Most artists can only dream of the kind of staying power George Strait has harnessed throughout his five-decade career. At 73, the “King of Country” continues to sell out stadiums and perform for record-breaking crowds. On this day in 1986, Strait found himself in a familiar position. He was back atop the country music charts for the ninth time with “It Ain’t Cool to Be Crazy About You.”
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The second and final single from his platinum 1986 album #7, “It Ain’t Cool to Be Crazy About You” was yet another Dean Dillon gem. The songwriter, who has penned nearly 70 songs for George Strait—including “Ocean Front Property” and “Here For a Good Time”—shared writing credits with Royce Porter.
As its title suggests, “It Ain’t Cool to Be Crazy About You” is the opposite of slick and unbothered. In fact, the narrator even acknowledges in the second verse that “It ain’t suave or debonair / To let you know I care, like I do.”
“While it almost seems like just a catchy ditty on the surface, Strait’s delivery of a mix of sadness and regret, with a hint of frustration, turns this song into something substantive with a relatable scenario,” wrote Leeann Ward for Country Universe in 2012.
George Strait released just two singles from #7. Both were written by Dean Dillon, and both topped the charts. “Nobody in His Right Mind Would’ve Left Her” also reached No. 1.
Kenny Chesney Covered This Song
George Strait wasn’t the only country artist to take on “It Ain’t Cool to Be Crazy About You.” In 2007, Kenny Chesney recorded his own version as a B-side for his No. 1 hit “Never Wanted Nothing More.”
And just last year, rising country star Zach Top put his throwback stamp on “It Ain’t Cool” during the Songs and Stories of Dean Dillion event at Propst Arena in Huntsville, Alabama.
Top’s performance drew praise on social media, with one TikTok user remarking that “George would approve!”
Added another, “Wow he’s amazing singing the king’s music and he passed.”
Featured image by Ralph Dominguez/MediaPunch via Getty Images
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