It Ain't Cool to Be Crazy About You

"It Ain't Cool to Be Crazy About You"
"It Ain't Cool to Be Crazy About You"
Single by George Strait
from the album #7
B-side	"Rhythm of the Road"
Released	August 25, 1986
Recorded	January 28, 1986
Genre	Country
Length	2:52 (album version); 2:38 (single edit);
Label	MCA 52914
Songwriters	Dean Dillon, Royce Porter
Producers	Jimmy Bowen & George Strait
George Strait singles chronology

Last updated January 27, 2026

"It Ain't Cool to Be Crazy About You" is a song written by Dean Dillon and Royce Porter, and recorded by American country music artist George Strait. It was released in August 1986 as the second and final single from his album #7 . "It Ain't Cool to Be Crazy About You" was his 9th #1 single.^[1]

Content

The narrator is a man who believed that his relationship was special but now at the end of it he now realized he was played as a fool. He recognizes his errors and how he shouldn't of gave her his heart and that he wished he listened to his friends. Throughout the song he emphasizes on how much it hurt to be crazy in love with her and he shouldn't of been so reckless with his heart.

Critical reception

Leeann Ward of Country Universe gave the song an A grade, saying that "hearing the first strains of the simple piano intro makes it almost impossible to get the tune out of your head once it’s there." She goes on to say that 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."^[2]

Cover version

Kenny Chesney has recorded a version of this song. It was only available as a B-side for his "Never Wanted Nothing More" in 2007.

Charts

"It Ain't Cool" reached number 1 on the Billboard Hot Country Songs chart and number 5 on the Canadian RPM Country Tracks chart.

Weekly charts

Chart (1986)	Peak position
US Hot Country Songs ( Billboard )^[3]	1
Canadian RPM Country Tracks	5

Year-end charts

Chart (1987)	Position
US Hot Country Songs (Billboard)^[4]	34

References

↑ Whitburn, Joel (2004). The Billboard Book Of Top 40 Country Hits: 1944-2006, Second edition. Record Research. p. 336.
↑ CountryUniverse.net Song review
↑ "George Strait Chart History (Hot Country Songs)". Billboard .
↑ "Hot Country Songs – Year-End 1987". Billboard. Retrieved June 26, 2021.

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[1] Whitburn, Joel (2004). The Billboard Book Of Top 40 Country Hits: 1944-2006, Second edition. Record Research. p. 336.

[2] CountryUniverse.net Song review

[sc_Billboardcountrysongs_George_Strait-3] "George Strait Chart History (Hot Country Songs)". Billboard .

[4] "Hot Country Songs – Year-End 1987". Billboard. Retrieved June 26, 2021.

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v t e George Strait singles
Albums Singles Ace in the Hole Band The Cowboy Rides Away Tour
1980s	"Unwound" "Down and Out" "If You're Thinking You Want a Stranger (There's One Coming Home)" "Fool Hearted Memory" "Marina del Rey" "Amarillo by Morning" "A Fire I Can't Put Out" "You Look So Good in Love" "Right or Wrong" "Let's Fall to Pieces Together" "Does Fort Worth Ever Cross Your Mind" "The Cowboy Rides Away" "The Fireman" "The Chair" "You're Something Special to Me" "Nobody in His Right Mind Would've Left Her" "It Ain't Cool to Be Crazy About You" "Ocean Front Property" "All My Ex's Live in Texas" "Am I Blue" "Famous Last Words of a Fool" "Baby Blue" "If You Ain't Lovin' (You Ain't Livin')" "Baby's Gotten Good at Goodbye" "What's Going On in Your World" "Ace in the Hole" "Overnight Success"
1990s	"Love Without End, Amen" "Drinking Champagne" "I've Come to Expect It from You" "If I Know Me" "You Know Me Better Than That" "The Chill of an Early Fall" "Lovesick Blues" "Gone as a Girl Can Get" "So Much Like My Dad" "I Cross My Heart" "Heartland" "When Did You Stop Loving Me" "Easy Come, Easy Go" "I'd Like to Have That One Back" "Lovebug" "The Man in Love with You" "The Big One" "You Can't Make a Heart Love Somebody" "Adalida" "Lead On" "Check Yes or No" "I Know She Still Loves Me" "Blue Clear Sky" "Carried Away" "I Can Still Make Cheyenne" "King of the Mountain" "One Night at a Time" "Carrying Your Love with Me" "Today My World Slipped Away" "Round About Way" "I Just Want to Dance with You" "True" "We Really Shouldn't Be Doing This" "Meanwhile" "Write This Down" "What Do You Say to That"
2000s	"The Best Day" "Go On" "Don't Make Me Come Over There and Love You" "If You Can Do Anything Else" "Run" "Living and Living Well" "She'll Leave You with a Smile" "Tell Me Something Bad About Tulsa" "Cowboys Like Us" "Desperately" "I Hate Everything" "You'll Be There" "She Let Herself Go" "The Seashores of Old Mexico" "Give It Away" "It Just Comes Natural" "Wrapped" "How 'bout Them Cowgirls" "I Saw God Today" "Troubadour" "River of Love" "Living for the Night" "Twang"
2010s	"I Gotta Get to You" "The Breath You Take" "Here for a Good Time" "Love's Gonna Make It Alright" "Drinkin' Man" "Give It All We Got Tonight" "I Believe" "I Got a Car" "Let It Go" "Cold Beer Conversation" "Every Little Honky Tonk Bar" "The Weight of the Badge"
Other songs	"Murder on Music Row" (w/ Alan Jackson) "Hey, Good Lookin'" (w/ Jimmy Buffett, Clint Black, Kenny Chesney, Alan Jackson and Toby Keith) "Shiftwork" (w/ Kenny Chesney) "Everybody Wants to Go to Heaven"