10 Best Jo Dee Messina Songs

Let’s face it. The late ‘90s and early 2000s wouldn’t have been the same without Jo Dee Messina. The Framingham, Massachusetts native brought a strong female voice to the country genre with her musical talent, high-energy performances, and spunky personality.

But, Messina’s songs showcased her ability to deliver a range of emotions vocally. So much so that she became the first female country artist to score three multiple-week No. 1 songs from the same album. With tracks like “Bring On The Rain,” “Stand Beside Me,” and “Lesson In Leavin,’” Messina’s catalog covered an entire decade of hits.

Here are 10 unforgettable songs by Jo Dee Messina.

10. “Because You Love Me” 

Written by Kostas, John Scott Sherrill (1999) 

“Because You Love Me” marked the final single from Messina’s I’m Alright album, which also featured the title track, “Bye, Bye,” “Stand Beside Me,” and a cover of Dottie West’s “Lesson in Leavin.’” “Because You Love Me” was met with favorable reviews thanks to Messina’s honest articulation of the tune’s sentimental lyrics. The power ballad didn’t reach No. 1 on the charts, but it did become a crossover success for Messina, peaking at No. 53 on the Billboard Hot 100 chart.

9. “Burn” 

Written by Tina Arena, Pam Reswick, Steve Werfel (2000) 

The title track from her album of the same name, “Burn,” has Messina sharing the message to follow your dreams while asking the listener questions like “Do you wanna be a poet and write?” and “Do you wanna be an actor up in lights?” Messina wasn’t the first artist to record “Burn” for her album. By the time she got her hands on the tune, it was already a hit, originally co-written and recorded by Australian singer Tina Arena. But, it’s a good thing Messina cut it, as her version took the No. 2 spot on the Billboard Hot Country Songs chart.

8. “My Give A Damn’s Busted” 

Written by Joe Diffie, Tom Shapiro, Tony Martin (2005) 

Messina gets feisty in the straightforward, over and done with it anthem “My Give A Damn’s Busted.” Just like “Burn,” though, she wasn’t the first artist to cover the tune. The late Joe Diffie, who co-wrote the track, previously recorded the song for his 2001 album, In Another World. Finding its way onto Messina’s Delicious Surprise album in 2005, the tune spent two weeks atop the Billboard Hot Country Songs chart.

7. “Stand Beside Me” 

Written by Stephen Allen Davis (1998) 

Messina navigates romantic relationships and also shares what she’s looking for in a man in her catchy track, “Stand Beside Me.” Featured on her breakthrough album, I’m Alright, “Stand Beside Me” gave Messina her third overall hit from the project. The song held the top spot on Billboard‘s Hot Country Songs chart for three weeks.

6. “That’s The Way”  

Written by Annie Roboff, Holly Lamar (2000) 

Messina rolled into the year 2000 with a roll with the punches kind of attitude, as heard on her upbeat track, “That’s The Way.” The tune, co-written by Annie Roboff and Holly Lamar, has the Massachusetts native telling folks that getting back up after getting knocked down is all a part of life. “That’s The Way” is the lead-off single from Burn – Messina’s first studio album to go No. 1 on the Billboard Country Albums chart. The tune also found massive success, peaking at No. 25 on Billboard’s Hot 100 Chart and spending four weeks at the top of the Billboard Hot Country Songs Charts.

5. “Bring On The Rain” w/ Tim McGraw 

Written by Billy Montana, Helen Darling (2001) 

In 2001, Messina teamed with fellow country superstar Tim McGraw on the empowering collaboration “Bring On The Rain.” The pop-country ballad and fourth single from her Burn album showcased Messina’s soft side in comparison to spunky tracks like “My Give A Damn’s Busted” and “Lesson In Leavin’.” The hitmaker’s earnest vocals paired with McGraw’s signature twang harmonies made for a flawless duet. It’s no wonder why the touching acoustic track, co-produced by McGraw, became a No. 1 country hit!

4. “Lesson in Leavin’” 

Written by Randy Goodrum, Brent Maher (1999)

You’d be hard-pressed to find another tongue-twister sing-along catchier than “Lesson In Leavin’” in the ’90s. But it may come as a surprise to find out that the song had already been a hit long before Messina tackled it. In 1979, the late Dottie West recorded the goodbye tune (then titled “A Lesson In Leavin’”) for her Special Delivery album and took the song to the top of the charts. Messina’s re-titled version of the track, recorded as a tribute to West, also nabbed the top spot on Billboard’s Hot Country Songs chart, becoming her fourth hit on the album, I’m Alright.

3. “I’m Alright” 

Written by Phil Vassar (1998)

In 1998, Messina put a female spin on “I’m Alright” and took the sunny tune to the top of the Billboard Country Songs chart for three straight weeks. Written by fellow country artist Phil Vassar, “I’m Alright” also appeared on Vassar’s 2006 Greatest Hits, Vol. 1 album. Messina’s version is featured on her album of the same name, which is also her highest selling album to date.

2. “Bye, Bye” 

Written by Phil Vassar, Rory Bourke  (1998)

Messina shows off her spunky attitude as she tells a potential love interest that she has run out of patience to wait around for him any longer in the infectious upbeat track, “Bye Bye.” The lead single from her I’m Alright album, “Bye, Bye,” became Messina’s first hit, topping both the U.S. and Canadian country charts. Like “I’m Alright,” “Bye, Bye,” co-written by Vasser, also appears on his Greatest Hits, Vol. 1 album.

1. “Heads Carolina, Tails California” 

Written by Tim Nichols, Mark D. Sanders (1996) 

In 1996, Messina made her country radio debut with her breakout hit, “Heads Carolina, Tails California.” The song made its way up the charts into the Top 10 and introduced fans to Messina’s feisty and fun personality. The tune, which uses the idea of flipping a coin with a loved one to select a destination, also paved the way for Messina’s second hit, “You’re Not in Kansas Anymore.”