Our Top Country Tracks of 1999

By: Rachel Silverman


Let me take you back. The century is hurtling towards a close. No one is glued to their phone screen quite yet and your crazy conspiracy uncle is talking about something called Y2k. Yep, it’s 1999 and things seem to be a little bit simpler. Country music is in its fifth generation and competing majorly with pop boy bands and r&b. The year was a major success for country music and in 2022 we’re a bit reminiscent of it. These are our favorite songs in country music from 1999.


Cowboy Take Me Away- The Chicks

We have to start this list off with none other than The Chicks. 1999 saw the release of the trio’s sophomore album Fly and the hit “Cowboy Take Me Away”. Natalie Maines’ vocals tell the story of a yearning to be taken away from the city life to be with a true cowboy. Her voice is honest and earnest. Accompanied by Martie Maguire’s fiddle and Emily Strayer’s banjo, the song avoids tear jerking cliches in exchange for a genuinely catchy harmony that makes you smile. The song reached Number 1 on Billboard Hot Country Songs.




Right On The Money- Alan Jackson

“Right On The Money” is a charming love song that describes that feeling when you love someone. You know the one? When your world all of a sudden is a little bit brighter and more vivid and everything just feels right. “Right On the Money” was Jackson’s sixteenth number one single. The strengths of the song come from the breakdown on the keys and that extremely catchy chorus. You’ll still hear people singing “Right On the Money” at your local honky tonk.





God Must Have Spent A Little More Time On You- Alabama, *NSYNC

I know earlier I said that pop boy bands and country were competing at this time, but there were a few good things that came from their shared era. This song is one of them. “God Must Have Spent A Little More Time On You” is a cover of the NSYNC song by the same name. Randy Owens' soulful vocals drive the song and add a certain warmth to the cover that the boy band just couldn’t crack. Jeff Cook plays a sweet lick over NSYNC’s backing track that adds a classic country rock vibe to the pop ballad. The Song reached number 3 on Billboard’s Hot Country Songs.





She Thinks My Tractor’s Sexy- Kenny Chesney

The first time I heard "She Thinks My Tractor’s Sexy" I thought it was a joke and knowing Kenny Chesney’s personality, maybe it partially is. But at the same time, I can't help but fully believe him. Even if you are listening to it as a joke at first, very quickly you’ll realize the upbeat tempo of this song is actually quite catchy. Also, if you play this song at a party, you’re guaranteed to get lots of smiles and laughs. The songs may not have reached very high on the billboards during it's time, but over the years it has developed quite the cult following that has kept it playing.





These four songs may not have stayed consistently at the top of the country music charts for all of 1999, but in 2022 we’re still playing them. Our fond reminiscence of this era of country reminds us how quickly country music is evolving, and that’s not a bad thing! But still, every once in a while don’t you wish you could go back?


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