George Strait’s ‘It Ain’t Cool To Be Crazy About You’ #1 on Billboard Country Chart 34 Years Ago Today

by Matthew Wilson
Photo credit: CBS via Getty Images

It’s been over three decades since George Strait released his No. 1 hit “It Ain’t Cool to Be Crazy About You,” breaking hearts across the airwaves. The song first released 34 years ago.

The song speaks to unrequited love and heartbreak. Strait’s narrator thinks a girl loves him. But he soon realizes that he’s been in a one-sided relationship and she’s been treating him like a fool. The tune is the perfect material to listen to after a break-up, especially if you need a good cry. The tune features Strait at the top of his game, with poignant lyrics set to a somber melody.

Songwriter Dean Dillon Developed the Idea for the Song

For songwriter Dean Dillon, it started with a line. The phrase, “it ain’t cool to be crazy about you,” was stuck in his head for what he thought felt like forever. Often, when people get lyrics repeating in their minds, they’ll just listen to the song. But for a songwriter like Dillon, the song didn’t actually exist.

Unable to think up more lyrics, Dillon decided to phone a friend. He reached out to fellow songwriter Royce Porter for help. The two decided to have an impromptu writing session at Porter’s residence. While their wives chatted, the songwriters went out on Porter’s houseboat to try to crank out the song.

Sitting on a couch with only a guitar, the two developed the rest of the lyrics of the song. Upon hearing the lyric that plagued Dillon for weeks, Porter said, “Son, pass me that guitar.”

About an hour later, the two penned a song that Porter’s wife swore, “Yeah, that’ll pay for the houseboat.”

The Songwriters Approached George Strait

Afterward, Porter pitched the song for Mac Davis to play. But Dillon had his heart set on his golf buddy Strait performing the tune. Eventually, Dillon got his way after Davis passed on the song. Upon release, the tune became Strait’s ninth No.1 hit of his career.

Years later, Kenny Chesney would cover the song on his album “Never Wanted Nothing More” in 2007.