She drew influence from a variety of country music artists, including Patsy Cline, Reba McEntire, and The Judds.

By age 16, she was playing local clubs, singing while her brother and sister provided backup on drums and guitar.

Realizing that living in the Northeast would limit her chances of achieving country music stardom, Messina moved to Nashville, Tennessee, at age 19.

She worked various temporary jobs, including computer programming and accounting, while entering talent contests around Nashville.

One win led to a regular gig on the radio show Live at Libby's, which caught the interest of producer Byron Gallimore, who helped her assemble a demonstration tape.

Backstage at one of his concerts, McGraw met an executive from his label, Curb Records, and jokingly suggested that they needed a redhead.

It spawned two top-10 hits, starting with the lead single, "Heads Carolina, Tails California", which peaked at number two on the country charts and its follow-up, "You're Not in Kansas Anymore" gained similar success.

[2] However, the two additional singles released from the album, "Do You Wanna Make Something of It" and "He'd Never Seen Julie Cry" peaked outside the country top 40 and were minor hits between 1996 and 1997.

Messina's finances suffered due to a series of poor business decisions and a change of management that led her to nearly declaring bankruptcy; she nearly lost her home and her car.

[7] The lead single, "My Give a Damn's Busted" (co-written by country music star Joe Diffie), peaked at number one on the Billboard Country Chart and became Messina's first number-one single since “Bring On the Rain” in 2002, and her last number one hit of her career.

The three follow-up singles - "Delicious Surprise (I Believe It)" "Not Going Down," and "It's Too Late To Worry" - were minor top-40 hits on the Billboard country chart between 2005 and 2006.

[citation needed] Messina released a new single in July 2007, "Biker Chick", from her fifth studio album, Unmistakable.

[8] Although the album was set for release on November 6, 2007, it was shelved, and the single was dropped from country radio after spending 9 weeks on the charts, rising to a peak of number 48.

"[13] Having had her first child in January 2009,[14] Messina was inspired to write the song while spending time with her son on a trip to Jasper, Alberta in Canada, where she saw mountains with glacier lakes.

The single received a negative review at Engine 145, where critic Sam Gadzidak thought that it was derivative of Lee Ann Womack's "There Is a God".

[citation needed] In 2011, Messina signed to promote the WD-40 line of cleaners with a campaign called "Unmistakably Clean".

A collection of her songs is available for free download with the purchase of specially marked Spot Shot, Carpet Fresh, 2000 Flushes, or X-14.

[16] In 2012, Messina was featured on the fourth season of Bravo's hit reality show The Real Housewives of Atlanta.

[17] While Messina anticipated that they would be a part of a new EP, entitled Masquerade, she has since reassessed the direction of her music and is continuing to write new material, mostly faith-based in an effort to share God's word, for an eventual project.

[20] To follow up her faith-based, original song, Messina released her own version of Cory Asbury's award-winning "Reckless Love" to country and Christian radio.