I Listened to Every No. 1 Country Song From 1989 and These Are the Best Ones

The year 1989 was full of country classics. Here are a few of the best songs that went No. 1 that year, that still get stuck in our heads from time to time.

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“If Tomorrow Never Comes” by Garth Brooks

In the 90s, Garth Brooks would make a name for himself as one of the best crossover artists of the decade. Before that, though, he had his first No. 1 with “If Tomorrow Never Comes”, which the country star wrote with Kent Blazy back when he was just a demo singer.

As Brooks explains in The Anthology Part 1, “[The song is] about this guy who wants to make sure his wife knows that if something happens to him, that he did love her. She didn’t have to wonder.”

“Why’d You Come in Here Lookin’ Like That” by Dolly Parton

This song sings about the classic phenomenon we all know a little too well: running into an ex-lover and feeling a sense of regret because they look just a little too good. 

The release of “Why’d You Come in Here Lookin’ Like That” followed the success of another Parton No. 1, “Yellow Roses” in 1989. Both songs were also featured on Parton’s 1989 album White Limozeen, which spent 100 weeks on the U.S. country albums chart.

“Two Dozen Roses” by Shenandoah

This Shenandoah song tells of a man’s regret. While it’s unclear exactly what he does to lose the affection of his partner, in this song, the narrator spends most of it wondering if there’s anything he can possibly do to win her back.

If I had two dozen roses
And an older bottle of wine
If I really could’ve hung the moon
Would it change your mind?

In 2023, the group also released a new version of the song with country singer Luke Combs, who had often covered “Two Dozen Roses” before collaborating with Shenandoah.

“In A Letter To You” by Eddy Raven

Raven’s “In A Letter To You” has that upbeat mainstream country sound, complete with an organ and a punchy beat. The song itself is pretty self-explanatory. Raven sings about sending a letter to his lover, which contains things you typically can’t put in an envelope. The sentiment is sweet, though, and as far as love songs go, this one is surprisingly fun and upbeat.

Oh, I want you to know that I took a rainbow
And sent it off in a letter to you
Took some flowers in the spring, made a sweet clover ring
And sent it off in a letter to you.

Photo by: Richard E. Aaron/Redferns