Sheryl Crow and Willie Nelson during "Willie Nelson and Friends: Live and Kickin'" Premieres on USA Network May 26, 2003 - Show at Beacon Theatre in New York City, New York, United States.
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Sheryl Crow's 10 Best Country Songs and Collaborations

The life and career of legendary singer-songwriter Sheryl Crow is spotlighted in the new documentary Sheryl, which premieres on Showtime on May 6. The documentary, a long overdue celebration of a true rock icon, will trace Crow's musical journey, from a dreamer growing up in small town Missouri to her breakout album Tuesday Night Music Club and beyond. It will also chronicle the "high highs and low lows" of her life and career. The official trailer for the film, which debuted at SXSW earlier this year, shows Crow discussing her battle with cancer.

Like so many great artists, Crow has transcended genres throughout her her incredible career. It's not a stretch to think that if "Strong Enough" or "All I Wanna Do" were released today, they'd be labeled as "Americana" and played on your local indie country stations (or added to Spotify's Indigo playlist).

In a 2013 interview with the Hollywood Reporter, Crow said she looks to Emmylou Harris and Willie Nelson as the blueprint for artists who've blazed their own trail, calling them the "matriarch and patriarch of the format."

"They've written songs that have been in every format," Crow said. "That's what I'm much more interested in than proving myself to a radio programmer. I want to write songs that resonate with people, and the songs I care about most will never be heard at radio anyway. That's the way it's always been, on all of my records. There have been songs I felt were so important that never got played, and people that are fans know those songs."

In the nearly 30 years since the release of her debut album, Crow has collaborated with Nelson and Harris, as well as Kris Kristofferson, Vince Gill, Maren Morris, The Highwomen, The Chicks, Chris Stapleton and more.

Take a look back at Sheryl Crow's best country moments.

"Waterproof Mascara"

Co-written by Crow, Brad Paisely and Chris Dubois, "Waterproof Mascara" is the type of country gold that would make Tammy Wynette proud.

"Nobody's Perfect," Emmylou Harris

One of many stunning collaborations from Threads, Crow and Emmylou Harris' "Nobody's Perfect" is a perfect showcase for two legendary vocalists.

"Everything Is Broken" with Jason Isbell

Another stunner from Threads, "Everything is Broken" finds Crow teaming up with another country-rock troubadour, Jason Isbell.

"Prove You Wrong" with Stevie Nicks and Maren Morris

Three generations of incredible singer-songwriters, Crow, Maren Morris and Stevie Nicks, collaborate on the defiant "Prove You  Wrong."

"Lonely Alone," featuring Willie Nelson

One of Crow's many duets with the great Willie Nelson, "Lonely Alone" was featured on Crow's duets album Threads.

"I wrote the song, 'Lonely Alone,' with Willie in mind," Crow said in a statement. "It's was written as kind of a barside cowboy noir with romantic Spanish inflections, but the song has taken on new meaning during these times. I hope people find the same comfort in this song that I have always found in Willie. I never feel closer to home than when I am singing with him — I know a lot of people feel the same way, even if they're just singing along with him on the radio. I felt that this was the perfect song and the perfect sentiment to celebrate Threads with."

"Coal Miner's Daughter" with Loretta Lynn and Miranda Lambert

In 2010, Crow recorded Loretta Lynn's autobiographical tune with Miranda Lambert and the Coal Miner's Daughter herself.

"Tell Me When It's Over" with Chris Stapleton

Chris Stapleton joined Crow for the bluesy groover "Tell Me When It's Over."

"Strong Enough"

A track from Crow's iconic debut Tuesday Night Music Club, "Strong Enough" is simply one of the best country songs of the '90s...that never hit the country charts.

Nothing's true and nothing's right/ So let me be alone tonight," Crow sings. "'Cause you can't change the way I am/ Are you strong enough to be my man?/ Lie to me/ I promise I'll believe/ Lie to me/ But please don't leave."

That pedal steel is enough to break your heart.

"Heaven is a Honkytonk" with The Highwomen

A match made in heaven, Crow collaborated with country supergroup The Highwomen for "Heaven is a Honkytonk."

"You Were Mine" with The Chicks

Crow and The Chicks have collaborated several times throughout their careers — the trio even joined Crow onstage at Lilith Fair and for a performance on "Strong Enough" at Central Park, but it doesn't get better than their performance of Wide Open Spaces standout "You Were Mine." Crow called it "one of the best songs ever written."

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