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This hit song from the 90s has a deeper meaning to help get you through tough times.

In 1996, CD players became more mainstream, Independence Day swept box offices, and sitcoms like Seinfeld and Friends permeated pop culture.

While the rest of the country snacked away on blue M&Ms and Lunchables, legendary singer-songwriter Sheryl Crow casually dropped her self-titled album, featuring her now iconic song “Everyday Is a Winding Road” as the second track.

The song quickly became a top performer, peaking at #11 on the Billboard Hot 100 that year and earning a #4 spot on the US Top 40 chart. It also became known as a favorite track of the late Prince.

But while the song is upbeat and cheery, the deeper meaning behind “Everyday is a Winding Road” tells a personal story of resiliency Crow felt compelled to share with listeners.

Sheryl Crow’s Road to Success

Sheryl Crow and Michael Jackson perform during the "BAD" Tour
(Getty)

As a musical artist, Crow came from humble beginnings, teaching music during the day at an elementary school in the late 80s. She used her weekends to sing in a local band in Fenton, Missouri, which led her to meet record producer Jay Oliver. This partnership led Crow to land vocal spots on a few national commercials. From there, Crow worked as a background vocalist on tour with Michael Jackson, which led her to record for other popular artists at the time, including Jimmy Buffet, Stevie Wonder and Belinda Carlisle.

After these initial successes, Crow decided it was time to start working on an album of her own. However, Crow and her producer were ultimately unsatisfied with the result and did not release it publicly.

Undeterred, Crow began working with Tuesday Music Club, a collective of musicians she was introduced to through her relationship with musician Kevin Gilbert. Crow worked with the group to create her first album, Tuesday Night Music Club, which included her first hit, “All I Wanna Do.”

The album sold over 7 million copies in the US and UK throughout the 1990s. The album was given a Grammy Award for Record of The Year. Crow also took home Best New Artist and Best Female Vocal Performance that year at the Grammys, which helped pave the way for the success of “Everyday Is a Winding Road.”

The Story Behind “Everyday Is a Winding Road”

Sheryl Crow in Concert at Irving Plaza - 1993
(Getty)

After the release of her debut album, Crow joined the “Together Alone Tour” with headliners Crowded House, an Australian rock band. Crow formed close relationships with the band members during the tour, including drummer Paul Hester. Hester had been battling depression, for which he received therapy during the tour. Unfortunately, Hester reached a point during the tour where he felt he could not continue due to depression and needed to take a break. Reportedly, Hester’s parting words to the band’s frontman were, “Every day is a winding road.”

Observing Hester’s battle with depression on tour inspired Crow to write the song “Everyday is a Winding Road,” reflecting on how life can feel like a burden and a blessing within the span of a day. The song was featured in the 1996 film Phenomenon starring John Travolta.

The song’s music video reflects the song’s upbeat tone, showing Crow playing at a playground with other children.

Stand-out scenes include Crow swinging on a swing and sliding down slides, signifying the ups and downs of life that are alluded to within the song. Reflection is also a popular motif in the music video, showing Crow wearing reflective glasses and mirrors that passersby look into on the street.

The death of Paul Hester

Hester died by suicide in March of 2005, which is when Crow began to speak more deeply about the song’s meaning. “Some songs resonate for me more powerfully than they did when they were written,” said Crow in an interview. “And in some cases, they have taken on a new life form.”

Following Hester’s death, Crow appeared on Top of Pops, a British TV show, to speak more about how Hester inspired the song. “He inspired the song because he was such a character and so full of life,” said Crow, noting that the song is basically about the search for the meaning of life.

Analyzing “Everyday is a Winding Road”

Sheryl Crow in Torhout/Werchter Festival, Torhout, Belgium, 5th July 1997.
(Getty)

Crow has explained much of the meaning behind the song, including the below nod to Hester’s daughter, Sunday.

“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”

The celebration of having a daughter juxtaposed with feeling alone in life, like a stranger who isn’t truly connected to anyone despite being a father, is gut-punching. Setting lyrics like this to an upbeat track signifies the resilience of continuing on even when you’re feeling low. In fact, the phrase, “Everybody gets high, everybody gets low,” is repeated throughout the song, as if trying to write this sadness off as something everyone goes through.

Though the song was based on Hester’s mental health struggle, Crow said songs like this one are a gift in that they can recreate themselves to bring solace to others during difficult times. She hoped listeners would take that message away from this song when listening to it during the pandemic:

“Having been around [Hester] 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.”

Sheryl Crow’s “Everyday is a Winding Road” Full Lyrics

Sheryl Crow at the Pacific Club, Antwerp, Belgium, 28th January 1994.
(Getty)

What deeper meaning do you find in Crow’s words? Here are the full lyrics to her hit 1996 song.

“I hitched a ride with a vending machine repair man
He says he’s been down this road more than twice
He was high on intellectualism
I’ve never been there but the brochure looks nice

Jump in, let’s go
Lay back, enjoy the show
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
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

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

I’ve been swimming in a sea of anarchy
I’ve been living on coffee and nicotine
I’ve been wondering if all the things I’ve seen
Were ever real, were ever really happening

Everyday is a winding road
I get a little bit closer
Everyday is a faded sign
I get a little bit closer

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”

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