The Captivating Tale Behind George Strait’s Hit Song “It Ain’t Cool to Be Crazy About You”
George Strait (#1, 1986)
Have you ever wondered about the stories behind your favorite songs? The creation of a song can be a fascinating journey, filled with creativity and unexpected turns. One such story revolves around George Strait’s chart-topping hit, “It Ain’t Cool to Be Crazy About You,” written by Royce Porter and Dean Dillon. Let’s dive into the captivating tale behind this beloved country classic.
Dean Dillon, the talented songwriter, had a captivating line, “it ain’t cool to be crazy about you,” playing on repeat in his mind for quite some time. However, he struggled to transform this fragment into a complete song. Instead of putting pen to paper, Dean preferred to let the rest of the lyrics develop organically in his thoughts. Nevertheless, he had made up his mind that if he ever finished the song, he would pitch it to his good friend and occasional golfing partner, George Strait.
Weeks passed, and Dean found himself at a creative impasse. Determined to bring his musical vision to life, he reached out to his friend, Royce Porter, who was also an accomplished songwriter. Dean, accompanied by his wife, paid a visit to Royce and his wife at their home. While the ladies indulged in conversation, the two men retreated to Porter’s 34-foot houseboat. Armed with a guitar, they sat on the couch, bouncing ideas off each other.
Dean shared his elusive line, “it ain’t cool to be crazy about you,” with Royce. Inspired by Dean’s words, Royce exclaimed, “Son, pass me that guitar.” They dove headfirst into the creative process, fueled by their shared passion for music. Astonishingly, within just an hour, they had transformed the initial phrase into a complete song— “It Ain’t Cool to Be Crazy About You.” Excited by their accomplishment, they rushed back to the house to share it with their wives. Royce’s wife humorously remarked, “Yeah, that’ll pay for the houseboat.”
The very next day, Dean’s publisher, Larry Butler, was so captivated by the song that he immediately organized a demo session. Larry wanted to explore every possible opportunity for this remarkable composition. Initially, he pitched the song to Mac Davis, not realizing that George Strait was the perfect artist to bring it to life. Luckily, Mac Davis passed on the tune, paving the way for George Strait to step in and make it his own.
George embraced the essence of the demo, maintaining its heartfelt charm. The subtle and melancholic piano fills, skillfully performed by John Jarvis, provided the song’s solid musical foundation. Although many, including George’s producer Jimmy Bowen, were surprised by his choice, “It Ain’t Cool to Be Crazy About You” effortlessly claimed the top spot on Billboard’s country singles chart on December 6, 1986. This remarkable achievement marked George Strait’s ninth out of an astounding 44 Billboard number one hits. Throughout his career, he would go on to accumulate a total of 60 chart-toppers, including his final hit, “Give It All We Got Tonight,” in 2012.
The story behind “It Ain’t Cool to Be Crazy About You” is a testament to the unpredictable nature of songwriting. It emphasizes the power of collaboration and the magic that can unfold when talented minds come together. As we listen to this timeless classic, let’s appreciate the journey it took to create a song that continues to resonate with country music fans around the world.

Album: #7
Artist: George Strait
Released: 1986
Lyrics
I thought you and me were something special
Thought you thought that way too
Now I know that this ol’ boy just ain’t the
Best you think you’ll ever do
It ain’t cool to be crazy about you
It ain’t suave or debonair
To let you know I care, like I do
It ain’t smart to be so reckless with my heart
I should have known right from the start
I’d end up like a fool
Believe me, it ain’t cool
All of my friends, they tried to tell me
What and what not to do
It took a while for them to sell me
But finally they got through
It ain’t cool to be crazy about you
It ain’t suave or debonair
To let you know I care, like I do
It ain’t smart to be so reckless with my heart
Should have known right from the start
I’d end up like a fool
Believe me, it ain’t cool

