When she was a little girl, Chely would sit on her grandmother’s lap, put her hands over her grandmother’s, and the two would play piano together. Chely Wright was singing and playing professionally from as early as 11 years old, when the local American Legion branch hired her to play taps at veterans’ funerals. She continued to play for them throughout her high school years, until she graduated. During that time, she also performed at the Ozark Jubilee, a music show in Missouri. After she completed high school, Chely took a job at Opryland USA, located in Nashville, Tennesse.

Chely Wright signed with Mercury/Polgram in 1993 and released two albums on their label, neither of which were successful. As a result, Chely requested that they annul her contract and went on to sign with MCA Nashville instead. On the new label, Chely Wright produced her first successful album, titled Let Me in, which peaked at #25. The album contained her first hit single, Shut Up and Drive, which reached #14 on the Billboard Hot Country Singles and Tracks chart. Two other songs from the album, Just Another Heartache and I Already Do were released as singles as well.

In 1999, Single White Female was released on the MCA Nashville label as Chely’s fourth album. The album was certified gold and peaked at #15 on the Billboard Top Country Albums chart. It also contained Chely’s only single to every reach the top of the charts, the song which shared a name with the album. The music video for Single White Female was popular as well and was nominated for two awards. The next year, Chely Wright wrote a song together with Brad Paisley called Hard to Be a Husband, Hard to Be a Wife, which earned them a nomination for Vocal Event of the Year at the 35th CMA.

Chely Wright’s fifth album, Never Love You Enough, was supposed to come out on September 11, 2001, but after the WTC attack, the album was pushed off for two weeks. The album did not do as well as expected, peaking at #4 on the Country Albums chart. As a result, Chely Wright left MCA Nashville and signed instead with Vivaton, an independent label. The partnership was not a successful one and during her time with Vivaton Chely did not produce any albums. The next song from Chely Wright, Bumper of My SUV, was released on her own label through various radio stations and online.

In 2004, Chely released an EP on her own label, Painted Red Music Group. The album was originally only available though the website for Chely Wright fans, but later became available at major retailers such as Tartget, Wal Mart, and Best Buy. As a result of the EP’s success, Chely got a contract with Dualtone Records, which produced her sixth CD, The Metropolitan Hotel. In 2008, Chely once again switched labels, this time to Vanguard Records. On May 4, 2010, Lifted Off the Ground, Chely’s seventh album, was released and it later peaked at #32 on the Americana Music Charts.