About the song
Earl Thomas Conley’s song “Can’t Win for Losing You” encapsulates the essence of heartache and longing with its soulful melody and introspective lyrics. Written by Bob McDill and Dickey Lee, this track was featured on Conley’s 1987 album “The Heart Holds On,” adding to his repertoire of emotionally charged country ballads.
Born on October 17, 1941, in Portsmouth, Ohio, Earl Thomas Conley carved out a niche in the country music scene with his distinctive blend of soulful vocals and heartfelt storytelling. “Can’t Win for Losing You” showcases Conley’s ability to convey the complexities of love and loss, resonating deeply with audiences who appreciate lyrical depth and emotional honesty.
Released as a single, “Can’t Win for Losing You” climbed the charts, demonstrating its popularity and Conley’s enduring appeal. Throughout his career, Conley earned numerous accolades and chart-topping hits, including songs like “Holding Her and Loving You,” “Once in a Blue Moon,” and “What I’d Say.” These achievements solidified his reputation as a formidable force in country music during the 1980s.
“The Heart Holds On,” the album that features “Can’t Win for Losing You,” further cemented Conley’s status as a prolific artist capable of capturing the nuances of human emotion through his music. His songs often explore themes of heartbreak, redemption, and personal reflection, making him a relatable figure for listeners seeking authenticity in country music.
In summary, “Can’t Win for Losing You” by Earl Thomas Conley is a testament to his ability to evoke profound emotions through music. With its poignant lyrics and soulful delivery, the song remains a cherished part of Conley’s legacy, highlighting his enduring impact on country music and his ability to connect with audiences on a deep, emotional level.
Video
Lyrics
Hey, how have you been?
Good to see you again
Gee, it’s been a long time
How’s that new man
Momma and Dad
Since I told you goodbye?
Now I’m still the same
Still raisin’ Cain
Nobody’s worried ’bout me
I come and I go, just as I please
Since I set myself free
But I can’t win for losin’ you
I just can’t get over you
Bein’ footloose and fancy free
Ain’t all it’s cracked up to be
And the grass ain’t no greener
Here on the other side
I might win a heart or two
But I can’t win for losin’ you
Well I’m on my way, there’s so much to say
Lord knows that I’ve had my time
But girl, you can bet I’ll never forget
When you used to be mine
But I can’t win for losin’ you
I just can’t get over you
Bein’ footloose and fancy free
Ain’t all it’s cracked up to be
And the grass ain’t no greener
Here on the other side
I might win a heart or two
But I can’t win for losin’ you
No I can’t win for losin’ you
I just can’t get over you
Bein’ footloose and fancy free