Chely Wright may be one of the most underrated country music artists to emerge from the genre's 90s heyday. For many, she is known for her No. 1 hit, "Single White Female," but Wright's discography — and career — is much richer than just one song.

Born Oct. 25, 1970, in Kansas City, Mo., Wright was raised in Kansas and moved to Nashville, Tenn., after graduating high school. She performed in stage productions for the now-closed Opryland USA amusement park until she scored her first record deal. She released two albums that earned praise from critics, but neither cracked the mainstream.

After parting ways with Mercury Records, Wright inked a deal with MCA Records Nashville and enlisted producer Tony Brown to work on her next LP. The result was 1997's Let Me In, which spawned her Top 40 radio hit, "Shut Up and Drive."

Wright joined forces with Brown once again for her 1999 LP Single White Female, and its title track became the country talent's first career No. 1. While her career reached new highs, Wright was also struggling with hiding her sexual identity.

In 2010, Wright made history by coming out via a raw and revealing feature in People Magazine, just one day before releasing her memoir, Like Me: Confessions from a Heartland Country Singer. For Wright, writing the book was about liberating herself from a lie and offering support to others who struggled in the same ways. 

A lifelong activist for education and veterans, Wright now dedicates much of her time to supporting causes within the LGBTQIA+ community, including efforts through her own non-profit organization, LIKEME.

Her two most recent albums — 2010's Lifted Off the Ground and 2016's I Am the Rain — sparkled with personal tracks steeped in the Americana tradition. While Wright's recent work has yet to reach the commercial success of her past, her artistry has only continued to grow.

Let's take a look back at 10 of Chely Wright's best songs so far.

  • 10

    "What About Your Heart"

    from 'I Am the Rain' (2016)

    In 2016, Wright released her long-awaited album, I Am the Rain, which was funded by Wright's fans through a 2014 Kickstarter campaign. The resulting songs were some of Wright's most personal ones yet and some of her most definitively Americana-sounding tracks to date. The standout cut, "What About Your Heart," is a soft, acoustic track that asks a big question: "You feel bad because you know that you need more / Baby, what about your heart?"

  • 9

    "I'm Trying" (with Diamond Rio)

    from 'One More Day' (2001)

    In 2001, Wright joined Diamond Rio on their seminal album One More Day for a heart-rendering ballad. "I'm Trying" tells the story of a couple who strives to be strong together in the face of one partner's all-too-threatening vices.

    Wright delivers one of the tune's most emotive lines, singing, "I don't want to think you're lying / And though I haven't found the faith that I need / I'm trying."

  • 8

    "Sea of Cowboy Hats"

    from 'Woman In the Moon' (1994)

    While Wright's debut album didn't make the commercial splash she had hoped, that wasn't for lack of genuinely great, bona fide country songs. "Sea of Cowboy Hats" possesses a distinct honky-tonk swagger bound to get you two-stepping.

  • 7

    "Jezebel"

    from 'Never Love You Enough' (2001)

    On "Jezebel," Wright doesn't kindly plead with the Jolene in her life. Over a pop-country beat, she sings, "Jezebel, save your charms / He'll be back here in my arms / Oh how quickly you forget he's not yours yet." 

    Written by Rascal Flatts' Jay DeMarcus and Marcus Hummon, the track was included on her 2001 album, Never Love You Enough, and broke into the Top 30 of Billboard's Hot Country Songs chart. 

  • 6

    "Feelin' Single and Seein' Double"

    from 'Let Me In' (1997)

    Initially recorded by George Jones and later by Emmylou Harris, "Feelin' Single and Seein' Double" is a classic country tune about hitting the bars and winding up in trouble back home. Wright's recording puts her with the best of them.

  • 5

    "She Went Out for Cigarettes"

    from 'Single White Female' (1999)

    "She Went Out for Cigarettes" is a classic story song of domestic disappointment, written by Jon McElroy and Ronnie Guilbeau. With devastating calm and poise in her voice, Wright delivers the tale of our unappreciated heroine and her eventual liberation.

  • 4

    "It Was"

    from 'Single White Female' (1999)

    A charming ode to love, "It Was" is another stellar cut from Wright's 1999 album Single White Female. Penned by Gary Burr and Mark Wright (no relation), the captivating tune climbed to No. 11 on Billboard's Hot Country Songs chart.

  • 3

    "He's a Good Ole Boy"

    from 'Woman In The Moon' (1994)

    In retrospect, it's a genuine puzzle as to why Wright's "He's a Good Ole Boy" never ascended to the top of the charts. Musically, the track is in peak 90s country form: Wright's natural twang soars over jaunty fiddles and steel guitar. What makes it truly special, however, is the song's humor. 

    Wright deadpans: "To steal him's been your number one ambition / But sister, here's one safe that you don't have to crack / I'll hand him over under one condition / A deal's a deal and you can't give him back."

  • 2

    "Shut Up and Drive"

    from 'Let Me In' (1997)

    Let Me In was Wright's first album to chart on the Billboard 200 and supplied her earliest country radio hit. "Shut Up and Drive" is an empowering song about a woman who finally listens to her voice after ignoring it for far too long.

  • 1

    "Single White Female"

    from 'Single White Female' (1999)

    In 1999, Wright landed her first and only No. 1 hit with "Single White Female," which tells the story of a woman who makes her romantic feelings known in the classified ads. Wright's vocals are bold and playful on the track, which Carolyn Dawn Johnson wrote with Shaye Smith, and features harmonies from Trisha Yearwood.

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