Carolyn Kruse

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Massachusetts’ Jo Dee Messina has a role in Cole Swindell’s new video for his current hit single, “She Had Me at Heads Carolina. The song references the 1996 debut single, “Heads Carolina, Tails California,” from Holliston, Massachusetts’ hometown girl, Jo Dee Messina. She went on to become the most commercially successful country artist from New England. Cole’s song, along with a few other current singles, clearly shows there is a resurgence of love for 90s country music.

Cole Swindell released a new music video for his latest single. Pay attention to the bartender, when watching the video. Yup, that is our girl, Jo Dee Messina from Massachusetts, behind the bar, taking orders and serving drinks. When I chatted with Cole, after the release of his album, Sterotype, he talked about his love and appreciation of Jo Dee, her music, and Boston. You can listen to that conversation, below, as well as check out the new video from Cole. Also check out some of Jo Dee’s biggest hits, below. Roar on, 90’s country!

Jo Dee Messina fun fact:  The first time I spoke with Jo Dee was way back in the 90s. She had randomly called into the request line to tell me she was on her way to Nashville, from Holliston, to become a country music star. I chuckled, and said “of course you are,” and I wished her the best. But, I was thinking the odds were against her. I’m so happy I was completely wrong on this one! The next time we spoke, she told me the story of how when she first got to Nashville, she and Tim McGraw became friends. They told each other, whoever made it first in the biz, would help out the other. Tim made it first, getting signed to Curb records. A few years later, Jo Dee got signed to the same record label. Tim co-produced her debut album. He held true to their pact, and the rest is country music history!

Get the whole story on Jo Dee’s debut single below!

  • Watch the Video for Cole Swindell's "She Had Me At Heads Carolina"

  • My Interview With Cole Swindell

    A few months ago, I chatted with Cole Swindell about his song “She Had Me At Heads Carolina,” and it wasn’t even released yet. We talk about his love of 90s country, Jo Dee Messina, Boston, and his album Stereotype. You can listen HERE. 

    Cole Swindell and Carolyn Kruse

  • Watch Jo Dee Messina's "Heads Carolina, Tails California" from 1996

    Jo Dee’s debut release was quite impressive, for an artist not from the south! In fact, it went all the way up the charts to #2 in 1996, from her self-titled debut album.

  • Watch Jo Dee Messina's Video from Her First #1 Hit

    Messina’s first #1 came in 1998 with the release of her sophmore album, I’m Alright. “Bye, Bye” was written by Phil Vassar (“Just Another Day In Paradise), who also wrote the title trace. This would be the first of 3 consective #1 hits for Jo Dee, all from this same album.

  • The Story Behind "Heads Carolina, Tails California" from Jo Dee Messina

    Jo Dee shares the complete story of how “Heads Carolina” came to be her debut single, and why she changed some of the lyrics. Here’s a fun fact Jo Dee once told me: When first meeting with record labels, Jo Dee would tell them they needed a red head, most responded with, “country music has a red head, Reba McEntire.” Btw, you know Jo Dee had the opening lyrics changted “Heads Carolina, Tails California” to include, “I got people in Boston.”