Born 56 Years Ago Today in Massachusetts, the Tim McGraw Protégé With Six No. 1 Hits and a Place in Country Music History

Releasing her self-titled debut album in 1996, Jo Dee Messina came in hot with infectiously relatable hits like “I’m Alright” (1998) and “That’s the Way” (2000). Part of a late ’90s-early aughts crop of female crossover country stars, Messina released nine consecutive top 10 hits between 1998 and 2001. She was also the first female country artist to score three multi-week number-one songs from the same album.

Jo Dee Marie Messina was born in Framingham, Massachusetts, on this day (August 25) in 1970. In honor of her 56th birthday, we’re taking a look at her remarkable career.

How This Hall of Famer Helped Jo Dee Messina Get Her Start

Inspired by other trailblazing female country artists like Reba McEntire, Patsy Cline, and the Judds, Jo Dee Messina was singing in local clubs at age 16 — backed up by her brother and sister on drums and guitar.

At 19, she moved to Nashville hoping to kick-start her country music career. There, Messina worked various jobs while entering talent contests around Music City.

One win led to a regular gig on the radio show Live at Libby’s, where she caught the attention of producer Byron Gallimore. He helped the aspiring singer assemble a demo tape.

Gallimore also worked with Grammy-winning superstar Tim McGraw, whom Messina met and befriended.

Backstage at one of his concerts, she met an executive from the “Don’t Take the Girl” crooner’s label, Curb Records. Jokingly, Messina suggested they needed a redhead.

But producer James Stroud, who had just heard her demo tape, stepped up to vouch for the artist. Soon, she had signed a contract with Curb Records, where Gallimore and McGraw would co-produce all her albums.

She Fought for Her Career

Released in March 1996, Jo Dee Messina’s self-titled debut album spawned two top 10 hits in “Heads Carolina, Tails California” and “You’re Not in Kansas Anymore”.

Her career on fire, Messina would play 215 shows in 1996. However, touring and employee expenses ended up leaving her $500,000 in debt.

As she was preparing to release her sophomore album, I’m Alright, in late 1997, Messina’s management team encouraged her to file for bankruptcy.

“I said, ‘That’s like giving up. Let’s wait until after the holidays, because Music Row shuts down for the holidays,’” she told Nashville Scene in 2001. “Let’s wait and see what happens.’”

By August 1998, Messina had landed two number-one hits in “Bye Bye” and the album’s title track, “I’m Alright”. She followed up with another chart-topper, “Stand Beside Me”.

The album’s final two singles, “Lesson in Leavin’” and “Because You Love Me”, peaked at number two and number eight on Billboard’s Hot Country Songs chart, respectively. (And for what it’s worth, she paid off her debts in summer 2000.)

A Crossover Success

Jo Dee Messina’s hot streak (no pun intended) continued with her third album, 2000’s Burn.

The album yielded two additional number-one hits, “Burn” and the Tim McGraw duet “Bring on the Rain”.

[RELATED: Jo Dee Messina Reflects on 30 Years of “Head Carolina, Tails California” and Delves Into Her New Album (Exclusive)]

After taking a break to grapple with alcohol addiction, Messina released her number-one album A Delicious Surprise in 2005. The lead single, “My Give a Damn’s Busted” — co-written by Joe Diffie — gave the CMA Award-winning artist her final career number-one hit.

Nearly three decades later, it isn’t over for Jo Dee Messina. In June 2026, the two-time Grammy released her seventh album, Bridges — marking her first full-length album since 2014’s Me.

Featured image by Taylor Hill/FilmMagic