Wright moved to Nashville, Tennessee, following high school graduation and was cast in stage productions at the now-defunct Opryland USA amusement park.

[3][15] The summer of her final year in high school, she worked as a performing musician at the Ozark Jubilee, a long-running country music show in Branson, Missouri.

During the summer of 1990, she was re-hired as part of the Opryland cast for a second season and started taking classes at Middle Tennessee State University.

[3] The project spawned three singles ("He's a Good Ole Boy," "Till I Was Loved by You" and "Sea of Cowboy Hats") that all peaked outside the top 40 of the Billboard country chart.

Allmusic's Charlotte Dillon rated the project at four and a half stars, praising Wright's vocals and the album's mix of material.

She began working with a new manager (Clarence Spalding) and a publicist (Wes Vause), who helped secure her a contract with MCA Records Nashville.

Wright then contacted producer Tony Brown, who had previously made hit albums with Reba McEntire and Wynonna.

"[27] Meanwhile, Brian Wahlert of Country Standard Time gave it a less favorable response, finding some of the material to be fillers rather than quality music.

Once the recording was completed, producers Tony Brown, Buddy Cannon and Norro Wilson, believed the song could be a hit.

[21][33] Wright celebrated the number one on the road with fellow band members, Jay DeMarcus and Joe Don Rooney (both of whom would later form Rascal Flatts).

[35] One month later, MCA celebrated by throwing Wright a "Number One Party" where she invited numerous guests inside and outside the music industry.

"[39] Bill Friskics-Warren of The Washington Post noted that despite its country pop production, the record "hangs together as a sustained--and fairly compelling--song cycle about one woman's search for intimacy.

[54] Despite an intended album release, Wright exited Vivaton one month later, citing creative differences with label CEO, Jeff Huskins.

[56] She was inspired to write the song following a road-rage incident in which another driver was angry that Wright had a Marine Corps bumper sticker on her car.

[70] Lifted Off the Ground received four stars from Thom Jurek of Allmusic who cited Crowell's production and Wright's songwriting as the reasons for its success.

[66] Meanwhile, the Los Angeles Times believed Wright could have challenged the country music establishment more rather than "tread lighty" in her songwriting material.

[85] Critics have noted that Wright's MCA albums incorporated more contemporary styles, while also including the traditional country from her PolyGram days.

"[27] Stephen Thomas Erlewine observed a similar trend with 1999's Single White Female: "The record picks up where its predecessor left off, offering a selection of ten songs with clean, tasteful arrangements that place Wright in the forefront...Even when Wright and Brown shoot for the charts, they pull it off, since Chely never oversings and the instrumentation is never bombastic.

[84] In a similar vein, Stephen Thomas Erlewine found that she had not "completely abandoned the sound of contemporary country-pop", but also had "stripped-back and direct" songs.

[93] In the early 2000s, also joined wounded and recovering troops at a private military service event hosted by former vice president, Dick Cheney.

[118] In 2014, Wright spoke on the stage of the GLAAD Media Awards to discuss anti-bullying legislation with fellow activist Marcel Neergaard.

In 2016, Wright appeared on CNN encouraging the country music industry to be supportive of laws that protect transgender Americans in the state of Tennessee.

"[122] Wright helped inspire the creation of the 2022 book My Moment, which included stories from various female entertainers and their experiences with the MeToo movement.

[123][124] Wright harbored the belief her sexual orientation was immoral and that her secret would kill her career hopes, as a result of her Christian upbringing.

She stated that she wanted to come out to free herself from the burdens of living a lie, to lend support to LGBT youth, and to dismantle the notion that being gay is immoral.

lang came out in 1992 (though she later abandoned the country music genre), and Kristen Hall, formerly of Sugarland, was openly gay while working with that band.

[150][151] Following her announcement, Wright received support from fellow country artists LeAnn Rimes, Mary Chapin Carpenter, Faith Hill, Naomi Judd, SHeDAISY and Trisha Yearwood.

[153] Two weeks after publicly coming out, Wright met fellow LGBT activist and Sony Music marketing director Lauren Blitzer.

After having a series of migraine headaches that felt unusual, Wright went to the emergency room at New York's Lenox Hill Hospital.

Wright made the news public a year later to help encourage other people to seek medical attention if they notice similar symptoms.