyday is a Winding Road,” which would later appear on her second album in 1996.

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The was initially written following the departure of Crowded House drummer Paul Hester, who had been going to therapy at the time, and was coping with severe depression for many years, before leaving the band in the middle of the tour, saying to Finn, “Every day is a winding road.”

Inspired by all the emotions surrounding Hester’s departure, Crow began to write on tour, penning most of the songs to her follow up self-titled album, including the hit “Everyday is a Winding Road.” 

Written by Crow, along with collaborators Jeff Trott and Brian MacLeod, the song, which was also featured in the John Travolta film Phenomenon in 1996, was about Hester’s personal struggles and the fact that every day is a gift, and a struggle at the same time. Years later, the song took on a whole new meaning for Crow, following Hester’s death, by suicide on March 26, 2005.

“Some songs resonate for me more powerfully than they did when they were written,” says Crow of the track. “And in some cases, they have taken on a new life form.”

These are the days when anything goesEveryday is a faded sign, I get a little bit closer to feeling fine, and He’s got a daughter he calls Easter, she was born on a Tuesday Night—Crow loosely referencing Hester’s daughter Sunday and her debut—“Everyday is a Winding Road” sounds upbeat on the surface, but its lyrics play out a whole other scenario.

“Having been around him and seeing someone really struggling and then ultimately taking his life… it still reflects now as we are further and further into this really hard, challenging time and caring about people suffering with the mental anguish of losing jobs,” says Crow on how the song also reflects on the hardships experienced during the pandemic.

“Songs like that are really a gift,” says Crow. “Songs like that seem to recreate themselves, and in a perfect world bring solace to some people.”

Several years following the death of Hester, Crow appeared on the British TV show Top of the Pops and shared more on the initial root of the song, and her friend.

”He inspired the song because he was so… he was such a character and so full of life, said Crow, “and it’s basically about the search for the meaning of life.”

Everybody gets high, everybody gets low
These are the days when anything goes
Everyday is a winding road
I get a little bit closer
Everyday is a faded sign
I get a little bit closer to feeling fine
He’s got a daughter he calls Easter
She was born on a Tuesday night
I’m just wondering why I feel so all alone
Why I’m a stranger in my own life
Jump in, let’s go
Lay back, enjoy the show

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