100 Greatest Women, #62: Jo Dee Messina

100 Greatest Women: 10th Anniversary Edition


Jo Dee Messina

2008 Edition: #53 (-9)

One of the few major country stars to hail from the northeast, Jo Dee Messina is a Massachusetts native who moved to Nashville when she was nineteen.

While doing office jobs during the day, she performed in talent shows and on the radio show Live at Libby’s. Producer Byron Gallimore heard her on the radio show and contacted her. They agreed to work together to secure her a record contract, and Messina became fast friends with another young hopeful, Tim McGraw. When McGraw broke through, he introduced Messina to his label executives at Curb. They signed Messina, and McGraw and Gallimore came on board as her producers.

Messina launched the year after Shania Twain broke through with The Woman in Me, and the market was ripe for strong female artists who knew their way around a country-pop hook. Messina’s first single, “Heads Carolina, Tails California”, went straight to No. 2, and the follow-up “You’re Not in Kansas Anymore” also went top ten.

Messina was off to a good start, but when the next two singles stalled, her momentum slowed down. Some unlucky business choices made the next year difficult, but when she resurfaced in early 1998, her career exploded. A pair of singles written by rising songwriter Phil Vassar spent multiple weeks at No. 1, and “Bye-Bye” and “I’m Alright” were included on a CD single that went gold. Her sophomore album, I’m Alright, sold strongly.

The industry embraced Messina, and as she scored two more big hits with “Stand Beside Me” and “Lesson in Leavin’,” she won both ACM Top New Female Vocalist and the CMA Horizon Award in 1999. She finished the year as the most-played female act on country radio.

In 2000, she released her third album, Burn. It entered at #1 on the country album chart, and lead single “That’s the Way” was a four-week #1 hit. The title track and “Downtime” were also big hits. The label didn’t want to release the album closer, “Bring on the Rain”, as a single, but Messina pushed hard. The resilient song became a post-9/11 anthem, and helped push the album to platinum.

After that, however, Messina received more resistance from her label. It rejected her fourth studio album, and dismantled it by tacking a handful of its cuts on to a Greatest Hits album in 2003. Even the label must have been surprised when that hits collection entered at No. 1, and it went on to sell gold, with a little help from the top thirty hits “Was That My Life” and “I Wish.”

Two years later, Messina made a big comeback at country radio with “My Give a Damn’s Busted,” a Joe Diffie-penned track that had been recorded by him first, but that his label had refused to release as a single. It rocketed to #1, as did her first studio album in five years, Delicious Surprise. Even though the next three singles from the project weren’t embraced by radio, the album was certified gold.

Messina’s label repeatedly pushed back her next studio album, until it was released as a trilogy of digital EPs in 2010.  She finished her long tenure at Curb Records in 2012, and moved on to the independent music scene. Her 2014 release for Dreambound Records, Me, hit the country top twenty in 2014.

In the years since, she began writing songs for an inspirational project. Sadly, she was required to suspend all public appearances in fall 2017 as she entered treatment for cancer.  But in 2018, she returned to the road, along with a single, “Bigger Than This,” which was released digitally to all major music outlets.

Essential Singles

  • Heads Carolina, Tails California, 1996
  • Bye Bye, 1998
  • I’m Alright, 1998
  • Bring On the Rain (with Tim McGraw), 2001
  • My Give a Damn’s Busted, 2005

Essential Albums

  • I’m Alright (1998)
  • Burn (2000)
  • Delicious Surprise (2005)

Industry Awards

  • Academy of Country Music
    • Top New Female Vocalist, 1999
  • Country Music Association
    • Horizon Award, 1999

100 Greatest Women: 10th Anniversary Edition

Next: #61. Juice Newton

Previous: #63. Felice Bryant


  1. I played the greatest hits album to death when it came out. Definitely someone who you could see the immediate impact Shania had on the format. The essential singles are my favorites.

    I’ve seen her twice on tour in the last few years. Nothing really excited me on the last album but Will You Love Me now is great. Really can feel her emotion on it.

  2. I still think of “Heads Carolina, Tails California” (Tim Nichols and Mark D. Sanders) as a song that should be played as you drive down a highway in a convertible with the top down and the wind whipping through your hair. I say this even though I have never been in a convertible and have no desire to own one (and I don’t have much hair for the wind to whip through anymore). That image pops into my mind whenever I hear HCTC and Bye Bye, just as it did the first time I heard “Long Train Running” by the Doobie Brothers.

    “Delicious Surprise” was a very pleasant surprise, from the opening track “Not Going Down” to the powerful 12th track “You Were Just Here” which was not released as a single. Loved the sassy “My Give A Damn’s Busted”. The title track was actually one of my least favorite songs.

    I didn’t know that Curb records gave her such a hard time.

  3. Jo Dee Messina is an artist where the songs of hers that I love are hits. But boy if she releases a song I don’t care for it does awful, most egregious example being “Biker Chick”.

    It’s a shame she was on Curb because on a better label, I think Jo Dee Messina could’ve had a bit more of an impact.

  4. Love me some Jo Dee Messina. She is one of the best female artist from arguably the most diverse era in women’s country music, the 90’s. I’m Alright, Bye, Bye, Heads Carolina, Tails California, and Bring On The Rain are classic tracks.

  5. That’s a question I’m sure LeAnn Rimes, Tim McGraw, and especially Hank III would love to have answered, because that’s about par for Curb Records, which has a reputation for sandbagging the careers of its artists.

  6. Jo Dee is timeless. The mark of a true artist is when you hear the first three to four words fall from their lips and you INSTANTLY know who the artist singing is. Jo Dee has that caliber of talent and identity. Sad to see her talent not capitalized on. Curb did her the similar way RCA never truly promoted Sara Evans.

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