With her self-titled 1996 debut album, Jo Dee Messina added a huge dose of talent, wit and honesty to country radio. The Massachusetts-born artist moved to Nashville at the age of 19 and befriended Tim McGraw, who Messina credits with helping to launch her recording career. After Curb records only agreed to record a handful of tracks, McGraw, who was signed to the label at the time, stepped up.
"McGraw, at that time, said, 'She deserves a whole album, not just three or four sides,'" Messina told I Miss...90s Country Radio with Nick Hoffman (quote via CMT). "I'll pay for it. If you like it, then you can reimburse me."
However, as Messina's songs would prove, it was her own immense talent and tenacity that would make her own of '90s country's most beloved stars — a fact made even more apparent by Cole Swindell's recent nod to Messina's signature song in "She Had Me at Heads Carolina."
From a perseverant anthem to a tune about a couple with no limits on their future, here are our picks for the 12 best Jo Dee Messina songs.
"You're Not in Kansas Anymore"
On "You're Not in Kansas Anymore," Messina shares a relatable story of a small town boy who moves to the big city and finds love with a California girl.
"Lesson in Leavin'"
A recording of one of Dottie West's greatest hits, Messina made the timeless kiss-off "Lesson in Leavin'" her own when she recorded it for her album I'm Alright.
"Dare to Dream"
Much like "Heads Carolina, Tails California," "Dare to Dream" celebrates a couple with nothing but forever in front of them.
"I'm Alright"
Written by fellow country music artist Phil Vassar, "I'm Alright" became Messina's second consecutive No. 1 single on Billboard's Hot Country Songs chart. The song's message of perseverance through the hard times resonated with listeners and Messina was the perfect artist to deliver the rallying cry.
"My Give A Damn's Busted"
This song about a woman fed up with codependent partner hit No. 1 on the country charts in 2005 and provided the perfect response for anyone dealing with an emotionally manipulative ex. It's a Joe Diffie co-write from Messina's Delicious Surprise album.
"Bring On The Rain"
Featuring backup vocals by none other that Messina's friend Tim McGraw, "Bring on the Rain" is a gorgeous song of comfort for anyone going through trying times. It's one of two Messina songs (along with That's the Way") to earn a Grammy nomination.
"That's The Way"
Written by Annie Roboff and Holly Lamar, "That's the Way" lays out life's hard truths along with an empowering message to keep going.
"Because You Love Me"
Written by Kostas and John Scott Sherrill, this ballad about the healing power of love went to the top 10 on the country charts in 1999.
"Burn"
The title track to Messina's 2000 album, "Burn" is a message to live life to the fullest and with passion.
"Stand Beside Me"
There are plenty of country songs about women standing by their men. Messina asks the same in return in "Stand Beside Me," the third single from her album I'm Alright.
"Bye Bye"
In 1998, Messina delivered the perfect kiss-off to a no-good boyfriend with "Bye Bye," her first No. 1 single.
"Heads Carolina, Tails California"
This infectious tune about a young couple who use a quarter to decide their future served as Messina's debut single and helped make her one of the most beloved vocalists of the '90s.
Honorable Mentions: 'Downtime," 'I Wish," "It's Too Late to Worry," "Do You Wanna Make Something of It," "Was That My Life," These are the Days," "A Woman's Rant," He'd Never Seen Julie Cry"
This story originally ran on Sept. 20, 2018. It was updated on Aug. 25, 2022.
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